Login| Sign Up| Help| Contact|

Patent Searching and Data


Title:
POLYMERS
Document Type and Number:
WIPO Patent Application WO/2021/058970
Kind Code:
A1
Abstract:
A method of identifying a first object, the method comprises: providing a first object comprising a material, the material comprising a polymer and a luminescent compound; and detecting an absorption and/or excitation and/or emission spectrum from the luminescent compound of the first object which is indicative of the identity of the object; wherein the luminescent compound is represented by the following general formula (A): wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and/or an aliphatic group; p is an integer of 1 to 2; q and s are independently integers of 1, 2, 3, or 4; Y1, Y2, and Y3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y1, Y2, and/or Y3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

More Like This:
Inventors:
SHEPHERD, Mark (Birmingham Research ParkVincent Drive, Birmingham West Midlands B15 2SQ, GB)
PREECE, Jon (Birmingham Research ParkVincent Drive, Birmingham West Midlands B15 2SQ, GB)
ROBINSON, Alex (Birmingham Research ParkVincent Drive, Birmingham West Midlands B15 2SQ, GB)
JONES, Owen (Birmingham Research ParkVincent Drive, Birmingham West Midlands B15 2SQ, GB)
BUTLIN, Michael (Birmingham Research ParkVincent Drive, Birmingham West Midlands B15 2SQ, GB)
VIRZBICKAS, Karolis (Birmingham Research ParkVincent Drive, Birmingham West Midlands B15 2SQ, GB)
Application Number:
GB2020/052325
Publication Date:
April 01, 2021
Filing Date:
September 24, 2020
Export Citation:
Click for automatic bibliography generation   Help
Assignee:
CHROMATWIST LIMITED (Birmingham, West Midlands B31 2NB, GB)
International Classes:
C09D5/22; C09K11/06; B42D25/29; G01N21/64; G07D7/1205; C07D263/52; B41M3/14; C09K9/02; C09K11/02
Attorney, Agent or Firm:
HGF LTD (1 City Walk, Leeds Yorkshire LS11 9DX, GB)
Download PDF:
Claims:
CLAIMS

1. A method of identifying a first object, the method comprising: i. providing a first object comprising a material, the material comprising a polymer and a luminescent compound; and ii. detecting an absorption and/or excitation and/or emission spectrum from the luminescent compound of the first object which is indicative of the identity of the object; wherein the luminescent compound is represented by the following general formula (A):

(A) wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R represents an aromatic group and/or an aliphatic group; p is an integer of 1 to 2; q and s are independently integers of 1 , 2, 3, or 4;

Y1, Y2, and Y3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y1, Y2, and/or Y3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

2. A method according to Claim 1 , further comprising comparing the absorption and/or excitation and/or emission spectrum with a reference absorption and/or excitation and/or emission spectra ora database of absorption and/or excitation and/or emission spectra, e.g. comprising or consisting of absorption and/or excitation and/or emission spectra of luminescent compounds of formula (A) and combinations thereof.

3. A method according to Claim 1 or 2, comprising determining the provenance or origin of the first object.

4. A method according to any preceding Claim, comprising irradiating the first object with a light source to excite one or more luminescent compound(s) of formula (A).

5. A method of distinguishing a first object from a second object, the method comprising: i. providing a first object comprising a material, the material comprising a polymer and a luminescent compound; ii. providing a second object; iii. detecting a first absorption and/or excitation and/or emission spectrum of the first object; iv. detecting a second absorption and/or excitation and/or emission spectrum of the second object; and v. comparing the first spectrum and the second spectrum to distinguish the first object from the second object; wherein the luminescent compound is represented by the following general formula (A):

(A) wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R represents an aromatic group and/or an aliphatic group; p is an integer of 1 to 2; q and s are independently integers of 1 to 4;

Y\ Y2, and Y3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y1, Y2, and/or Y3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

6. A method according to any of Claims 5 to 9, wherein the first object comprises more than one luminescent compound of formula (A).

7. A method according to Claim 5 or 6, wherein the second object is absent the luminescent compound(s) of formula (A) of the material of the first object.

8. A method according to any one of Claim 5 to 7, comprising irradiating the first object and the second object with a light source to excite one or more luminescent compound(s) of formula (A).

9. A method according to any one of Claims 5 to 8, comprising detecting a first emission spectra and a second emission spectra, e.g. detecting a first emission maxima (Amax) and/or a second emission maxima (Amax).

10. A method according to Claim 9, comprising detecting and/or recording the first and second emission spectra in the UV/visible range of the electromagnetic spectrum, e.g. between 100 to 900 nm, e.g. from 200 to 600 nm, or from 300 to 500 nm.

11. An object comprising a material, the material comprising a polymer and one or more luminescent compound(s) represented by the following general formula (A):

(A) wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R independently represents an aromatic group and/or an aliphatic group; p is an integer of 1 to 2; q and s are independently integers of 1 to 4;

Y1, Y2, and Y3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y1, Y2, and/or Y3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

12. An object according to Claim 11, wherein the object comprises or is a document, e.g. an identification document, a passport, a driving licence, a birth certificate.

13. An object according to Claim 11 or 12, wherein the object comprises or is a form of currency, e.g. the document is bank note.

14. An object according to any of Claims 11 to 13, wherein the material comprising the polymer and one or more luminescent compound(s) is provided in the form of an ink or an adhesive or a coating ora film.

15. An object according to Claim 12 or 13, wherein the material comprising the polymer and the luminescent compound of formula (A) is provided as, or located in or on, a transparent film on the document.

16. An object according to Claim 11, wherein the object is a container or vessel, e.g. a cup, a bottle, a food container, a toiletries container.

17. An object according to Claim 11, wherein the object is a component part for use in the fabrication of a building or a vehicle, e.g. an aeroplane, a car, a boat.

18. An object according to Claim 18, wherein the object is a panel, e.g. a composite panel comprising a polymer and fibres.

19. An object according to any of Claims 11 to 18, wherein the material comprise more than one luminescent compound of formula (A), e.g. two, three, or n distinct luminescent compounds of general formula (A).

20. An object according to any of Claims 11 to 19, wherein the polymer is selected from one or more of polyvinylchloride (PVC), polyurethane (PU) (e.g. thermoplastic polyurethane (TPU)), acrylonitrile butadiene styrene (ABS), poly(methyl methacrylate) (PMMA), poly(4-vinylphenol) (PHS), polyethylene glycol (PEG), polystyrene (PS), polypropylene (PP), polyester (PE), polylactic acid (PLA), polyethylene terephthalate (PET), low density polyethylene (LDPE), and/or high density polyethylene (HDPE), or mixtures, or copolymers thereof. 21. An object according to any of Claims 11 to 20, wherein one or more, or each, of the luminescent compound(s) of formula (A) is or are present in an amount of from 10:1 to 100:0.1 by weight of polymer to luminescent compound, e.g. from between 100:1 to 100:0.1 by weight of polymer to luminescent compound.

22. A method or an object according to any preceding Claim, wherein the one or more luminescent compound(s) (A) is represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R independently represents an aromatic group and/or an aliphatic group;

Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, Y12, Y13 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein two or more of Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, Y12, Y13 combine together to form a condensed ring (e.g. a condensed aromatic ring).

23. A method or an object according to Claim 22, wherein the one or more luminescent compound(s) is represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R independently represents an aromatic group and/or an aliphatic group; q is independently an integer of 1 to 3; s is independently an integer of 1 to 4; t is independently an integer of 1 to 4;

Y2, Y3, and Y14 and J independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y1, Y2, and/or Y14 may combine together to form a condensed ring (e.g. a condensed aromatic ring). 24. A method or an object according to any of Claims 1 to 22, wherein the one or more luminescent compound (A) is represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R independently represents an aromatic group and/or an aliphatic group; A independently represents a hydrogen atom, an aryl group, an alkyl group (e.g. an alkyl ether) comprising 1 to 20 carbons (e.g. 1 to 15 carbons, or 1 to 10 carbons, or 10, 9, 8, 7, 6, 5, 4, 3, 2 or 1 carbons);

J independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein J may combine together to form a condensed ring (e.g. a condensed aromatic ring).

25. A method or an object according to any of Claims 1 to 21 , wherein the one or more luminescent compound(s) is selected from one or more of Compounds 1 to 47 according to Examples of the invention.

Description:
POLYMERS

This invention relates generally to a method of identifying and/or distinguishing objects. More specifically, although not exclusively, this invention relates to an object containing a means of identifying and/or distinguishing the object from another object, and methods of identifying and/or distinguishing the same.

Plastic is an extremely useful synthetic or semi-synthetic material used in the fabrication of many everyday objects and products. It is a material that provides many advantages over traditional materials such as glass, wood, and metal because it is durable, lightweight, and inexpensive. However, plastic waste has a significant impact on the environment. Most plastic waste degrades very slowly and persists in landfill for tens to hundreds of years, creating debris and pollution which harms wildlife within ecosystems.

It is possible to recycle many types of plastic, which may be performed by melting the polymer for reuse in a moulding process. However, it is important that the different types of plastic are sorted according to type to prevent contamination of the batch.

For recycling purposes, plastic has been broadly categorised into seven different types by the ASTM (American Society for Testing and Materials). Each of the seven types has been assigned a resin identification code, which is a symbol consisting of a number between 1 and 7 located in a triangle formed by “chasing arrows”. For example, “1” signifies that the product is made out of polyethylene terephthalate (PET), and “7” signifies that the product is made out of “other plastics” such as acrylic, nylon, polycarbonate, and polylactic acid.

Sorting plastic waste is often performed manually by identifying the resin identification code. However, this symbol may be obscured, which leads to unnecessary disposal in landfill. In addition, the broad categorisation of plastics into seven different types fails to capture the exact nature of the plastic from which the object has been fabricated. For example, polymers may be modified and/or blended to form compositions that provide different mechanical properties. Composite products may be formed from polymers combined with fibres. It is difficult to determine the composition of such materials, which presents a challenge for recycling and/or reuse of the plastic within the object. In addition, it is difficult to sort and therefore recycle black plastic. This is because black plastic containers absorb light and are often “invisible” to the detection means used in the sorting process.

It would therefore be advantageous to provide a means to sort plastic waste more effectively and/or efficiently for recycling and/or reuse.

In addition, it would be advantageous to provide a means to identify the provenance of an object fabricated from plastic. For example, it would be advantageous to provide a means to identify the provenance of an object fabricated from plastic throughout its manufacture, distribution, use, and disposal. This may provide a means to determine whether an object is genuine or counterfeit. This may also provide a means to determine the composition and/or properties of the object.

Accordingly, a first aspect of the invention provides a method of identifying a first object, the method comprising: i. providing a first object comprising a material, the material comprising a polymer and a luminescent compound; and ii. detecting an absorption and/or excitation and/or emission spectrum from the luminescent compound of the first object which is indicative of the identity of the object; wherein the luminescent compound is represented by the following general formula (A):

(A) wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R represents an aromatic group and/or an aliphatic group; p is an integer of 1 to 2; q and s are independently integers of 1 , 2, 3, or 4;

Y 1 , Y 2 , and Y 3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y 1 , Y 2 , and/or Y 3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

In embodiments, the method may further comprise comparing the absorption and/or excitation and/or emission spectrum with a reference absorption and/or excitation and/or emission spectra or a database of absorption and/or excitation and/or emission spectra, e.g. comprising or consisting of absorption and/or excitation and/or emission spectra of luminescent compounds of formula (A) and combinations thereof.

In embodiments, the method may be used to determine the provenance or origin of the first object.

The method may further comprise irradiating the first object with a light source. The light source may emit a wavelength that is suitable to excite the luminescent compound(s). For example, the wavelength used to excite the luminescent compound(s) may be in the UV range of the electromagnetic spectrum. The wavelength may be in the range of 100 to 700 nm, e.g. from 200 to 600 nm, or from 300 to 500 nm.

A further aspect of the invention provides a method of distinguishing a first object from a second object, the method comprising: i. providing a first object comprising a material, the material comprising a polymer and a luminescent compound; ii. providing a second object; iii. detecting a first absorption and/or excitation and/or emission spectrum of the first object; iv. detecting a second absorption and/or excitation and/or emission spectrum of the second object; and v. comparing the first spectrum and the second spectrum to distinguish the first object from the second object; wherein the luminescent compound is represented by the general formula (A) as stated above and the above-noted substituents.

It has been surprisingly found that the luminescent compounds represented by the general formula (A) are suitable for use in a method of identifying and/or distinguishing an object. Advantageously, the method of the invention may be used, for example, to sort recycling of polymers, e.g. different types of polymers from one another. It has been found that the luminescent compounds represented by the general formula (A) may be dissolved within a polymer matrix and/or bonded to the polymer matrix to provide a means to identify and/or distinguish an object. The luminescent compounds represented by the following general formula (A) exhibit high brightness, photoemission in the solid state, and large Stoke shifts. Moreover, the R group may be modified or tuned to provide luminescent compounds exhibiting different absorption and/or excitation and/or emission spectra dependent on the R group.

In embodiments, the method may comprise providing a second object that is absent the luminescent compound of the material of the first object. In this case, the second spectrum of the second object may be a “blank” spectrum, for example, comprising signals for only the material from which the second object is fabricated.

In alternative embodiments, the method comprises providing a second object comprising a material, the material comprising a polymer and a luminescent compound that is identical to that present in the material of the first object, but is present in second object at a different concentration to that of the material of the first object.

Advantageously, the method of the invention may be used to distinguish between a first object having a first concentration of a luminescent compound, and a second object having a second concentration of the same luminescent compound, e.g. by comparing the first and second emission spectra.

More advantageously, the method of the invention may be used to distinguish between a first object comprising the luminescent compound and a second object being absent the luminescent compound.

The method may further comprise irradiating the first object and the second object with a light source. The light source may emit a wavelength that is suitable to excite the luminescent compound(s).

In embodiments, the method comprises detecting a first absorption spectra and second absorption spectra. In alternative embodiments, the method comprises detecting a first emission spectra and a second emission spectra. The method may comprise detecting an absorption maxima and/or an emission maxima in the first and second spectra. The method may comprise detecting the relative intensity of the first spectra and the second spectra.

The method may further comprise detecting and/or recording the first and second spectra in the UV/visible range of the electromagnetic spectrum. For example, the method may comprise detecting and/or recording the first and second spectra at a wavelength in the range of 100 to 700 nm, e.g. from 200 to 600 nm, or from 300 to 500 nm.

The luminescent compound(s) may emit light in the visible spectrum, i.e. between 380 nm and 750 nm and/or may exhibit a Stokes shift of between 8000 cm 1 to 25,000cm 1 , for example, between 15,000 cm -1 to 25,000 cm 1 . In embodiments, the luminescent compound(s) may exhibit a conductivity value of 5.0 x 10 13 S cm -1 and 1.5 x 10 11 S cm -1 , for example, between 6 x 10 12 S cnr 1 and 1.5 x 10 11 S cnr 1 . The luminescent compound(s) may exhibit a photoconductivity when irradiated at 350 nm of between 1 .5 x 10 -10 S cnr 1 and 1 x 10 -3 S cnr 1 , for example, between 1 x 10 8 S cnr 1 and 1 x 10 3 cnr 1 .

In embodiments of the methods of the invention, the first object may further comprise a second luminescent compound, distinct from the first luminescent compound. In embodiments, the first object may further comprise a third luminescent compound, or an n th luminescent compound, distinct from the first and second luminescent compound.

In embodiments, the second and/or third and/or n th luminescent compound may be a compound distinct from the luminescent compound represented by the general formula (A). For example, the second and/or third luminescent compound may be a polycyclic aromatic hydrocarbon compound, for example, selected from one of fluorescein, eosin, rhodamine, or an analogue thereof. In alternative embodiments, the second luminescent compound is represented by the general formula (A) and is distinct from the structure of the first luminescent compound. In embodiments, the third luminescent compound is represented by the general formula (A) and is distinct from the structure of the first luminescent compound and the second luminescent compound.

Advantageously, the use of different combinations and/or concentrations of distinct first, second, and/or third luminescent compounds, e.g. represented by the general formula (A), provides a bespoke and/or distinct absorption and/or emission spectrum. A specific combination of luminescent compounds may be used in the methods of the invention as a signature or an identifier for the first object, e.g. to determine its provenance and/or to distinguish the first object from the second object.

More advantageously, different combinations of luminescent compounds according to general formula (A) may be capable of absorbing light at approximately the same wavelength but emitting light at different wavelengths. In other words, the Amax of the compounds is different. This is advantageous since it enables the use of a single laser to excite the compounds whilst providing a “signature” emission spectrum.

A yet further aspect of the invention provides an object comprising a material, the material comprising a polymer and one or more luminescent compound(s) represented by the general formula (A) and the above-noted substituents.

In embodiments, the object is a document, for example, an identification document, e.g. a passport, a driving licence, a birth certificate. In embodiments, the document represents currency, e.g. the document may be a bank note. For example, the object may comprise a transparent window fabricated from the material comprising a polymer and one or more luminescent compound(s).

Advantageously, the one or more luminescent compound(s) may be usable to identify the authenticity of the document, e.g. by providing a signature emission spectra.

In some embodiments, the material of the object may comprise a first luminescent compound of general formula (A) which emits at first wavelength (i.e. having a first Amax) and a second luminescent compound of formula (A) which emits at a second wavelength (i.e. having a second Amax) which is higher than the first wavelength, wherein both the first and second compounds are capable of absorbing at a third wavelength which is lower than both the first and second wavelengths.

In some embodiments, the second wavelength (the second Amax) is at least 5%, at least 10% or at least 15% higher than the first wavelength (the first Amax). This enables the two emissions of the first and second compounds to be easily distinguished.

In some embodiments, both the first and second compounds are capable of absorbing light having a wavelength of 355 nm. In further embodiments, only one of the first and second compounds is capable of absorbing light having a wavelength of 405 nm.

Examples of pairs of luminescent compounds having the above-described properties are:

• Compound 45 and Compound 12 of the Table in Figure 9

• Compound 45 and Compound 3 of the Table in Figure 9

• Compound 22 and Compound 3 of the Table in Figure 9

In alternative embodiments, the object is a container or vessel, e.g. a cup, a bottle, a food container, a toiletries container.

In alternative embodiments, the object is a component part, for example, for use in the fabrication of a building or a vehicle, e.g. an aeroplane, a car, a boat. In embodiments, the object is a panel, e.g. a composite panel comprising a polymer and fibres.

Advantageously, the luminescent compound(s) or combinations thereof may provide, for example, information about the provenance of the component part and/or whether it meets specific safety requirements. In embodiments, the luminescent compound(s) may be dissolved in the polymer matrix. Additionally or alternatively, the luminescent compound(s) may be covalently bonded to or within the polymer chains. For example, the luminescent compound(s) may be present in the backbone of the polymer and/or in a pendant chain and/or as a pendant moiety.

In embodiments, the object or a part thereof may be fabricated from the polymer and the luminescent compound(s). Alternatively, the polymer may be present as an ink or a coating or a film on the object.

In alternative embodiments, the object may consist of an ink or a coating or a film, comprising a polymer and one or more luminescent compounds having the general formula (A).

In all aspects of the invention, the polymer may be selected from one or more of polyvinylchloride (PVC), polyurethane (PU) (e.g. thermoplastic polyurethanes (TPU)), acrylonitrile butadiene styrene (ABS), poly(methyl methacrylate) (PMMA), poly(4-vinylphenol) (PHS), polyethylene glycol (PEG), polystyrene (PS), polypropylene (PP), polyester (PE), polylactic acid (PLA), polyethylene terephthalate (PET), low density polyethylene (LDPE), and/or high density polyethylene (HDPE), or mixtures, or copolymers thereof.

In embodiments, the material comprising a polymer and one or more luminescent compounds may comprise further components, e.g. reinforcing fibres, additives, colourants.

In embodiments, one or more, or each, of the luminescent compound(s) is or are present in an amount of from 10:1 to 100:0.01 by weight of polymer to luminescent compound, for example, from 100:1 to 100:0.1 by weight of polymer to luminescent compound.

In some embodiments, the object may further comprise a biological sample, e.g. tissue and/or cells and/or a fluid such as blood. Advantageously, the luminescent compounds present in the object of the invention may be excited using multiphoton imaging techniques such as multiphoton microscopy. As is known in the art, in multiphoton microscopy (also known as two-photon microscopy) two or more photons of light are absorbed for each excitation. This technique differs from traditional fluorescence microscopy in which the excitation wavelength is shorter than the emission wavelength. Two-photon excitation microscopy typically uses near-infrared excitation light. In some embodiments, multiphoton microscopy is carried out by irradiating the subject, tissue or fluid using a light source which emits a wavelength in the range of from 500 to 1000 nm, or from 800 to 900 nm. The use of multiphoton microscopy is advantageous since it uses lower energy light and is thus less damaging to biological samples. More advantageously, the light penetrates further through tissue and is less likely to photo bleach the luminescent compound.

In embodiments, the luminescent compound(s) (A) may be represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R independently represents an aromatic group and/or an aliphatic group;

Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein two or more of Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 combine together to form a condensed ring (e.g. a condensed aromatic ring).

In embodiments, the luminescent compound(s) may be a triphenylene derivative. In alternative embodiments, the luminescent compound(s) may comprise a fused polycyclic aromatic hydrocarbon comprising six 6-mem bered rings.

In embodiments, Y 8 represents an oxygen atom and Y 9 represents a nitrogen atom, Y 8 and Y 9 being bonded to form an oxazole moiety comprising an R group selected from an aromatic group and/or an aliphatic group.

In embodiments, Y 5 and Y 6 represent carbon atoms that combine together to form a condensed ring, e.g. a condensed aromatic ring.

In embodiments, the luminescent compound(s) may be represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R independently represents an aromatic group and/or an aliphatic group; q is independently an integer of 1 to 3; s is independently an integer of 1 to 4; t is independently an integer of 1 to 4;

Y 2 , Y 3 , and Y 14 and J independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y 1 , Y 2 , and/or Y 14 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

In embodiments, the luminescent compound(s) may be represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R independently represents an aromatic group and/or an aliphatic group;

Y 15 , gΐ6_ U 17_ U 18_ gΐ9_ gSo g2ΐ_ g22_ g23_ g24_ g25_ U 2b j ndependent | y represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein more of Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 combine together to form a condensed ring (e.g. a condensed aromatic ring).

In embodiments, Y 21 represents an oxygen atom and Y 22 represents a nitrogen atom, Y 21 and Y 22 being bonded to form an oxazole moiety comprising an R group selected from an aromatic group and/or an aliphatic group.

In embodiments, the luminescent compound(s) are represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R independently represents an aromatic group and/or an aliphatic group;

A independently represents a hydrogen atom, an aryl group, an alkyl group (e.g. an alkyl ether) comprising 1 to 20 carbons (e.g. 1 to 15 carbons, or 1 to 10 carbons, or 10, 9, 8, 7, 6, 5, 4, 3, 2 or 1 carbons);

J 1 , J 2 , J 3 , J 4 , J 5 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein J 1 and J 2 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

In embodiments, A independently comprises or consists of an alkyl group, for example, a straight chain alkyl group. In embodiments, A is independently selected from one or more of a CH3, C 2 H5, C3H7, C4H9, C5H11, C6H13, C7H15, OCeHi7, C9H19, or C10H21 group. In embodiments, A may independently represent C5H 11 and/or C 4 H9.

In embodiments, A may independently represent a polyethylene glycol (PEG) group (e.g. C2H4OC2H4OC2H4OCH3). In embodiments, A may independently represent an alkyl group comprising a reactive functional group FG, for example, A may independently represent an alkyl group comprising a carboxylic acid moiety, an ester, an azide, an amine, a maleimide, and/or a thiol moiety. In embodiments, A independently represents -(CF CP O^CPhCP FG or (CF CP O^CP FG moiety, wherein FG is selected from one of a carboxylic acid moiety, an ester, an azide, an amine, a maleimide, and/or a thiol moiety.

In embodiments, X represents an oxygen atom. In embodiments, X represents a sulphur atom.

In embodiments, J 1 , J 2 , J 3 , J 4 , J 5 independently represent a hydrogen atom or a deuterium atom. In embodiments, R represents an aliphatic group or moiety. In embodiments, R represents an aromatic group or moiety.

In embodiments, the triphenylene derivative may not be the compound wherein A is C5H11, J is H and R is C4H9.

In embodiments, the luminescent compound(s) are represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R 1 and R 2 independently represents an aromatic group and/or an aliphatic group; p and q are independently an integer of 1 to 2; s is an integer of 1 to 4;

Y 1 , Y 2 , and Y 3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y 1 , Y 2 , and/or Y 3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

In embodiments, the luminescent compound(s) are represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R 1 and R 2 independently represents an aromatic group or an aliphatic group;

A independently represents a hydrogen atom, an aryl group, an alkyl group (e.g. an alkyl ether) comprising 1 to 20 carbons (e.g. 1 to 15 carbons, or 1 to 10 carbons, or 10, 9, 8, 7, 6, 5, 4, 3, 2 or 1 carbons);

J 1 , J 2 , J 3 , J 4 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein J 1 and J 2 may combine together to form a condensed ring (e.g. a condensed aromatic ring). In all embodiments, the term “condensed ring” is intended to define groups that bond together to form a ring (e.g. an aromatic ring, and/or a heterocyclic ring) that forms part of the core of the luminescent compound, that is, to expand the triphenylene core.

In embodiments, A may independently represent CsHu and/or C4H9. In embodiments, A may independently represent a polyethylene glycol (PEG) group (e.g. C2H4OC2H4OC2H4OCH3). In embodiments, A may independently represent an alkyl group comprising a reactive functional group FG, for example, A may independently represent an alkyl group comprising a carboxylic acid moiety, an ester, an azide, an amine, a maleimide, and/or a thiol moiety. In embodiments, A independently represents -(CH 2 CH 2 0) 2 CH 2 CH 2 FG or (CF CF O^CF FG moiety, wherein FG is selected from one of a carboxylic acid moiety, an ester, an azide, an amine, a maleimide, and/or a thiol moiety.

In embodiments, the luminescent compound(s) are represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R 1 , R 2 , R 3 independently represent an aromatic group or an aliphatic group; p, q, and s are each independently an integer of 1 to 2;

Y 1 , Y 2 , and Y 3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein Y 1 , Y 2 , and/or Y 3 may combine together to form a condensed ring (e.g. a condensed aromatic ring).

In embodiments, the luminescent compound(s) are represented by the following general formula: wherein X represents one of a nitrogen atom, an oxygen atom, a sulphur atom, a phosphorus atom, or a selenium atom;

R 1 , R 2 , R 3 independently represent an aromatic group or an aliphatic group;

A independently represents a hydrogen atom, an aryl group, an alkyl group (e.g. an alkyl ether) comprising 1 to 20 carbons (e.g. 1 to 15 carbons, or 1 to 10 carbons, or 10, 9, 8, 7, 6, 5, 4, 3, 2 or 1 carbons);

J independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyglycol group (e.g. a group comprising a polyethylene glycol moiety), an oxygen atom (e.g. a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g. a primary, secondary, or tertiary amine group), a cyano group, a nitro group; and/or wherein J may combine together to form a condensed ring (e.g. a condensed aromatic ring).

In embodiments, A comprises further functionality, for example, A may further comprise fluorine atoms, chlorine atoms, cyano groups, nitro groups, glycol, alkoxy, thioalkoxy, polyethylene glycol, amino, acetate, carboxylic acid, amide, thioamide, thioester, azo, and/or silyl groups. In embodiments, A comprises a functional group capable of forming a covalent bond with a second molecule, e.g. a biomolecule or a small molecule, for example, a drug molecule. The functional group may be selected from, for example, a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, an aldehyde, and/or an aliphatic alcohol. In embodiments, the functional group may be located at the terminus of one or more of A.

In embodiments, X represents an oxygen atom. In embodiments, X represents a sulphur atom.

In embodiments, A independently comprises or consists of an alkyl group, for example, a straight chain alkyl group. In embodiments, A is independently selected from one or more of a Chta, C2H5, C3H7, C4H9, CsHu, OQHI3, C7H15, OCeHi7, C9H19, or C10H21 group.

In embodiments, J, J 1 , J 2 , J 3 , J 4 , J 5 independently represent a hydrogen atom.

In embodiments, J, J 1 , J 2 , J 3 , J 4 , J 5 independently represent a deuterium atom.

In embodiments, J, J 1 , J 2 , J 3 , J 4 , J 5 independently represent a heteroatom (e.g. a nitrogen atom, an oxygen atom, a halogen, e.g. F, Cl, Br, I).

In embodiments, J comprises or represents an aryl group, e.g. a phenol group. Additionally or alternatively, J comprises a halogen atom, e.g. fluorine, chlorine, bromine, or iodine.

In embodiments, R, R 1 , R 2 , or R 3 independently represents an aliphatic group or moiety. In embodiments, R, R 1 , R 2 , or R 3 independently represents an aromatic group or moiety.

Y 1 to Y 26 and/or A or and/or J, J 1 , J 2 , J 3 , J 4 , J 5 may comprise a carboxylic acid group, a glycol, an alkoxy, a thioalkoxy, an amino, an acetate, an amide, a thioamide, a thioester, an azo, and/or a silyl group. In embodiments, one or more of Y 1 to Y 26 may comprise afunctional group capable of forming a covalent bond with a second molecule, e.g. a biomolecule or a small molecule, for example, a drug molecule. The functional group may be selected from, for example, a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, an aldehyde, and/or an aliphatic alcohol. Additionally or alternatively, Y 1 to Y 26 may comprise an alkyl group. The alkyl group(s) may be a straight chain, or may comprise a branched chain, and/or may be further functionalised. Additionally or alternatively, Y 1 to Y 26 may comprise an aryl group. The aryl group(s) may be unsubstituted or may be further functionalised.

In embodiments, R, R 1 , R 2 , or R 3 may be an alkyl group, for example, a straight or branched alkyl chain. In embodiments, at least one of R, R 1 , R 2 , R 3 may be a methyl, ethyl, propyl, butyl group.

In embodiments wherein R, R 1 , R 2 , and/or R 3 is an aromatic group, the aromatic group may be one of, or a combination of, an aromatic hydrocarbon group, and/or an aromatic heterocyclic group.

In embodiments wherein R, R 1 , R 2 , and/or R 3 is an aromatic hydrocarbon group, the aromatic hydrocarbon group may comprise one of, or a combination of, a phenyl ring and/or a substituted phenyl ring. There may be one, two, three, four, or five additional substituents on the phenyl ring. The substituents are bonded directly to the phenyl ring, and may be one of, or a combination of, fluorine, chlorine, bromine, iodine, a hydroxyl group, an amine group, a nitro group, an alkoxy group, a carboxylic acid, an amide, a cyano group, a trifluoromethyl, an ester, an alkene an alkyne, an azide, an azo, an isocyanate, a ketone, an aldehyde, an alkyl group consisting of a hydrocarbon chain, or a hydrocarbon ring, an alkyl group consisting of other heteroatoms such as fluorine, chlorine, bromine, iodine, oxygen, nitrogen, and/or sulphur. The alkyl group may comprise a hydroxyl group, an amine group, a nitro group, an ether group, a carboxylic acid, an amide, a cyano group, trifluoromethyl, an ester, an alkene an alkyne, an azide, an azo, an isocyanate, a ketone, an aldehyde, for example. The substituents may be another aromatic group, for example, R may comprise a phenyl substituted with a further phenyl ring. In embodiments, the R 1 , R 2 , and/or R 3 group may be a phenyl ring, substituted with a second phenyl ring, which in turn is substituted with a third phenyl ring. In embodiments, R, R 1 , R 2 , and/or R 3 may represent a p-fluorophenyl group, a m- fluorophenyl group, an o-fluorophenyl group, a thiophene group, a cyanophenyl moiety (e.g. a p- cyanophenyl moiety), a trifluoromethylphenyl moiety (e.g. a p-trifluoromethylphenyl moiety), an iodophenyl moiety (e.g. an o-iodophenyl moiety), a chlorophenyl moiety (e.g. an o-chlorophenyl moiety), a bromophenyl moiety (e.g. an o-bromophenyl moiety), an aminophenyl moiety (e.g. a mono-substituted or di-substituted or trisubstituted aminophenyl moiety), a nitrophenyl moiety (e.g. a p-nitrophenyl moiety), a phenol moiety.

In embodiments wherein R, R 1 , R 2 , and/or R 3 is an aromatic group, the aromatic group may be a polycyclic aromatic hydrocarbon, for example, naphthalene, anthracene, phenanthrene, tetracene, chrysene, triphenylene, pyrene, pentacene, benzo[a]pyrene, corannulene, benzo[ghi]perylene, coronene, ovalene, fullerene, and/or benzo[c]fluorene. The R 1 , R 2 , and/or R 3 group may be bonded to the triphenylene derivative by any isomer of the polycyclic aromatic hydrocarbons described, for example, 1-napthalene, 2-napthalene, 2-anthracene, 9-anthracene. The polycyclic aromatic hydrocarbon group may be substituted with other moieties such as aryl groups, alkyl groups, heteroatoms, and/or other electron withdrawing or electron donating groups.

In embodiments wherein R, R 1 , R 2 , and/or R 3 is an aromatic heterocyclic group, the heterocyclic group may be a three membered ring, a four membered ring, a five membered ring, a six membered ring, a seven membered ring, an eight membered ring, a nine membered ring, a ten membered ring, or a fused ring. In embodiments, the heterocyclic group may be furan, benzofuran, isobenzofuran, pyrrole, indole, isoindole, thiophene, benzothiophene, benzo[c]thiophene, imidazole, benzimidazole, purine, pyrazole, indazole, oxazole, benzoxazole, isoxazole, benzisoxazole, thiazole, benzothiazole, pyridine, quinoline, isoquinoline, pyrazine, quinoxaline, acridine, pyrimidine, quinozoline, pyridazine, cinnoline, phthalazine, 1 ,2,3-triazine, 1 ,2,4-triazine, 1 , 3, 5-triazine. pyridine or thiophene.

In embodiments wherein R, R 1 , R 2 , and/or R 3 is an aliphatic group, the aliphatic group may be one of, or a combination of, an n-alkyl chain, a branched alkyl chain, an alkyl chain comprising unsaturated moieties, an alkyl chain comprising heteroatoms, for example, fluorine, chlorine, bromine, iodine, oxygen, sulphur, nitrogen. The alkyl chain may comprise unsaturated portions, comprising alkenes, or aromatic moieties. The alkyl chain may comprise functional groups for further derivatisation of the polycyclic aromatic hydrocarbon, e.g. triphenylene, derivative. For example, the functional groups may be one or more of an azide, a carbonyl group, an alcohol, a halogen, an alkene, or a thioacetate.

In embodiments, R, R 1 , R 2 , and/or R 3 comprise a crown ether.

The luminescent compound(s) used in the methods of the invention may be one or more of, and any of, Compounds 1 to 47 according to Examples of the invention.

Within the scope of this application it is expressly intended that the various aspects, embodiments, examples and alternatives set out in the preceding paragraphs, in the claims and/or in the following description and drawings, and in particular the individual features thereof, may be taken independently or in any combination. That is, all embodiments and/or features of any embodiment can be combined in any way and/or combination, unless such features are incompatible. For the avoidance of doubt, the terms “may”, “and/or”, “e.g.”, “for example” and any similar term as used herein should be interpreted as non-limiting such that any feature so-described need not be present. Indeed, any combination of optional features is expressly envisaged without departing from the scope of the invention, whether or not these are expressly claimed. The applicant reserves the right to change any originally filed claim or file any new claim accordingly, including the right to amend any originally filed claim to depend from and/or incorporate any feature of any other claim although not originally claimed in that manner.

To further exemplify the invention, reference is also made to the following non-limiting Examples, in which reference to the accompanying drawings:

Figure 1 is an emission spectra of Compound 3 in poly(methyl methacrylate) according to an Example of the invention;

Figure 2 is an emission spectra of Compound 2 in poly(methyl methacrylate) according to an Example of the invention;

Figure 3 is an emission spectra of Compound 3 in poly p-hydroxystyrene (PHS) according to an Example of the invention;

Figure 4 is an emission spectra of Compound 3 in polyethylene glycol according to an Example of the invention;

Figure 5 is an emission spectra of Compound 3 in polystyrene according to an Example of the invention;

Figure 6 is an emission spectra of fluorescein in PMMA according to a Comparative Example of the invention;

Figure 7 is a graph showing the emission peak (nm) vs. the relative ratio of Compound 3 in PMMA;

Figure 8A shows a photograph of a polymer doped with Compound 2 according to an Example of the invention;

Figure 8B shows a photograph of the emission of the doped polymer of Figure 8A;

Figure 9 is a table listing the chemical structures of the luminescent molecules that may be used in embodiments of the invention; and

Figure 10A and 10B show the structures of the Precursor compounds used to synthesise the luminescent compounds of Figure 9.

The following compounds were synthesised for use in the Examples of the invention. All compound names were generated using ChemDraw (RTM) software.

Method of synthesising Compound 1

Compound 1 was synthesised using the following method from Precursor 1.

Precursor 1 was fabricated according to the method described in N. Boden et. al. J. Mater. Chem., 1995, 5, 2275.

A solution of Precursor 1 (100 mg; 0.13 mmol) in o-xylene (8 mL) was added to a flask. This was then heated and held at 175 °C for 16 h to afford Compound 1 (51% yield).

In the alternative, Compound 1 was synthesised using the following method. A solution of Precursor 1 (100 mg; 0.13 mmol) in dry PhMe (8 mL) was added to a flask containing rhodium octanoate dimer (8 mg; 0.01 mmol), under a N2 atmosphere. This was then heated and held at reflux for 20 h. The reaction was cooled to room temperature and then evaporated to dryness in vacuo, the solid was then purified via flash column chromatography (silica; 95 % n- hexane: 5 % ethyl acetate) to afford Compound 1 as a white solid (96 mg, 99 %).

The name for Compound 1 is 8-butyl-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole.

Compound 1 had the following characterisation data: 1 H NMR (300 MHz, CDCh) 6H: 10.01 (1 H, s), 7.94 (1H, s), 7.90 (1 H, s), 7.88 (1 H, s), 7.85 (1 H, s), 4.42 (2H, t, J 6.7 Hz), 4.37 (2H, t, J 6.7 Hz) 4.29 - 4.23 (6H, m), 3.09 (2H, t, J 7.5 Hz), 2.05 - 1.92 (10H, m), 1.62 - 1.43 (24H, m), 1.06 - 0.96 (18H, m) ppm. 13 C NMR (100 MHz, CDCh) 5c: 165.6, 149.5, 149.1 , 148.7, 148.3, 142.9, 140.1 , 139.8, 124.6, 123.9, 123.5, 123.3, 116.3, 111.0, 108.3, 106.9, 106.8, 102.6, 69.9, 69.6, 69.5, 68.8, 29.2, 29.0, 28.8, 28.4, 28.3, 22.6, 22.4, 14.2, 13.9 ppm. ES+MS m/z: 756.5 ([M + H] + 15 %), 778.5 ([M + Na] + 100 %). IR l 1 (neat): 3112w (C-H), 2953m (C-H), 1617w (C=N), 1517w (benzene ring), 1259s (C-O), 1177s (C-O), 1159s (C-O) cm-1. Elemental analysis Found: C, 76.09; H, 9.17; N, 1.95 %. C4BH69NC>6 requires C, 76.25; H, 9.20; N, 1.85 %. Method of synthesising Compound 2

Compound 2 was synthesised using the following method from Precursor 2.

Precursor 2 was fabricated according to the method described in N. Boden et. al. J. Mater. Chem., 1995, 5, 2275.

A slurry of benzoic acid (160 mg; 1.31 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.16 mmol) in PhMe (5 mL) was heated at 70 °C under is for 20 min. Precursor 2 (100mg, 0.13 mmol) in PhMe (2 mL) was added and the reaction was heated and held at reflux for 72 h. The mixture was cooled to room temperature and diluted with CH2CI2 (20 mL). The mixture was washed with 1 M NaOH (2 x 20 mL) and the organic phase was dried in vacuo. The crude black solid was purified via flash column chromatography (40% CH2CI2: 60 % n-hexane:) to afford Compound 2 as a white solid (35 mg, 34 %).

The name for Compound 2 is 2,3,6,11 ,12-pentakis(pentyloxy)-8-phenyltriphenyleno[1,2-d]oxazole.

Compound 2 had the following characterisation data: 1 H NMR (300 MHz, CDCh) 6H: 10.13 (1 H, s), 8.40 - 8.37 (2H, m), 7.92 (1 H, s), 7.88 (1 H, s), 7.87 (1H,s), 7.77 (1H, s), 7.57-7.55 (1H, m), 4.48 - 4.43 (4H, m), 4.30 - 4.23 (6H, m), 2.12 - 1.92 (10H, m), 1 .69 - 1.54 (12H, m), 1.53 - 1.45 (12H, m), 1.04 - 0.96 (18H, m) ppm. 13 C NMR (100 MHz, CDCh) 6c: 161.4, 149.5, 149.0, 148.7, 148.3, 142.9,

140.5, 140.2, 131.2, 128.9, 127.5, 127.1, 124.7, 123.8, 123.4, 123.3, 116.4, 110.9, 108.2, 106.8,

106.6, 103.8, 69.8, 69.5, 68.9, 29.2, 29.0, 28.4, 28.3, 22.6, 22.6, 14.1 ppm. ES+MS m/z : 775.5 ([M] + 22 %), 776.5 ([M+H] + 37 %), 798.5 ([M+Na]+ 100 %). Elemental analysis Found: C, 77.46; H, 8.44;

N, 1.75 %. CsoHssNOs requires C, 77.38; H, 8.44; N, 1.80 %.

Method of synthesising Compound 3

Compound 3 was synthesised using the following method. A solution of 2-naphthalene carboxylic acid (225 mg, 1.31 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in PhMe (5 mL) was heated at 70 °C under N2 for 20 min. A solution of Precursor 2 (100mg;

O.131 mmol) in PhMe (2 mL) was added and heated under reflux for 48-72 h, whilst stirring. The solution was cooled to room temperature and diluted with CH2CI2 (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2 x 20 mL), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n- hexane) to afford Compound 3 as a yellow solid (35 mg, 32 %).

The name for Compound 3 is 8-(naphthalen-2-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyl eno[1 ,2- djoxazole.

Compound 3 had the following characterisation data: 1 H NMR (300 MHz, CDCh) 6H: 10.22 (1 H, s), 8.89 (1H, s), 8.49 (1 H, dd, J 8.6, 1.7 Hz), 8.05 - 7.99 (2H, m), 7.96-7.91 (5H, m), 7.62 - 7.59 (2H, m), 4.54 (2H, t, J 6.8 Hz), 4.51 (2H, t, J 6.8 Hz), 4.32 - 4.25 (6H, m), 2.17 - 1.93 (10H, m), 1.76 - 1.42 (20H, m), 1 .06 - 0.97 (15H, m) ppm. 13 C NMR (100 MHz, CDCh) 6c: 161.7, 149.8, 149.3, 149.0,

148.6, 143.2, 140.9, 140.6, 135.0, 133.4, 129.3, 128.9, 128.3, 128.0, 127.9, 127.4, 127.2, 125.0, 125.0, 124.4, 124.2, 123.7, 123.6, 116.7, 111.2, 108.5, 107.1 , 107.0, 103.9, 70.2, 70.1, 69.8, 69.2,

29.6, 29.5, 28.9, 28.8, 28.7, 23.1, 23.0, 14.6, 14.5 ppm. MALDI+ m/z: 825.5 ([M] + 100%). IR A-1 (neat): Elemental analysis Found: C, 78.95; H, 8.02; N, 1.83 %. C54H67NO6 requires C, 78.51 ; H, 8.17; N, 1.70 %.

Method of synthesising Compound 4

Compound 4 was synthesised using the following method. A solution of 1 -naphthalene carboxylic acid (225 mg, 1.31 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in PhMe (5 mL) was heated at 70 °C under N2 for 20 min. A solution of Precursor 2 (100mg; 0.131 mmol) in PhMe (2 mL) was added and heated under reflux for 48-72 h, whilst stirring. The solution was cooled to room temperature and diluted with CH2CI2 (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2 x 20 mL), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n- hexane) to afford Compound 4 as a yellow solid (24 mg, 22 %). The name for Compound 4 is 8-(naphthalen-1-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyl eno[1,2- d]oxazole.

Compound 4 had the following characterisation data: 1 H NMR (300 MHz, CDCb) 6H: 10.15 (1 H, s), 9.82 (1H, d, J 8.3 Hz ), 8.59 (1 H, dd, J 7.3, 1.2 Hz), 8.08 (1 H, d, J 8.3 Hz), 8.01-7.98 (3H, m), 7.94 (2H, m), 7.71-7.61 (3 H, m), 4.54-4.45 (4H, m), 4.32-4.26 (6H, m), 2.10-1.94 (10H, m), 1.70-1.35 (20H, m), 1.04 - 0.87 (15H, m) ppm. 13 C NMR (100 MHz, CDCb) 6c: 161.3, 149.9, 149.6, 149.1 , 148.8, 143.2, 141.0, 139.9, 134.5, 132.4, 131.0, 129.6, 129.2, 127.8, 127.5, 126.9, 126.7, 125.5, 125.0, 124.2, 124.1, 123.8, 117.0, 111.0, 108.6, 107.3, 107.2, 104.4, 70.2, 69.9, 69.1 , 29.6, 29.5, 29.0, 28.8, 28.7, 23.0, 14.5 ppm. MALDI+ m/z: 826.7 ([M+H] + 100%). Elemental analysis Found: C, 78.49; H, 8.23; N, 1.73 %. C54H67NO6 requires C, 78.51; H, 8.17; N, 1.70 %.

Method of Synthesising Compound 5

Compound 5 was synthesised using the following method. A solution of 2-anthracene carboxylic acid (290 mg, 1.31 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in PhMe (5 ml_) was heated at 70 °C under N2 for 20 min. A solution of Precursor 2 (100mg; 0.131 mmol) in PhMe (2 mL) was added and heated under reflux for 48-72 h, whilst stirring. The solution was cooled to room temperature and diluted with CH2CI2 (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2 x 20 mL), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n-hexane) to afford Compound 5 as a yellow solid (22 mg, 20 %).

The name for Compound 5 is 8-(anthracen-2-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyle no[1 ,2- djoxazole.

Compound 5 had the following characterisation data: 1 H NMR (300 MHz, CDCI3) 6H: 10.20 (1 H, s), 9.00 (1H, s), 8.58 (1 H, s), 8.47 (1 H, s), 8.39 (1H, dd, J 8.9, 1.6 Hz), 8.13-8.10 (2H, m), 8.07-8.02 (2H, m), 7.93 (1 H, s), 7.90-7.89 (3H, m), 4.57 - 4.47 (4H, m), 4.31 - 4.24 (6H, m), 2.19 - 1.96 (10 H, m), 1.76 1.44(20H, m), 1.08 - 0.97 (15H, m) ppm. 13 C NMR (100 MHz, CDC ) 5c: 161.8, 149.8,

149.4, 149.0, 148.6, 143.2, 141.0, 140.6, 133.1 , 132.6, 132.3, 131.2, 129.2, 128.7 128.6, 128.2

127.4, 126.8, 126.6, 126.3, 125.0, 124.4, 124.2, 123.8, 123.6, 116.7, 111.3, 108.5, 107.1, 107.0, 104.0, 70.2, 70.1 , 69.8, 69.2, 30.1, 29.6, 29.5, 28.9, 28.8, 28.7, 23.1, 23.0, 14.7, 14.5 ppm. MALDI+ m/z: 876.5 ([M+H] + 100%). Elemental analysis Found: C, 79.49; H, 7.88; N, 1.51 %. C5BH 69 N06 requires C, 79.51 ; H, 7.94; N, 1.60 %.

Method of Synthesising Compound 6

Compound 6 was synthesised using the following method. A solution of 9-anthracene carboxylic acid (290 mg; 1.31 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in o-xylene (5 mL) was heated to 70 °C under N2 for 20 min. A solution of Precursor 2 (100mg, 0.131 mmol) in o-xylene (2 mL) was added and heated to 140 °C for 72 h. The mixture was cooled to room temperature and diluted with CH2CI2 (20 mL). The mixture was washed with 1M NaOH (2 x 20 mL) and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n- hexane) to afford Compound 6 as a yellow solid (13 mg, 11 %).

The name for Compound 6 is 8-(anthracen-9-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyle no[1,2- djoxazole.

Compound 6 had the following characterisation data: 1 H NMR (300 MHz, CDCI3) 6H: 10.18 (1 H, s), 8.70 (1H, s), 8.49 - 8.44 (2H, m), 8.15 - 8.09 (2H, m), 8.03 (1 H, s), 8.02 (1 H, s) 7.95 (1H, s), 7.94 (1H, s) 7.58 - 7.52 (4H, m), 4.50 (2H, t, J 6.7 Hz), 4.33-4.27 (6H, m), 4.17 (2 H, t, J 6.7 Hz), 2.05 - 1.93 (8H, m), 1 .79 (2H, p, J 6.7, 1 .0 Hz), 1 .66 - 1.37 (20H, m), 1 .03 - 0.92 (15H, m) ppm. 13 C NMR da: (100 MHz, CDCb) 160.6, 150.0, 149.6, 149.2, 148.8, 143.5, 141.0, 140.7, 131.9, 131.7, 131.3, 129.1, 127.7, 127.6, 126.4, 125.9 124.2, 123.8, 121.1 , 117.1 , 111.3, 108.7, 107.3, 107.2, 104.6,

70.4, 70.3, 69.9, 69.2, 29.6, 29.5, 29.0, 28.8, 28.7, 28.6, 28.5, 23.0, 22.9, 22.6, 14.5, 14.4, 14.3 ppm. MALDT m/z: 876.5 ([M+H] + 100%). Elemental analysis Found: C, 79.13; H, 7.83; N, 1.77 %. C5BH 69 N06 requires C, 79.51 ; H, 7.94; N, 1.60 %. Method of Synthesising Compound 7

Compound 7 was synthesised using the following method. A solution of 4-fluorobenzoic acid (187 mg; 1.31 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in o- xylene (5 ml_) was heated to 70 °C under N2 for 20 min. A solution of Precursor 2 (100mg, 0.131 mmol) in o-xylene (2 ml_) was added and heated to 140 °C for 72 h. The mixture was cooled to room temperature and diluted with CH2CI2 (20 ml_). The mixture was washed with 1M NaOH (2 x 20 ml_) and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n- hexane) to afford Compound 7 as a yellow solid (13 mg, 9 %).

The name for Compound 7 is 8-(4-fluorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyle no[1 ,2- d]oxazole.

Compound 7 had the following characterisation data: 1 H NMR (300 MHz; CDCI3) 6H: 10.03 (1 H, s), 8.36 - 8.30 (2H, m), 7.97 - 7.75 (4H, m), 7.28 - 7.15 (3H, m), 4.41 (4H, t, J 6.6 Hz), 4.26 (6H, m), 2.06 - 1.90 (9H, m), 1 .55 (22H, m), 1.05 - 0.95 (15H, m) ppm. 13 C NMR (100 MHz; CDC ) 5c: 166.0, 163.5, 160.6, 149.7, 149.1, 148.9, 148.5, 143.0, 140.5, 140.3, 129.8, 129.7, 127.3, 124.8, 123.9, 123.8, 123.5, 116.5, 116.3, 116.1, 111.1 , 108.4, 107.0, 106.8, 103.7, 69.9, 69.8, 69.7, 69.5, 68.9, 29.7, 29.2, 29.0, 28.5, 28.4, 28.3, 22.6, 14.2, 14.1 ppm. 19 F NMR (282 MHz, CDCb) dr: -108.0 ppm. MALDI+ m/z. 793.6 ([M] + 100 %), 794.6 ([M+H] + 55 %), 795.6 ([M+H+1] + 15 %). IR A 1 (neat): 2952m (C-H), 2926m (C- H), 2858m (C-H), 1616w (C=N), 1517s (benzene ring), 1499m (benzene ring), 1433m (benzene ring), 1261m (C-O), 1174s (C-O) cm -1 .

Method of Synthesising Compound 8

Compound 8 was synthesised using the following method. A solution of 3-fluorobenzoic acid (182 mg; 1.30 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in o- xylene (5 mL) was heated to 70 °C under N2 for 20 min. A solution of Precursor 2 (100mg, 0.131 mmol) in o-xylene (2 mL) was added and heated to 140 °C for 72 h. The mixture was cooled to room temperature and diluted with CH2CI2 (20 mL). The mixture was washed with 1M NaOH (2 x 20 mL) and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n- hexane) to afford Compound 8 as a yellow solid (13 mg, 11 %).

The name for Compound 8 is 8-(3-fluorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyle no[1,2- d]oxazole.

Compound 8 had the following characterisation data: 1 H NMR (300 MHz; CDCb) 6H: 10.06 (1 H, s), 8.15 (1H, d, J 7.9 Hz), 8.05 (1 H, dd, J 9.0, 1.9 Hz, 7.89 (4H, m), 7.53 (m, 1H), 7.36 - 7.16 (4H, m), 4.45 (4H, m), 4.33 - 4.21 (6H, m), 2.16 - 1.90 (11H, m), 1.71 - 1.39 (24H, m), 1.06 - 0.93 (15H, m ppm. 13 C NMR (100 MHz; CDCb) 5c: 164.3, 161.8, 160.1, 160.1 , 149.6, 149.1 , 148.8, 148.4, 142.9, 140.3, 140.3, 130.6, 130.5, 129.6, 129.6, 127.3, 124.8, 123.7, 123.4, 123.4, 123.2, 123.2, 118.3, 118.1, 116.4, 114.6, 114.3, 110.9, 108.2, 106.8, 106.7, 103.9, 69.9, 69.8, 69.6, 69.0, 29.4, 29.3, 29.2, 28.6, 28.5, 28.4, 22.8, 14.3 ppm. 19F NMR (282 MHz; CDCb) dr: -111.8 ppm. ES+MS m/z: 794.5 ([M] + 55%), 816.5 ([M+Na] + 100%), 817.5 ([M+H + Na] + 50%). IR A-1 (neat): 2952m (C-H), 2925m (C-H), 2856m (C-H), 1617w (C=N), 1518s (benzene ring), 1434s (benzene ring), 1262s (C- O), 1174s (C-O) cm-1. Elemental analysis Found: C, 75.62; H, 8.25; N, 1.78 %. C50H64FNO6 requires C, 75.63; H, 8.12; N, 1.76 %.

Method of Synthesising Compound 9

Compound 9 was synthesised using the following method. A solution of 2-fluorobenzoic acid (41 .86 mg; 0.26 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in o- xylene (5 mL) was heated to 70 °C under N2 for 20 min. A solution of Precursor 2 (100mg, 0.131 mmol) in o-xylene (2 mL) was added and heated to 140 °C for 72 h. The mixture was cooled to room temperature and diluted with CH2CI2 (20 mL). The mixture was washed with 1M NaOH (2 x 20 mL) and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n- hexane) to afford Compound 9 as a yellow solid (7 mg, 10 %). The name for Compound 9 is 8-(2-fluorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyle no[1 ,2- d]oxazole.

Compound 9 had the following characterisation data: 1 H NMR (300 MHz; CDCh) 6H: 10.16 (1 H, s), 8.38 (1H, m), 7.92 (4H, m), 7.63 - 7.47 (1H, m), 7.43 - 7.28 (2H, m), 4.47 (4H, m), 4.27 (5H, m), 2.13 - 1.91 (9H, m), 1.69 - 1.39 (21 H, m), 1.00 (14H, m) ppm. 13C NMR (100 MHz; CDCh) 6c:

162.4, 159.8, 157.6, 157.5, 149.7, 149.3, 148.8, 148.4,142.9, 140.6, 140.5, 139.9, 132.9, 132.8,

130.3, 127.3, 124.8, 124.5, 123.9, 123.4, 123.4, 117.4,117.2, 116.7, 116.0, 115.9, 110.9, 108.3,

107.0, 106.9, 104.4, 69.8, 69.5, 68.9, 29.2, 29.0, 28.4,28.3, 22.6, 22.6, 14.1 ppm. 19F NMR (282

MHz; CDCh) dr: -109.1 ppm. MALDI+ m/z: 793.6 ([M] + 100 %), 794.6 ([M+H] + 65 %), 795.6 ([M+1+HG 20 %) . IR A-1 (neat): 2952m (C-H), 2925m (C- H), 2856m (C-H), 1617w (C=N), 1518m (benzene ring), 1434m (benzene ring), 1261s (C-O), 1176s (C-O) cm-1. Elemental analysis Found: C, 75.92; H, 8.26; N, 1.74 %. C5oH 64 FN0 6 requires C, 75.63; H, 8.12; N, 1.76 %.

Method of Synthesising Compound 10

Compound 10 was synthesised using the following method. A slurry of Precursor 2 (100mg; 0.01 mmol), iodobenzene diacetate (51 mg; 0.16 mmol) and palladium diacetate (1 mg; 0.005 mmol) in a mixture of PhMe (5 ml_) and acetic acid (1 mL) in PhMe (5 ml_) under an N2 atmosphere was heated and held at reflux for 72 h. The reaction was then cooled to room temperature and washed with 1 M NaOH (1 M; 2 x 10mL). The organic phase was evaporated to dryness in vacuo. The solid was then purified via flash column chromatography (40 % CH2CI2: 60 % n-hexane) to afford Compound 10 as a white solid (64 mg; 66 %).

The name for Compound 10 is 8-methyl-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole.

Compound 10 had the following characterisation data: 1 H NMR 6H: (400 MHz, CDCh) 9.94 (1 H, s), 7.94 (1 H, s), 7.90 (1 H, s), 7.89 (1 H, s), 7.85 (1 H, s), 4.42 (2H, t, J 6.7 Hz), 4.38 (2H, t, J 6.8), 4.30 - 4.24 (6H, m), 2.81 (3H, s), 1.99 (10H, m), 1.65 - 1.53 (10H, m), 1.52 - 1.44 (10H, m), 1.03 - 0.96 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 162.4, 149.9, 149.4, 149.1 , 148.8, 143.2, 140.8, 140.2, 127.2, 125.0, 124.2, 123.9, 123.7, 116.7, 111 .6, 108.8, 107.3, 107.2, 102.9, 70.3, 70.2, 69.88, 69.40, 29.60, 29.5, 29.3, 28.8, 28.8, 28.6, 23.0, 15.2, 14.5 ppm. MALDI m/z : 714.5 ([M] + 100%).

Method of Synthesising Compound 11

Compound 11 was synthesised using the following method. A solution of Precursor 2 (200 mg, 0.263 mmol) and trimethylamine (0.2 mL, 1.44 mmol) in PhMe (7 mL) was heated at reflux under N2for 10 min. 2-Thiophenecarbonyl chloride (0.3 mL, 2.62 mmol) was added and heated under reflux for 90 min. The solution was cooled to room temperature and washed with 1 M HCI (30 mL) and the organic phase extracted with EtOAc (2 x 30 mL). The organic phase was dried in vacuo and the resultant black solid was heated at 240 °C for 10 min before being cooled to room temperature. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n-hexane) to afford Compound 11 as a yellow solid (136 mg; 64 %).

The name for Compound 11 is 2,3,6,11 ,12-pentakis(pentyloxy)-8-(thiophen-2-yl)triphenyleno[1 ,2- djoxazole.

Compound 11 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 10.03 (1H, s), 7.99 (1H, dd, J 3.7, 1.2 Hz), 7.92 (1 H, s), 7.89 (1 H, s), 7.88 (1 H, s), 7.88 (1 H, s), 7.58 (1H, dd, J 5.0, 1.2), 7.25 - 7.22 (1H, dd, J 5.0, 3.7 Hz), 4.48 - 4.43 (4H, m), 4.31 - 4.23 (6H, m), 2.14 - 1.93 (10H, m), 1.71 - 1.42 (20H, m), 1.04 - 0.97 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 157.8, 149.8,

149.4, 149.0, 148.6, 143.0, 140.7, 140.1, 130.6, 130.1 , 129.7, 128.5, 127.5, 125.0, 124.1, 123.7, 123.6, 116.6, 111.1 , 108.5, 107.1 , 107.1 , 104.0, 70.2, 70.2, 70.1 , 69.8, 69.1 , 29.6, 29.5, 29.4, 28.9, 28.8, 28.8, 28.6, 23.0, 23.0, 14.6, 14.5 ppm. MALDI m/z: 781.5 ([M] + 100%).

Method of Synthesising Compound 12

Compound 12 was synthesised using the following method. A solution of Precursor 2 (100 mg, 0.132 mmol), 4-Cyanobenzoyl chloride (109 mg, 0.658 mmol) and N,N-Diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 min under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 12 as a yellow solid (40 mg, 38 %).

The name for Compound 12 is 4-(2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazol-8- yl)benzonitrile.

Compound 12 had the following characterisation data: 1 H NMR dH: (300 MHz, CDCI3) 9.96 (1 H, s), 8.43 - 8.40 (2H, d, J 8.55 Hz), 7.90 (1 H, s), 7.89 (1 H, s), 7.88 (1 H, s), 7.87 (1H, s), 7.83 - 7.80 (2H, d, J 8.55), 4.43-4.38 (4H, m), 4.30 - 4.23 (6H, m), 2.12-1.93 (10H, m), 1.67 -1.42 (20H, m), 1.04 - 0.97 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDC ) 159.3, 150.0, 149.3, 149.1, 148.8, 143.1, 140.6, 140.4, 132.7, 131.4, 127.8, 127.6, 125.0, 123.7, 123.7, 123.4, 118.7, 116.6, 114.4, 111.0, 108.4, 106.9, 106.7, 104.4, 70.2, 70.0, 69.9, 69.8, 69.2, 29.6, 29.5, 29.4, 28.8, 28.8, 28.8, 28.7, 23.0, 14.6, 14.5 ppm. MALDI m/z: 800.4 ([M] + 100%).

Method of Synthesising Compound 13

Compound 13 was synthesised using the following method. A solution of 4-(trifluoromethyl)benzoic acid carboxylic acid (248 mg, 1.31 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.157 mmol) in PhMe (5 ml_) was heated at 60 °C under N2 for 30 min. A solution of Precursor 2 (100mg, 0.132 mmol) in PhMe (2 ml_) was added and heated under reflux for 48-72 h, whilst stirring. The solution was cooled to room temperature and diluted with CH2CI2 (20 ml_). The organic phase was washed with aqueous NaOH (1M; 2 x 20 ml_), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n-hexane) to afford Compound 13 as a yellow solid (6 mg; 5 %).

The name for Compound 13 is 2,3,6,11,12-pentakis(pentyloxy)-8-(4- (trifluoromethyl)phenyl)triphenyleno[1 ,2-d]oxazole.

Compound 13 had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCI3) 10.04 (1 H, s), 8.48 - 8.46 (2H, d, J 8.50), 7.92 (1 H, s), 7.90 (1 H, s), 7.89 (1 H, s), 7.88 (1H, s), 7.83 - 7.80 (2H, d, J 8.50), 4.47 - 4.45 (4H, t, J 6.74), 4.31-4.24 (6H, m), 2.14 - 1.94 (10H, m), 1.70 - 1.43 (20H, m), 1.05 - 0.98 (15H, m) ppm. 19 F NMR dr: (300 MHz, CDCb) 62.9 (s) ppm. 13 C NMR da: (100 MHz, CDCb)

159.3, 150.0, 149.3, 149.1, 148.8, 143.1, 140.6, 140.4, 132.7, 131.4, 127.8, 127.6, 125.0, 123.7, 123.7, 123.4, 118.7, 116.6, 114.4, 111.0, 108.4, 106.9, 106.7, 104.4, 70.2, 70.0, 69.9, 69.8, 69.2, 29.6, 29.5, 29.4, 28.8, 28.8, 28.8, 28.7, 23.0, 14.6, 14.5 ppm. MALDI m/z: 844.5 ([M+H] + 100%).

Method of Synthesising Compound 14

Compound 14 was synthesised using the following method. A solution of Precursor 2 (100 mg, 0.132 mmol), 2-iodobenzoyl chloride (175 mg, 0.658 mmol) and N,N-Diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 min under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 14 as a yellow solid (39.9 mg, 35 %).

The name for Compound 14 is 8-(2-iodophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno [1 ,2- djoxazole.

Compound 14 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCb) 10.07 (1H, s), 8.20 - 8.16 (1H, dd, J 7.90, 1.60 Hz), 8.18-8.15 (1H, dd, J 7.90, 1.25 Hz), 7.95 (1 H, s), 7.94 (1 H, s), 7.91 (2H, m), 7.58 - 7.53 (1H, td, J 7.66, 7.63, 1.25 Hz), 7.26 - 7.20 (1H, td, J 7.66, 7.63, 1.60 Hz), 4.52 - 4.44 (4H, m), 4.31 - 4.25 (6H, m), 2.06 - 1.94 (10H, m), 1.67-1.41 (20H, m), 1.03 - 0.92 (15H, m) ppm. 13 C NMR da: (100 MHz, CDCb) 160.9, 149.9, 149.6, 149.2, 149.1 , 143.3, 142.0, 140.6,

140.4, 132.5, 132.1, 132.1, 128.5, 127.6, 125.1 , 124.1 , 124.0, 123.7, 117.2, 111.9, 108.6, 107.3, 107.1, 104.9, 95.0, 70.4, 70.2, 70.2, 70.1 , 69.9, 29.6, 29.6, 29.5, 29.4, 28.9, 28.8, 28.7, 23.0, 23.0, 14.5 ppm. MALDI m/z: 901.6 ([M] + 14 %). Method of Synthesising Compound 15

Compound 15 was synthesised using the following method. A solution of Precursor 2 (100 mg, 0.132 mmol), 2-chlorobenzoyl chloride (175 mg, 0.658 mmol) and N,N-Diisopropylethylamine (0.1 ml_, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 min under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 15 as a yellow solid (52.4 mg, 49 %).

The name for Compound 15 is 8-(2-chlorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyle no[1 ,2- djoxazole.

Compound 15 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 10.06 (1 H, s), 8.39 - 8.34 (1H, m), 7.92 - 7.90 (4H, m), 7.66 (1 H, m), 7.51 - 7.44 (2H, m), 4.49 - 4.41 (4H, m), 4.30 - 4.25 (6H, m), 2.06 - 1.95 (10H, m), 1.67 - 1.43 (20H, m), 1 .03 - 0.92 (15H, m) ppm. 13 C NMR 5c: (100 MHz, CDCh) 158.8, 149.6, 149.4, 148.9, 148.5, 142.9, 140.4, 139.9, 133.5, 131.7, 131.6, 127.3, 127.0, 126.2, 124.8, 123.9, 123.4, 116.8, 110.9, 108.2, 106.9, 104.6, 70.1 , 70.0, 69.9, 69.6, 69.1 , 29.8, 29.3, 29.3, 29.2, 28.5, 28.4, 22.7, 14.3 ppm. MALDI m/z : 809.7 ([M] + 95 %).

Method of Synthesising Compound 16

Compound 16 was synthesised using the following method. A solution of Precursor 2 (100 mg, 0.132 mmol), 2-bromobenzoyl chloride (144 mg, 0.658 mmol) and N,N-Diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 min under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 16 as a yellow solid (25.8 mg, 21 %).

The name for Compound 16 is 8-(2-bromophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenylen o[1 ,2- d]oxazole.

Compound 16 had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCh) 10.03 (1H, s), 8.31-8.28 (1H, dd, J 7.91 , 1.75 Hz), 7.91 - 7.89 (4H, m), 7.86 - 7.83 (1H, dd, J 7.91, 1.23 Hz), 7.54 -

7.49 (1 H, td, J 7.70, 7.60, 1 .23 Hz), 7.42 - 7.37 (1 H, td, J 7.70, 7.57, 1.75 Hz) 4.49 - 4.39 (4H, m), 4.31 - 4.23 (6H, m), 2.06 - 1.95 (10H, m), 1.64 - 1.43 (20H, m), 1.03 - 0.95 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh): 159.5, 149.7, 149.4, 148.9, 148.6, 142.9, 140.3, 135.0, 132.2, 131.8, 128.3,

127.6, 127.4, 124.8, 123.9, 123.6, 123.5, 122.0, 116.9, 111.1 , 108.2, 107.0, 104.7, 70.1 , 70.0, 69.9,

69.6, 69.4, 29.3, 29.3, 29.2, 28.6, 28.5, 28.4, 22.7, 14.3 ppm. MALDI m/z : 855.7 ([M] + 31 %)

Method of Synthesising Compound 17

Compound 17 was synthesised using the following method. A solution of 5-bromovaleric acid (773 mg, 4.27 mmol), palladium diacetate (0.005 mmol) and iodobenzene diacetate (0.512 mmol) in PhMe (10 mL) was heated at 70 °C under N2 for 20 min. A solution of Precursor 2 (325mg; 0.428 mmol) in PhMe (10 mL) was added and heated under reflux for 48-72 h, whilst stirring. The solution was cooled to room temperature and diluted with CH2CI2 (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2 x 20 mL), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n-hexane) to afford Compound 17 as a white solid (109 mg, 31 %).

The name for Compound 17 is 8-(4-bromobutyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno [1 ,2- djoxazole.

Compound 17 had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCh) 9.95 (1 H, s), 7.92 (1 H, s), 7.90 (1 H, s), 7.89 (1 H, s), 7.84 (1 H, s), 4.43 - 4.34 (4H, m), 4.30 - 4.24 (6H, m), 3.55 -

3.50 (2H, t, J 6.29 Hz), 3.15 - 3.10 (2H, t, J 7.05 Hz), 2.35 (3H, s), 2.25 - 1.94 (12H, m), 1.64 - 1.45 (24 H, m), 1.03 - 0.97 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 164.6, 149.6, 149.1 , 148.8, 148.4, 142.9, 140.1 , 139.7, 127.0, 124.7, 123.8, 123.5, 123.4, 116.3, 111.0, 108.4, 107.0, 102.7, 70.0, 69.9, 69.6, 69.6, 68.9, 33.0, 31.9, 29.3, 29.2, 29.2, 29.1 , 28.6, 28.5, 28.4, 28.3, 22.7, 25.3,

22.7, 22.6, 14.3, 14.2, 14.1 ppm. ES+ m/z: 834.4 ([M+H] + 95%), 836.4 ([M+H] + 100%).

Method of Synthesising Compound 18

Compound 18 was synthesised using the following method. A solution of Compound 17 (66 mg, 0.079 mmol) in acetone (10 ml_) was heated to 50 °C and stirred under N2, to this was added a solution of sodium azide (7 mg, 0.111 mmol) in H2O (5 ml_) and left stirring under IS for 4 h. After this time a precipitate had formed and the solvent was removed under reduced pressure, the precipitate was then filtered under vacumm and dried to give Compound 18 as an off white solid (59 mg, 94 %).

The name for Compound 18 is 8-(4-azidobutyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno [1 ,2- d]oxazole.

Compound 18 had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCI3) 9.96 (1 H, s), 7.94 (1 H, s), 7.90 (1 H, s), 7.90 (1 H, s), 7.87 (1 H, s), 4.45 - 4.40 (2H, t, J 6.70 Hz), 4.39 - 4.35 (2H, t, J 6.67 Hz), 4.30 - 4.24 (6H, m), 3.55 - 3.51 (2H, t, J 6.31 Hz), 3.17 - 3.12 (2H, t, J 7.11 Hz), 2.28 -

1.93 (12H, m), 1.65 - 1.41 (24H, m), 1.03 - 0.97 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDC ) 165.0,

149.6, 149.9, 149.4, 149.1, 148.7, 143.2, 140.4, 140.0, 127.3, 125.0, 124.1, 123.8, 123.7, 116.7, 111.3, 108.7, 107.3, 103.0, 70.3, 70.3, 69.9, 69.9, 69.2, 33.3, 32.3, 29.6, 29.5, 29.5, 29.4, 28.9,

28.8, 28.7, 28.6, 28.0, 25.6, 23.1 , 23.0, 14.6, 14.5, 14.5 ppm. ES+ m/z: 819.5 ([M+Na] + 100%).

Method of Synthesising Compound 19

Compound 19 was synthesised using the following method. Compound 17 (21 mg, 0.025 mmol) was dissolved in anhydrous THF (4 ml_) to this mixture potassium thioacetate (12 mg, 0.1 mmol) was added and stirred under N2 for 6 h. The organic phase was then extracted with DCM (10 mL) and washed with water (2 x 10 mL). The organic phase was then dried in vacuo and the solid recrystalised with DCM:MeOH (1 mL : 5 mL). The resultant precipitate was filtered under suction and the solid washed with methanol to give Compound 19 as an off white solid (4 mg, 19 %).

The name for Compound 19 is S-(4-(2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazol-8- yl)butyl) ethanethioate.

Compound 19 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCI3) 9.97 (1 H, s),

7.94 (1H, s), 7.90 (1 H, s), 7.89 (1 H, s), 7.86 (1H, s), 4.45 - 4.35 (4H, m), 4.30 - 4.24 (6H, m), 3.14 - 3.09 (2H, t, J 7.44 Hz), 3.02 - 2.97 (2H, t, J 7.21 Hz), 2.35 (3H, s), 2.18 - 1.80 (12H, m), 1.65 - 1.42 (24 H, m), 1.03 - 0.97 (15H, m) ppm. 13 C NMR 5c: (100 MHz, CDCb) 196.0, 165.2, 149.9, 149.4,

149.1, 148.7, 143.2, 140.4, 140.0, 127.2, 125.0, 124.2, 123.8, 123.6, 116.7, 111.4, 108.7, 107.3,

103.1, 70.3, 70.2, 69.9, 69.9, 69.2, 31.0, 30.1, 29.6, 29.5, 29.5, 29.4, 29.4, 29.1 , 28.9, 28.8, 28.7,

28.6, 28.5, 26.2, 23.0, 23.0, 14.6, 14.5, 14.5, 14.5 ppm. MALDI m/z: 829.5 ([M] + 100%).

Method of Synthesising Compound 20

Compound 22 was synthesised using the following method. A solution of Compound 17 (260 mg, 0.311 mmol), Sodium Tert-butoxide (90 mg, 0.934 mmol), Potassium Iodide (40 mg, 0.311 mmol) and Ethylene Glycol (193 mg, 3.11 mmol) in MeCN (15 mL) was heated to and held at reflux for 48 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The crude solid was dissolved with CH2CI2 (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2 x 20 mL) and then HCI (1M, 2 x 20 mL), separated and the organic phase was dried in vacuo. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 16 as a yellow solid (84 mg, 36 %).

The name for Compound 20 is 8-(but-3-en-1-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenylen o[1 ,2- d]oxazole.

Compound 20 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCb) 10.00 (1H, s), 7.92 (1H, s), 7.90 (1 H, s), 7.89 (1 H, s), 7.84 (1 H, s), 6.14 - 6.00 (1H, ddt, J 16.95, 10.20, 6.45 Hz), 5.22 (1H, dd, J 16.95, 1.60 Hz), 5.10 (1 H, dd, J 10.20, 1.60 Hz), 4.43 - 4.35 (4H, m), 4.30 - 4.24 (6H, m), 3.22 - 3.17 (2H, t, J 7.55 Hz), 3.17 - 3.12 (2H, t, J 7.11 Hz), 2.86 - 2.78 (2H, m), 2.08 - 1.94 (10H, m), 1.62 - 1.45 (20H, m), 1.03 - 0.97 (15H, m) ppm. 13 C NMR da: (100 MHz, CDCh) 165.0, 149.8,

149.4, 149.1 , 148.7, 143.2, 140.4, 140.0, 137.0, 127.2, 125.0, 124.2, 123.8, 123.6, 116.7, 116.3,

111.4, 108.7, 107.3, 107.2, 103.0, 70.3, 70.2, 69.9, 69.8, 69.2, 30.9, 29.6, 29.5, 29.4, 29.3, 28.9, 28.8, 28.7, 28.6, 28.5, 23.0, 22.9, 14.6, 14.5, 14.5 ppm. ES+ m/z: 754.5 ([M+H] + 100%).

Method of Synthesising Compound 21

Compound 21 was synthesised using the following method. A solution of decanoic acid (0.132 mg, 0.236 mmol), palladium diacetate (0.005 mmol) and iodobenzene didecanoate (0.235 mmol) in PhMe (10 mL) was heated at 70 °C under N2 for 20 min. A solution of Precursor 2 (100 mg; 0.132 mmol) in PhMe (10 mL) was added and heated under reflux for 48-72 h, whilst stirring. The solution was cooled to room temperature and diluted with CH2CI2 (20 mL). The organic phase was washed with aqueous NaOH (1M; 2 x 20 mL), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n-hexane) to afford Compound 21 as a white solid (42 mg, 39 %).

The name for Compound 21 is 8-nonyl-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole.

Compound 21 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 10.02 (1H, s), 7.93 (1 H, s), 7.90 (1 H, s), 7.89 (1 H, s), 7.84 (1 H, s), 4.43 - 4.36 (4H, m), 4.30 - 4.24 (6H, m), 3.11 - 3.06 (2H, t, J 7.52 Hz), 2.10 - 1.94 (12H, m), 1.63 - 1.29 (32H, m), 1.02 - 0.97 (15H, m) 0.91 - 0.87 (3H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 165.9, 149.8, 149.3, 149.0, 148.6, 143.2, 140.4, 140.1 ,

127.1, 124.9, 124.2, 123.8, 123.6, 123.6, 116.6, 111.3, 108.6, 107.2, 107.1 , 102.9, 70.2, 69.9, 69.8,

69.1, 32.3, 29.9, 29.8, 29.7, 29.6, 29.5, 29.4, 29.028.9, 28.8, 28.6, 27.1 23.1, 23.0, 14.6, 14.5 ppm. ES+ m/z: 826.6 ([M+H] + 100%).

Method of Synthesising Compound 22

Compound 22 was synthesised using the following method. A solution of Precursor 2 (100 mg, 0.132 mmol), 4-(dimethylamino)benzoyl chloride (175 mg, 0.658 mmol) and N,N-Diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 mins under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 22 as a yellow solid (19 mg, 18 %).

The name for Compound 22 is N,N-dimethyl-4-(2,3,6,11,12-pentakis(pentyloxy)triphenyleno[ 1 ,2- d]oxazol-8-yl)aniline.

Compound 22 had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCh) 10.20 (1 H, s), 8.27-8.24 (2H, d, J 8.60 Hz), 7.94 (1 H, s), 7.90 - 7.85 (3H, m), 6.89 - 6.86 (2H, d, J 8.60 Hz), 4.56 - 4.45 (4H, m), 4.31 - 4.24 (6H, m), 3.11 (6H, s), 2.16 - 1.94 (10H, m), 1.71 -1.42 (20H, m), 1.04 - 0.97 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 162.8, 152.2, 149.7, 149.3, 148.5, 143.1 , 141.4,

140.2, 129.3, 127.4, 124.9, 124.5, 124.0, 123.6, 116.5, 112.4, 111.5, 108.6, 107.3, 107.2, 103.4,

70.2, 70.2, 69.9, 69.2, 40.9, 29.6, 29.6, 29.5, 29.4, 29.0, 28.9, 28.8, 28.7, 23.0, 23.0, 14.7, 14.5 ppm. ES+ m/z: 819.7 ([M] + 100%).

Method of Synthesising Compound 23

Compound 23 was synthesised using the following method. A solution of 4-nitrobenzoic acid (1 g, 6 mmol), palladium diacetate (0.005 mmol) and (diacetoxyiodo)benzene (51 mg, 0.157 mmol) in PhMe (10 mL) was heated at 70 °C under N2 for 20 min. A solution of Precursor 2 (100 mg; 0.132 mmol) in PhMe (10 mL) was added and heated under reflux for 48-72 h, whilst stirring. The solution was cooled to room temperature and diluted with CH2CI2 (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2 x 20 mL), separated and the organic phase was dried in vacuo. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n-hexane) to afford Compound 23 as an off-white solid (74 mg, 69 %).

The name for Compound 23 is 8-(4-nitrophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenylen o[1 ,2- djoxazole. Compound 23 had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCh) 9.66 (1 H, s), 8.14 - 8.05 (4H, m), 7.74 (1H, s), 7.73 (1 H, s), 7.70 (1 H, s), 7.67 (1 H, s), 4.30 - 4.19 (10H, m), 2.04 - 1.94 (10H, m), 1.63 - 1.47 (20H, m), 1.05 - 1.00 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 158.9, 150.0, 149.3, 149.1, 148.8, 143.0, 140.6, 140.4, 132.8, 127.8, 127.5, 125.0, 124.0, 123.6,

123.5, 123.3, 116.5, 110.8, 108.3, 106.8, 106.4, 104.3, 70.2, 69.9, 69.8, 69.7, 69.1, 29.7, 29.6, 29.5,

29.4, 28.9, 28.8, 28.8, 28.7, 23.0, 14.6, 14.5 ppm. MALDI m/z: 820.5 ([M] + 100%).

Method of Synthesising Compound 24

Compound 24 was synthesised using the following method. A solution of (diacetoxyiodo)benzene (51 mg, 0.157 mmol) and acetylsalicylic acid (550 mg, 3.031 mmol) in toluene (4 ml_) was heated to 80 °C and stirred for 10 min under N2. Then Precursor 2 (100 mg, 0.131 mmol) was added to form a black solution which was then stirred for a further 10 mins. A solution of palladium diacetate (1 mg, 5 mol %) and acetylsalicyclic acid (553 mg, 3.197 mmol) in toluene (4 ml_) was heated to 110 °C and stirred for 10 mins under N2 before being combined with the black solution. The resultant solution was left stirring at 110 °C for 72 h under N2. The crude black solution was dried in vaccuo and purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n-hexane). The crude material was then evaporated to dryness in vacuo and then dissolved in a mixture of MeCN (10 mL) and 1 M NaOH (10 mL). The solution was heated to 80 °C for 2 h. After cooling to room temperature the product was acidified using 1 M HCI (20 mL) and extracted into CH2CI2 (3 x 10 mL). The combined organic layer was evaporated to dryness in vacuo to afford Compound 24 as a white solid (2 mg. 2 %).

The name for Compound 24 is 2-(2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazol-8- yl)phenol.

Compound 24 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 11.42 (1 H, s), 9.35 (1H, s), 8.20 - 8.17 (1H, dd, J 8.01, 1.67 Hz), 7.90 (1 H, s), 7.89 (1 H, s), 7.88 (1 H, s), 7.87 (1H, s), 7.52 - 7.46 (1H, ddd, J 8.51, 7.22, 1 .67 Hz), 7.18 - 7.14 (1H, dd, J 8.51, 1.08 Hz), 7.08 - 7.05 (1H, ddd, J 8.01, 7.22, 1.08 Hz), 4.47 - 4.42 (2H, t, J 6.65 Hz), 4.39 -4.35 (2H, t, J 6.71 Hz), 4.30 - 4.19 (6H, m), 2.09 - 1.94 (10H, m), 1.71 - 1.43 (20H, m), 1.05 -0.98 (15H, m) ppm. MALDI m/z: 791 ([M] + 100%).

Method of Synthesising Compound 25

Compound 25 was synthesised using the following method from Precursor 3.

Precursor 3 was fabricated according to the method described in N. Boden et. al. J. Mater. Chem., 1995, 5, 2275. A solution of 2,3,6,7,10,11-hexabutoxy-1-nitrotriphenylene (1.70 g, 2.79 mmol), sodium borohydride (1.70 g, 45.1. mmol) and nickel(ll) chloride hexahydrate (4.45 g, 18.7 mmol) in a 50/50 mix of MeOH and THF (40 mL) was stirred at room temperature for 5 h under N2. The crude black solid was then filtered and washed with CHCh and the filtrate evaporated to dryness in vacuo to afford Precursor 3 as a brown solid (1.6 g, 85 %).

The name for Precursor 3 is 2,3,6,7,10,11-hexabutoxytriphenylen-1-amine.

Precursor 3 had the following characterization data: 1 H NMR 5H: (300 MHz, CDCh) 8.82 (1 H, s), 7.83 (1 H, s), 7.80 (1 H, s), 7.78 (1 H, s), 7.37 (1 H, s), 4.57 (2 H, s), 4.29 - 4.09 (12 H, m), 2.01 - 1.81 (12 H, m), 1.67 - 1.52 (12 H, m), 1.13 - 0.94 (18 H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 151.0, 149.5, 148.9, 148.0, 147.6, 138.4, 135.6, 127.0, 124.7, 124.5, 124.1, 124.0, 114.0, 110.3,

108.5, 108.2, 107.1 , 97.4, 72.9, 69.7, 69.4, 69.1 , 68.4, 32.7, 31.8, 31.7, 31.6, 31.5, 19.7, 19.6, 19.5,

19.4, 14.1 ppm. MALDI m/z: 675.8 ([M] + 100%).

A solution of Precursor 3 (100 mg, 0.148 mmol), 2-napthoyl chloride (141 mg, 0.658 mmol) and N,N- diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 mins under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 25 as a yellow solid (21 mg, 19 %). The name for Compound 25 is 2,3,6,11 ,12-pentabutoxy-8-(naphthalen-2-yl)triphenyleno[1 ,2- d]oxazole.

Compound 25 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 10.01 (1 H, s), 8.68 (1H, s), 8.31 - 8.27 (1H, dd, J 8.57, 1.65 Hz), 7.96 - 7.87 (3H, m), 7.80 - 7.79 (3H, m), 7.70 (1H, s), 7.58 - 7.55 (2H, m), 4.45 - 4.40 (2H, t, J 7.01 Hz), 4.38 - 4.34 (2H, t, J 6.67 Hz), 4.28 - 4.19 (6H, m), 2.15 - 1.91 (10H, m), 1.79 - 1.59 (10H, m), 1.18 - 1.07 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 161.6, 149.7, 149.3, 149.0, 148.5, 143.1, 140.8, 140.4, 134.9, 133.4, 129.2, 128.3, 127.8, 127.3, 127.1 , 125.0, 124.9, 124.4, 124.1 , 123.7, 123.6, 116.6, 111.3, 108.4, 107.1, 106.9,

103.7, 69.8, 69.6, 69.5, 68.9, 31.9, 31.8, 19.9, 19.8, 19.7, 14.5, 14.4, 14.3 ppm. MALDI m/z: 755.1 ([M] + 100%).

Method of Synthesising Compound 26

Compound 26 was synthesised using the following method from Precursor 4 (2,3,6,7,10,11- hexakis(pentyloxy)-1,8-triphenylenediamine).

Precursor4 is synthesised using the method described in N. Boden et. al. J. Mater. Chem., 1995, 5, 2275 from the di-nitro triphenylene derivative, which is formed as a side product in the method that was used to synthesis the mono-nitro triphenylene derivative. The di-nitro triphenylene derivative may be isolated using flash column chromatography in an earlier fraction than the mono-nitro intermediate.

A solution of Precursor 4 (135 mg, 0.174 mmol) and palladium diacetate (0.0005 mmol) in PhMe (7 mL) was heated at reflux under N2for 10 min. 2-flourobenzoyl chloride (0.02 mL, 0.174 mmol) was added and heated under reflux for 40 h. The solution was cooled to room temperature and dried in vacuo and the resultant black solid was heated at 240 °C for 10 minutes before being cooled to room temperature. The crude black solid was purified by flash column chromatography (silica; 40 % CH2CI2: 60 % n-hexane) to afford Compound 26 as an off-white solid (6 mg, 4 %).

The name for Compound 26 is 2,9-bis(2-fluorophenyl)-4,7,12,13-tetrakis(pentyloxy)triphen yleno[1 ,2- d:8,7-d']bis(oxazole).

Compound 26 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 10.09 (2H, s), 8.38 - 8.32 (2H, td, J 7.56, 7.52, 1.78 Hz), 7.82 (2H, m), 7.58 (2H, m), 7.36 - 7.31 (2H, m), 7.29 - 7.25 (2H, m), 4.48 - 4.39 (8H, m), 2.16 - 1.96 (8H, m), 1.70 - 1.44 (16H, m), 1.05 - 1.00 (12H, m) ppm. 19 F NMR dr: (300 MHz, CDCh) 108.9 (s) ppm. MALDI m/z: 842.5 ([M] + 100%).

Method of Synthesising Compound 27

Compound 27 was synthesised using the following method. A solution of 4'-Carboxybenzo-15- crown-5 (600 mg, 1.92 mmol), Oxalyl chloride (2.0 mL, 23.6 mmol) and Dimethylformamide (0.01 ml, 0.129 mmol) was heated and held at reflux for 10 minutes under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. A solution of Precursor 2 (100 mg, 0.132 mmol) and N,N-Diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was added. The reaction was then heated and held at reflux for 72 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 mins under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 10 % EtOAc: 90 % n-hexane) to afford compound 27 as a brown solid (22 mg, 17 %).

The name for Compound 27 is 8-(2,3,5,6,8,9, 11,12- octahydrobenzo[b][1 ,4,7,10,13]pentaoxacyclopentadecin-15-yl)-2,3,6,11,12- pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole.

Compound 27 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 10.10 (1 H, s), 8.04 - 7.80 (6 H, m), 6.99 (1 H, d, J 8.35 Hz), 4.53 - 4.38 (4H, m), 4.33 - 4.17 (10H, m), 4.06 - 3.90 (4H, m), 3.89 - 3.73 (8H, m), 2.10 - 1.88 (10H, m), 1.69 - 1.44 (20H, m), 1.07 0.92 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 161.6, 152.1 , 149.6, 149.1 , 148.9, 148.4, 142.9, 140.7, 140.1 , 127.2,

124.7, 124.0, 123.6, 123.4, 121.7, 120.5, 116.4, 113.2, 112.9, 111.1, 108.3, 107.0, 103.4, 71.3, 70.6, 70.5, 70.0, 70.0, 69.9, 69.6, 69.5, 69.2, 68.9, 68.7, 29.8, 29.4, 29.3, 29.2, 28.7, 28.5, 28.4, 22.8, 22.7, 14.4, 14.3 ppm. MALDI m/z: 965.9 ([M] + 100%).

Method of Synthesising Compound 28

Compound 28 was synthesised using the following method. A solution of Compound 2 (60 mg, 0.077 mmol) in degassed dichloromethane (5 ml_) was stirred in a nitrogen purged 2 neck flask under nitrogen atmosphere at -20 °C. Boron tribromide (1 M solution in CH2CI2, 387 pl_, 0.385 mmol, 5 eq) was added via syringe through a Suba-Seal(RTM) and the dark yellow solution was stirred for at room temperature for 24 h. Water (40 ml_) was added to quench the reaction and the product was extracted with dichloromethane (10 rriL), washed with water (2 * 20 rriL) and dried over MgS0 4 . The organic phase was evaporated to dryness and purified by column chromatography (Silica: 5% Ethyl acetate : Hexane) to afford Compound 28 as a brown solid (10 mg, 6 %).

The name for Compound 28 is 2,3,11,12-tetrakis(pentyloxy)-8-phenyltriphenyleno[1 ,2-d]oxazol-6-ol.

Compound 28 had the following characterisation data: 1 H NMR (300 MHz, CDCI3) 6H: 10.09 (1 H, s), 8.48 (2H, dd, J 6.86, 2.85 Hz), 7.94 (1 H, s), 7.90 (1 H, s), 7.88 (1 H, s), 7.83 (1H, s), 7.59 - 7.56 (3H, m), 5.95 (1 H, s br), 4.48 (2H, t, J 6.60 Hz), 4.33 (2H, t, J 6.51 Hz), 4.26 - 4.24 (4H, m), 2.06 - 1.93 (8H, m), 1.64 - 1.43 (16H, m), 1.01 - 0.97 (12H, m) ppm. ES + MS m/z: 728.4 ([M+Na] + 25 %), 707.4 ([M+H+1G 30 %), 706.4 ([M+H] + 85 %).

Method of Synthesising Compound 29

Compound 29 was synthesised using the following method. Compound 2 (250 mg, 0.322 mmol) was dissolved in dry CH2CI2 (10 ml_) and stirred at 0 °C under a N2 atmosphere. 0.01 M solution of Br2 in CH2CI2 (144 mL, 1.449 mmol) was then added over 2 h (4 * 36 mL) and monitered by TLC. The reaction was quenched by addition of saturated sodium metabisulfate solution (100 mL). The product was extracted with dichloromethane (30 mL) washed with water (3 * 30 mL), dried over MgS04 and evaporated to dryness. The crude product was then purified by column chromatography (Silica 40 % CH2CI2: n-hexane) to yield Compound 29 as a yellow solid (170 mg, 62 %).

The name for Compound 29 is 1-bromo-2,3,6,11,12-pentakis(pentyloxy)-8-phenyltriphenyleno [1,2- djoxazole.

Compound 29 had the following characterisation data: 1 H NMR (300 MHz, CDCI3) 6H: 10.06 (1 H, s), 8.71 (1 H, s), 8.56 (1 H, s), 8.34 - 8.31 (2H, m), 7.60 - 7.58 (4H, m), 4.59 (2H, t, J 6.5 Hz), 4.41 (2H, t, J 6.8 Hz), 4.26 - 4.20 (6H, m), 2.06 - 1.90 (10H, m), 1.64 - 1.42 (20H, m), 1.02 - 0.94 (15H, m) ppm.

Method of Synthesising Compound 30

Compound 30 was synthesised using the following method. Compound 29 (170 mg, 0.199 mmol), K2CO3 (410 mg, 2.97 mmol) and Pd(PPh3)4 (30 mg, 0.026 mmol) were dissolved in degassed 5 : 1 THF:H2<D mix (4 mL) under nitrogen atmosphere. (4-hydroxyphenyl)boronic acid (140 mg, 1.02 mmol) was then added and the reaction was heated to reflux under N2 for 24 h. The product was extracted with dichloromethane (30 mL), washed with water (3 * 30 mL) and evaporated to dryness. The crude product was purified by column chromatography (Silica CH2CI2: n-hexane) to yield impure Compound 30 as a brown solid.

The name for Compound 30 is 4-(2,3,6,11,12-pentakis(pentyloxy)-8-phenyltriphenyleno[1 ,2- d]oxazol-1-yl)phenol.

Compound 30 had the following characterisation data: TOF LD + m/z: 869.49 ([M+1] + 70 %), 868.52 ([M] + 70 %).

Method of Synthesising Compound 31

Compound 31 was synthesised using the following method. Compound 10 (50.7 mg, 0.071 mmol) was added to a 2 neck round bottom flask, which was purged with N2 for 15 min. Dry CH2CI2 (20 mL) was then added via syringe through a Suba-Seal(RTM) and the brown stirring solution was cooled to -78 °C. Boron tribromide (1 M solution in CH2CI2, 391 pL, 0.391 mmol, 5.5 eq) was added via syringe through a Suba-Seal(RTM) and the reaction was stirred for 4 h. The reaction mixture was poured over crushed ice and stirred until the ice had fully melted, 4 drops of hydrochloric acid (1M) were added and the product was extracted with ethyl acetate, washed with water (2 * 20 mL), and dried over MgS04 and evaporated to dryness. The crude product was used without further purification.

The name for Compound 31 is 8-methyltriphenyleno[1,2-d]oxazole-2,3,6,11 ,12-pentaol.

Compound 31 had the following characterisation data: ES + MS m/z: 503.26 ([M+2(OCsHn)] + 50 %), 433.17 ([M+( OCsHii)] + 100 %), 363.08 ([M] + 10 %).

Method of Synthesising Compound 32

Crude Compound 31 (26 mg, 0.071 mmol), potassium carbonate (74 mg, 0.533 mmol), potassium iodide (6 mg, 0.036 mmol) was dissolved in dry MeCN (35 mL). 1 (-2-Bromoethoxy)-2-(2- methoxyethoxy)ethane (132 pL, 0.533 mmol) was then added via pipette and the reaction was heated to reflux and stirred under a CaCh drying tube for 20 h. The reaction was cooled to room temperature and the product was extracted with ethyl acetate (20 mL), washed with water (3 c 20 mL), brine (2 c 20 mL) and dried over MgS04 to yield crude Compound 32 as a brown solid.

The name for Compound 32 is 2,3,6, 12-tetrakis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-8-methyl-11 - (pentyloxy)triphenyleno[1 ,2-d]oxazole.

Compound 32 had the following characterisation data: ES + MS m/z: 1017.5 ([M] + 100 %). Advantageously, Compound 32 is water soluble.

Method of Synthesising Compound 33

Compound 33 was synthesised from Precursor 5 in the following method. The starting material to form Precursor 5 was obtained using the method described in J. Mater. Chem. C, 2017,5, 669- 682 (DOI: 10.1039/C6TC04530H).

5,6-Dimethoxy-2,3,8,9,12,13-hexakis(pentyloxy)dibenzo[fg, op]tetracene (681mg, 0.775 mmol) was dissolved in diethyl ether (20 ml) and then acetic acid (1.33 ml, 23.24 mmol, 30 eqiv) was added and the mixture stirred at room temperature in a nitrogen atmosphere for 10 minutes before the addition of fuming nitric acid (65 pL, 1.55 mmol, 2 equiv) was added. The reaction mixture was stirred under nitrogen for 20 min before the further addition of nitric acid (30 pL, 0.715 mmol, 0.92 eq) and the reaction mixture was left for 20 min stirring at room temperature. The mixture was then quenched with water (10 ml) and the organic phase was washed with NaOH (1 M, 2 x 30 mL) and then dried in vacuo to provide Precursor 5 as a black solid (680 mg, 95 %). This was used in the next step with no further purification.

The name for Precursor 5 is 5,6-dimethoxy-1-nitro-2,3,8,9,12,13- hexakis(pentyloxy)dibenzo[fg,op]tetracene.

Precursor 5 had the following characterisation data: 1 H NMR (400 MHz, CDCh) 6H 9.16 (1H, s), 9.01 (1H, s), 7.95 (1 H, s), 7.84 (1 H, s), 7.58 (1H, s), 4.53 (2H, t, J 6.7 Hz), 4.32 (2H, t, J 5.1 Hz), 4.29 (2H, t, J 5.3 Hz), 4.18 - 4.14 (2H, m), 4.14 (3H, s), 4.13 (3H, s), 3.95 (2H, t, J 6.8 Hz), 3.95 (2H, t, J 7.0 Hz), 2.11 - 1.82 (12H, m), 1.69 - 1.29 (24H, m), 1.08 - 0.84 (18H, m). 13 C NMR (101 MHz, CDCh) da 151.9, 149.6, 149.3, 148.7, 148.1, 147.9, 144.4, 143.2, 141.5, 124.9, 124.8, 124.7, 124.4, 123.1, 123.1, 122.3, 119.4, 118.6, 116.0, 109.5, 109.3, 107.6, 107.3, 104.9, 76.3, 74.5, 74.0, 69.5, 68.9, 68.8, 55.8, 30.3, 30.3, 29.9, 29.2, 29.0, 28.8, 28.4, 28.3, 28.2, 28.1, 22.6, 22.6, 22.6, 14.1 , 14.0, 14.0. MALDT m/z: 924.82 ([M+H] + 30 %).

Precursor 6 was synthesised in the following method. Precursor 5 (680 mg, 0.736 mmol) and NiCh.6H20 (552 mg, 2.33 mmol, 3 equivalents) were dissolved in THF:MeOH (20 mL, 5:4 ratio), to make a yellow solution, and then NaBH4 (586 mg, 15.5 mmol, 20 equivalents) was added over 15 minutes. The black reaction mixture was left stirring under a N2 atmosphere for 40 min after which time it was diluted with chloroform and the precipitate was gravity filters to leave a brown organic phase, which was then dried in vacuo to provide Precursor 6 as brown solid (614 mg, 93 %).

The name for Precursor 6 is 5,6-dimethoxy-2,3,8,9,12,13-hexakis(pentyloxy)dibenzo[fg,op] tetracen- 1-amine.

Precursor 6 had the following characterisation data: 1 H NMR (300 MHz, CDCI3) 6H 9.09 (1H, s), 8.98 (1H, s), 8.67 (1 H, s), 7.97 (1 H, s), 7.90 (1 H, s), 4.76 (2H, s), 4.40 (2H, t, J 6.8 Hz), 4.34 (2H, t, J 6.5 Hz), 4.28 (2H, t, J 6.6 Hz), 4.20 (2H, t, J 6.6 Hz), 4.11 (3H, s), 4.08 (3H, s), 3.99 (2H, t, J 7.0 Hz), 3.93 (2H, t, J 7.0 Hz), 2.07 - 1.88 (12H, m), 1.66 - 1.34 (24H, m), 1 .06 - 0.88 (18H, m, J 22.0, 12.0, 7.1 Hz). 13 C NMR (101 MHz, CDCb) 6c 151.2, 148.5, 148.2, 148.0, 146.8, 143.8, 139.8, 136.9, 125.4, 125.0, 124.5, 124.4, 123.6, 123.5, 122.6, 120.5, 113.9, 111.8, 110.0, 109.4, 108.6, 108.4, 104.3, 73.9, 73.8, 69.7, 69.2, 69.0, 55.7, 30.4, 30.3, 29.7, 29.3, 29.1 , 29.0, 28.5, 28.4, 28.3, 22.7, 22.6, 22.6, 14.1 , 14.0. MALDT m/z: 893.8 ([M+H] + 100%).

Precursor 7 was synthesised in the following method. Precursor 6 (147 mg, 0.181 mmol) was dissolved in dry CH2CI2 (20 ml_) and dry MeCN (20 ml_). The solution was cooled to 0 °C under a N2 atmosphere then ferf-butyl nitrite (34 pL, 0.309 mmol, 1.7 equivalents) and TMSN3 (36 pL, 0.273 mmol, 1.5 equivalents) were added and the reaction mixture stirred 0 °C for 10 min and then at room temperature for 20 min. The solution was then dried in vacuo and purified via flash column chromatography (silica, 30 % DCM, 70 % n-hexane) to provide Precursor 7 as a while solid (120 mg, 72 %).

The name for Precursor 7 is 1-azido-5,6-dimethoxy-2,3,8,9,12,13- hexakis(pentyloxy)dibenzo[fg,op]tetracene.

Precursor 7 had the following characterisation data: 1 H NMR (300 MHz, CDCb) 6H 9.12 (1H, s), 9.03 (1 H, s), 8.98 (1 H, s), 8.01 (1 H, s), 7.89 (1 H, s), 4.45 (2H, t, J 6.7 Hz), 4.38 - 4.32 (2H, m), 4.29 (2H, t, J = 6.0 Hz), 4.11 (3H, s), 4.09 (3H, s), 4.01 (2H, m), 3.94 (2H, t, J 6.6 Hz), 2.13 - 1.84 (12H, m,), 1.69 - 1.32 (24 H, m), 1.04 - 0.87 (18H, m). 13 C NMR (101 MHz, CDCb) 6c 151.6, 148.9, 148.0, 148.0, 147.9, 147.9, 146.3, 144.1 , 127.3, 125.4, 124.8, 124.0, 123.9, 123.3, 123.2, 122.8, 120.2, 119.4, 117.6, 112.6, 109.4, 109.1 , 107.5, 104.7, 75.3, 74.4, 74.0, 69.6, 69.1 , 69.0, 55.8, 30.4, 30.3, 29.5, 29.3, 29.1 , 28.9, 28.5, 28.3, 28.2, 28.1, 22.7, 22.6, 22.5, 14.1, 14.0.

Compound 33 was synthesised using the following method. Precursor 7 (100 mg; 0.13 mmol) was dissolved in dry PhMe (5 mL) was added to a flask containing rhodium octanoate dimer (5 mg; 0.01 mmol), under a N2 atmosphere. This mixture was then heated to reflux and stirred for 20 hours. The reaction was cooled to room temperature and then dried in vacuo, the solid was then purified via flash column chromatography (silica; 95 % n-hexane: 5 % ethyl acetate) to provide Compound 33 as a white solid (58 mg, 50 %).

The name of Compound 33 is 2-butyl-12,13-dimethoxy-5,6,9,10,15- pentakis(pentyloxy)dibenzo[4,5:9,10]pyreno[1 ,2-d]oxazole.

Compound 33 had the following characterisation data: 1 H NMR (300 MHz, CDCb) 6H 10.08 (1H, s), 9.28 (1H, s), 9.15 (1 H, s), 8.16 (1 H, s), 8.02 (1H, s), 4.42 (2H, t, J 6.0 Hz), 4.37 (2H, d, J = 5.8 Hz), 4.35 - 4.29 (4H, m, J 6.7, 3.3 Hz), 4.12 (3H, s), 4.11 (3H, s), 3.98 (2H, t, J = 6.9 Hz), 3.18 (2H, t, J = 7.5 Hz), 2.09 - 1.92 (10H, m), 1.67 - 1.36 (24H, m), 1.07 - 0.90 (18H, m). 13 C NMR (101 MHz, CDCb) 6c 166.1, 151.3, 149.5, 148.8, 147.8, 147.7, 144.0, 142.4, 138.4, 137.1 , 125.5, 124.9, 124.1 , 124.0, 123.7, 123.5, 123.0, 119.9, 118.8, 116.1, 111.3, 109.6, 109.4, 107.1 , 104.8, 74.5, 74.0, 69.8, 69.0, 68.8, 55.8, 55.7, 30.3, 30.1, 29.3, 29.1 , 28.9, 28.7, 28.5, 28.4, 28.3, 28.2, 22.6, 22.5, 22.3, 14.1, 14.0, 13.8. MALD G m/z: 889.2 ([M+H] + 100%).

Method of Synthesising Compound 34

Precursor 6 (47 mg; 0.053 mmol), benzoyl chloride (30 pL, 0.265 mmol, 5 equivalents), and diisopropylethylamine (46 pL, 0.265 mmol, 5 equiv) were dissolved in dry PhMe (5 mL) and the mixture was heated to reflux under a N2 atmosphere. The reaction mixture was stirred for 1 h at which point the mixture was dried in vacuo then the solid was heated to 240 °C for 10 min. The reaction was cooled to room temperature and the solid was then purified via flash column chromatography (silica; 40 % CH2CI2, 60 % n-hexane) to afford Compound 34 a white solid (16 mg, 33 %).

The name of Compound 34 is12,13-dimethoxy-5,6,9,10,15-pentakis(pentyloxy)-2- phenyldibenzo[4,5:9,10]pyreno[1 ,2-d]oxazole.

Compound 34 had the following characterisation data: 1 H NMR (300 MHz, CDCh) 5H 9.29 (1 H, s), 9.19 (1H, s), 8.48 - 8.43 (2H, m), 8.17 (1 H, s), 8.03 (1 H, s), 7.65 - 7.59 (3H, m), 4.53 (2H, t, J = 6.9 Hz), 4.44 - 4.33 (6H, m), 4.14 (3H, s), 4.12 (3H, s), 3.99 (2H, t, J = 6.9 Hz), 2.15 - 1.90 (10H, m),

1.71 - 1.36 (24 H, m), 1.06 - 0.80 (18H, m). 13 C NMR (101 MHz, CDCh) 6c 166.6, 161.8, 151.4,

149.5, 148.9, 147.9, 147.9, 144.1 , 142.5, 138.5, 137.7, 132.9, 131.5, 129.5, 129.0, 128.4, 127.6,

127.4, 125.6, 124.8, 124.3, 124.0, 123.8, 123.5, 123.3, 119.8, 119.7, 116.4, 111.3, 109.7, 109.4,

106.9, 104.8, 74.7, 74.1, 69.8, 69.0, 64.5, 55.8, 55.7, 30.4, 30.2, 29.7, 29.3, 29.1, 28.9, 28.5, 28.5,

28.4, 25.6, 22.6, 22.5, 14.2, 14.1 , 14.1 , 14.1, 14.0. ES + m/z: 910.5 ([M+H] + 100%).

Method of Synthesising Compound 35

Precursor 6 (100 mg; 0.111 mmol) 4-cyanobenzoyl chloride (92 mg, 0.555 mmol, 5 equiv), and diisopropylethylamine (90 pl_, 0.555 mmol, 5 equiv) were dissolved in dry toluene (5 mL) and the mixture was heated reflux under a nitrogen atmosphere. The reaction mixture was stirred for 1 hour at which point the mixture was dried in vaccuo then the solid was heated to 240 °C for 10 minutes. The reaction was cooled to room temperature and the solid was then purified via flash column chromatography (silica; 40 % DCM, 60 % n-hexane) to afford Compound 35 as a white solid (17 mg, 16 %).

The name of Compound 35 is 4-(12,13-dimethoxy-5,6,9,10,15- pentakis(pentyloxy)dibenzo[4,5:9,10]pyreno[1 ,2-d]oxazol-2-yl)benzonitrile.

Compound 35 had the following characterisation data: 1 H NMR (300 MHz, CDCh) d 10.02 (s, 1 H), 9.27 (s, 1 H), 9.15 (s, 1 H), 8.43 (d, J = 8.3 Hz, 2H), 8.13 (s, 1 H), 7.99 (s, 1 H), 7.84 (d, J = 8.3 Hz, 2H), 4.45 (t, J = 6.8 Hz, 2H), 4.36 (dt, J = 13.0, 6.4 Hz, 6H), 4.14 (s, 3H), 4.12 (s, 3H), 3.97 (t, J = 6.9 Hz, 2H), 2.12 - 1.90 (m, 10H), 1.65 - 1.38 (m, 24H), 1.06 - 0.88 (m, 18H). 13 C NMR (100 MHz, CDCh) d 159.8, 151.9, 149.9, 149.5, 148.5, 148.3, 144.6, 143.0, 138.6, 137.6, 133.0, 131.5, 128.0, 125.8, 124.8, 124.4, 123.9, 123.8, 123.8, 121.1 , 119.9, 118.6, 117.0, 114.7, 111.5, 110.1, 109.8, 107.1, 105.2, 75.1 , 74.4, 70.1 , 69.3, 56.2, 56.1 , 30.7, 30.5, 30.0, 29.6, 29.5, 29.3, 28.9, 28.8, 28.7,

28.7, 23.0, 22.9, 22.9, 14.6, 14.5, 14.4. MALDT m/z: 934.55 ([M+H] + 100%).

Method of Synthesising Compound 36

Compound 1 was synthesised using the following method. A solution of Precursor 1 (100 mg, 0.132 mmol), benzoyl chloride (92 mg, 0.658 mmol) and N,N-diisopropylethylamine (0.1 mil, 0.574 mmol) in PhMe (5 mil) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo purified via flash column chromatography (silica, 60 % CH2CI2: 40 % n- hexane) to afford an intermediate as a brown solid (19 mg, 18 %).

The intermediate had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCh) 8.55 (1 H, s), 8.45 (1 H, s), 8.07 (2H, d, J 7.5 Hz), 7.78 (1 H, s), 7.74 (1 H, s), 7.72 (1 H, s), 7.71 (1 H, s), 7.59 (1 H, d, J 7.0 Hz), 7.54 (2H, t, J 7.4 Hz), 4.28 - 4.12 (10H, m), 3.67 - 3.54 (2H, m), 2.00 - 1.85 (8H, m), 1.70 - 1.37 (20H, m), 1 .34 - 1.06 (8H, m), 1.02 - 0.90 (12H, m), 0.83 (3H, t, J 7.0), 0.75 (3H, t, J 7.1) ppm. 13 C NMR 6c: (100 MHz, CDCh) 174.6, 151.0, 149.7, 148.7, 148.4, 148.4, 144.0, 135.1 ,

131.7, 130.9, 128.5, 127.9, 126.6, 124.7, 124.2, 123.0, 122.6, 122.0, 110.3, 108.1 , 107.7, 106.8,

106.7, 73.4, 70.1 , 70.0, 69.5, 69.3, 68.8, 32.1 , 30.1 , 29.9, 29.6, 29.4, 29.3, 28.7, 28.5, 28.5, 28.1 ,

22.9, 22.7, 22.6, 14.3, 14.3, 14.1 ppm. MALDI m/z: 863.3 ([M]+ 100%).

A solution of the intermediate (100 mg, 0.116 mmol) and Lawesson’s Reagent (175 mg, 0.658 mmol) in PhMe (5 mL) was heated to and held at reflux for 48 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 min under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 36 as a green solid (17 mg, 19 %).

The name for Compound 36 is 2,3,6,11 ,12-pentakis(pentyloxy)-8-phenyltriphenyleno[1 ,2-d]thiazole.

Compound 36 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCI3) 10.51 (1 H, s), 8.24-8.22 (2H, m), 7.92-7.89 (3H, m), 7.76 (1 H, s), 7.53-7.52 (3H, m), 4.43 - 4.26 (10H, m), 2.10 - 1.95 (10H, m), 1.66-1.57 (10H, m), 1.53 - 1.47 (10H, m), 1.03 - 1.00 (15H, m) ppm. 13 C NMR 5c: (100 MHz, CDC ) 166.4, 152.5, 151.5, 150.2, 149.3, 148.3, 134.7, 130.9, 130.0, 129.3, 127.6, 125.7, 125.4, 124.7, 123.8, 119.0, 112.4, 108.9, 107.2, 106.9, 100.9, 70.3, 70.2, 69.7, 69.2, 69.1, 29.7, 29.6, 29.6, 29.5, 29.4, 28.8, 28.8, 28.8, 23.1 , 23.0, 23.0, 23.0 23.0, 14.5, 14.5, 14.5, 14.5 ppm. MALDI m/z: 791.6 ([M]+ 100%).

Method of Synthesising Compound 37

Compound 37 was synthesised using the following method. A solution of Precursor 1 (100 mg, 0.132 mmol), 4-cyanobenzoyl chloride (109 mg, 0.658 mmol) and N,N-diisopropylethylamine (0.1 ml_, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The crude brown solid was added to a solution of Lawesson’s Reagent (175 mg, 0.658 mmol) in PhMe (5 mL) was heated to and held at reflux for 48 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 min under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 37 as a yellow solid (5 mg, 5 %).

The name for Compound 37 is 4-(2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]thiazol-8- yl)benzonitrile.

Compound 37 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCI3) 10.38 (1 H, s), 8.31 (2H, d, J 8.4), 7.97-7.88 (4H, m), 7.79 (1 H, d, J 8.5), 4.41-4.26 (10H, m), 2.06-1.95 (10H, m), 1.61-1.55 (10H, m), 1.51-1.44 (10H, m), 1.03-0.97 (15H, m) ppm. MALDI m/z: 816.9 ([M]+ 90%), 817.9 ([M+H] + 100%).

Method of Synthesising Compound 38

Compound 38 was synthesised from Precursor 8 in the following method.

Precursor 8 was synthesised using the following method. Compound 3 (8-(naphthalen-2-yl)- 2,3,6,11 ,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole) (150 mg, 0.18 mmol, 1 eq) was dissolved in CH2CI2 (10 mL) which had been dried and degassed for 10 min in a 2 necked flask fitted with a Subaseal(RTM) and had been purged with N2 for 10 min. The green solution was stirred at - 10° C under N2 for 10 min and boron tribromide (1 M in CH2CI2 solution) (0.2 mmol, 1.1 eq) was added via syringe through the Subaseal(RTM). The black solution was stirred under N2 for 2 h at - 10° C and then poured over crushed ice and stirred until all the ice had melted. The product was then extracted with ethyl acetate (20 mL), washed with water (3 * 50 mL) and evaporated to dryness yielding a brown solid. The product was then purified by flash column chromatography (20 % EtOAc: n- hexane, silica) yielding 8-(naphthalen-2-yl)-2, 3,6,12-tetrakis(pentyloxy)triphenyleno[1 ,2-d]oxazol- 11-ol as a yellow solid (31 mg, 23 %).

The name for Precursor 8 is 8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno [1 ,2- d]oxazol-11-ol.

Precursor 8 had the following characterisation data 1 H NMR 5H: (300 MHz, CDCI3) 10.06 (1 H, s),

8.83 (1H, s), 8.50 (1 H, dd, J 8.6, 1.7), 8.05 - 8.03 (1H, m), 7.79 (1 H, d, J 8.7), 7.91 - 7.89 (1 H, m),

7.84 (1 H, s), 7.79 (1 H, s), 7.78 (1 H, s), 7.74 (1 H, s), 7.58 - 7.56 (2H, m), 5.97 (1 H, s), 4.42 (2H, t, J 6.7), 4.29 - 4.20 (6H, m), 2.05 - 1.93 (8H, m), 1.63 - 1.45 (16H, m), 1.05 - 0.98 (12H, m) ppm. 13 C NMR 6c: (100 MHz, CDCb) 161.7, 149.4, 148.9, 146.0, 145.3, 143.0, 140.9, 140.2, 134.8, 133.2, 129.1, 128.66, 128.0, 127.9, 127.6, 127.2, 126.8, 124.8, 124.7, 124.7, 124.0, 123.6, 123.4, 116.4, 112.7, 108.1 , 107.1 , 103.7, 103.6, 69.9, 69.8, 69.7, 69.1 , 29.3, 29.3, 29.2, 28.6, 28.5, 28.4, 22.8, 22.7, 14.3, 14.2 ppm. MALDI m/z: 755.65 ([M] + 100%), 756.66 ([M+H] + 70%), 757.67 ([M+1+H] + 25%).

A slurry of Precursor 8 (100 mg, 0.13 mmol) and K2CO3 (114 mg, 0.83 mmol) in DMF (5 ml_) was heated at reflux with a CaC drying tube for 0.5 h, followed by addition of methyl 2-(2-(2- chloroethoxy)ethoxy)acetate (114 mg, 0.40 mmol) and Kl (75 mg, 0.5 mmol). The resultant slurry was further heated at reflux for 3 h. The reaction mixture was allowed to cool to room temperature and the precipitate filtered off via suction filtration. The solvent was evaporated from the filtrate to dryness in vacuo and the crude solid was purified by purified via flash column chromatography (silica, 25 % EtOAc: 75 % n- hexane) to afford Compound 38 as a yellow solid (36 mg, 30 %).

The name for Compound 38 is methyl 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12- tetrakis(pentyloxy)triphenyleno[1 ,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)acetate.

Compound 38 had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCI3) 10.16 (1 H, s), 8.83 (1 H, s), 8.50 (1 H, dd, J 8.6, 1.7), 8.05 - 8.03 (2H, m), 7.91 - 7.81 (5H, m), 7.58 - 7.56 (2H, m), 4.60 (2H, t, J 5.5), 4.42 (2H, t, J 6.7), 4.29 - 4.21 (6H, m), 4.20 (3H, s), 3.85-3.65 (8H, m), 2.05 - 1.93 (8H, m), 1 .63 - 1.45 (16H, m), 1.05 - 0.98 (12H, m) ppm. 13 C NMR 6c: (100 MHz, CDC ) 173.9,

161.7, 149.4, 148.9, 145.9, 145.3, 142.0, 140.8, 140.4, 134.8, 133.1 , 129.1, 128.7, 128.0, 127.9,

127.6, 127.2, 126.8, 124.8, 124.7, 124.6, 124.0, 123.6, 123.3, 116.5, 112.7, 108.1, 107.1, 103.7,

103.6, 71.8, 71.4, 71.2, 70.4, 69.8, 69.8, 69.7, 69.0, 68.5, 29.4, 29.3, 29.2, 28.6, 28.5, 28.4, 22.8,

22.7, 14.3, 14.2 ppm. MALDI m/z: 915.7 ([M]Ί00 %), 916.7 ([M+H] + 90 %). Elemental analysis Found: C, 73.41 ; H, 7.56; N, 1.54 %. C 56 H69NOIO requires C, 73.42; H, 7.59; N, 1.53 %.

Method of Synthesising Compound 39

Compound 39 was synthesised using the following method. A solution of NaOH (3 mg, 0.08 mmol) in H2O (1 mL) was added to a solution of Compound 38 (35 mg, 0.04 mmol in MeOH (5 mL). The resultant solution was heated at reflux for 5 h. The reaction mixture was allowed to cool to room temperature and aliquots of 1 M HCI aqueous solution was added until no further precipitate was formed. The precipitate was collected through suction filtration affording a yellow solid (24 mg, 70 %).

The name for Compound 39 is 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12- tetrakis(pentyloxy)triphenyleno[1 ,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)acetic acid.

Compound 39 had the following characterisation data: 1 H NMR 5H: (300 MHz, CDCI3) 10.16 (1 H, s), 8.83 (1 H, s), 8.50 (1 H, dd, J 8.6, 1.6), 8.05 - 8.03 (2H, m), 7.91 - 7.81 (5H, m), 7.58 - 7.56 (2H, m), 4.60 (2H, t, J 5.5 Hz), 4.42 (2H, t, J 6.7 Hz), 4.29 - 4.21 (6H, m), 3.85-3.65 (8H, m), 2.05 - 1.93 (8H, m), 1.63 - 1.45 (16H, m), 1.05 - 0.98 (12H, m) ppm. 13 C NMR 5c: (100 MHz, CDCI3) 175.7, 149.4, 148.9, 145.9, 145.3, 142.0, 140.8, 140.4, 134.8, 133.1 , 129.1 , 128.7, 128.0, 127.9, 127.6, 127.2, 126.8, 124.8, 124.7, 124.6, 124.0, 123.6, 123.3, 116.5, 112.7, 108.1 , 107.1 , 103.7, 103.6, 71.8, 71.4, 71.2, 70.4, 69.8, 69.8, 69.7, 69.0, 68.5, 29.4, 29.3, 29.2, 28.6, 28.5, 28.4, 22.8, 22.7, 14.3, 14.2 ppm. MALDI m/z: 901.5 ([M] + 100%), 902.5 ([M+H] + 70%). Elemental analysis Found: C, 73.24; H, 7.52;

N, 1.54 %. C55H67NO10 requires C, 73.23; H, 7.55; N, 1.55 %.

Method of Synthesising Compound 40

Compound 40 was synthesised using the following method. A slurry of Precursor 8 (100 mg, 0.13 mmol) and K2CO3 (37 mg, 0.26 mmol) in MeCN (5 mL) was heated at reflux with a CaCh drying tube for 0.5 h, followed by addition of 2-(2-(2-azidoethoxy)ethoxy)ethyl 4-methyl benzenesulfonate (87 mg,

O.26 mmol). The resultant slurry was further heated at reflux for 24 h. The reaction mixture was allowed to cool to room temperature and the precipitate filtered off via suction filtration. The solvent was evaporated from the filtrate to dryness in vacuo and the crude solid was purified by purified via flash column chromatography (silica, 25 % EtOAc: 75 % n- hexane) to afford Compound 38 as a yellow solid (18 mg, 15 %).

The name for Compound 40 is 11-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)-8-(naphthalen-2-yl)-2 ,3,6,12- tetrakis(pentyloxy)triphenyleno[1 ,2-d]oxazole. Compound 40 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCI3) 10.14 (1 H, s), 8.82 (1 H, s), 8.51 (1 H, dd, J 8.6, 1.7), 8.06 - 8.03 (2H, m), 7.91 - 7.80 (5H, m), 7.57 - 7.55 (2H, m), 4.59 (2H, t, J 5.5 Hz), 4.41 (2H, t, J 6.7 Hz), 4.29 - 4.20 (6H, m), 4.15-4.10 (2H, m), 3.87-3.82 (2H, m), 3.69-3.57 (4H, m), 3.30-3.21 (2H, m), 2.05 - 1.93 (8H, m), 1.63 - 1.45 (16H, m), 1.05 - 0.98 (12H, m) ppm. 13 C NMR 6c: (100 MHz, CDCb) 161.7, 149.4, 148.8, 145.9, 145.4, 142.9, 140.8, 140.2, 134.7, 133.2, 129.1, 128.7, 128.0, 127.9, 127.6, 127.1 , 126.9, 124.8, 124.7, 124.6, 124.0,

123.6, 123.4, 116.4, 112.7, 108.1 , 107.2, 103.7, 103.6, 72.5, 70.7, 70.4, 70.1 , 69.9, 69.8, 69.7, 69.0,

50.6, 29.32, 29.30, 29.17, 28.54, 28.46, 28.43, 22.75, 22.71 , 14.27, 14.21 ppm. MALDI m/z: 912.9 ([M] + 100%), 913.9 ([M+H] + 90%). Elemental analysis Found: C, 73.36; H, 7.55; N, 6.12 %. C55H68N4O8 requires C, 73.34; H, 7.51 ; N, 6.14 %.

Method of Synthesising Compound 41

Compound 41 was synthesised using the following method. A slurry of Precursor 8 (100 mg, 0.13 mmol) and K2CO3 (37 mg, 0.26 mmol) in MeCN (5 ml_) was heated at reflux with a CaC drying tube for 0.5 h followed by addition of 2-(2-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)ethoxy) ethyl 4- methylbenzenesulfonate (101 mg, 0.26 mg). The resultant slurry was further heated at reflux for 24 h. The reaction mixture was allowed to cool to room temperature and the precipitate filtered off via suction filtration. The solvent was evaporated from the filtrate to dryness in vacuo and the crude solid was purified by purified via flash column chromatography (silica, silica, 50 % EtOAc: 50 % n- hexane) to afford Compound 38 as a yellow solid (15 mg, 13 %).

The name for Compound 41 is 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12- tetrakis(pentyloxy)triphenyleno[1 ,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)ethan-1 -amine.

Compound 41 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCI3) 10.13 (1 H, s), 8.82 (1H, s), 8.50 (1 H, dd, J 8.6, 1.7), 8.07 - 8.03 (2H, m), 7.91 - 7.81 (5H, m), 7.57 - 7.57 (2H, m), 4.58 (2H, t, J 5.5 Hz), 4.43 (2H, t, J 6.7 Hz), 4.28 - 4.20 (6H, m), 4.14-4.10 (2H, m), 3.86-3.82 (2H, m), 3.69-3.57 (4H, m), 3.17-3.19 (2H, m), 2.04 - 1.92 (8H, m), 1.63 - 1.44 (16H, m), 1.04 - 0.97 (12H, m) ppm. 13 C NMR 5c: (100 MHz, CDC ) 161.7, 149.4, 148.8, 145.9, 145.4, 142.9, 140.8, 140.2, 134.7, 133.2, 129.1, 128.7, 128.0, 127.9, 127.6, 127.1 , 126.9, 124.8, 124.7, 124.6, 124.0,

123.6, 123.4, 116.4, 112.7, 108.1 , 107.2, 103.7, 103.6, 72.3, 70.6, 70.3, 70.0, 69.9, 69.8, 69.7, 69.0, 42.5, 29.4, 29.3, 29.2, 28.5, 28.5, 28.4, 22.75, 22.7, 14.3, 14.2 ppm. MALDI m/z: 886.5 ([M] + 100%), 887.6 ([M+H] + 70%).

Method of Synthesising Compound 44

Compound 44 was synthesised using the following method. A solution of Precursor 2 (100 mg, 0.132 mmol), 3-fluorobenzoyl chloride (92 mg, 0.658 mmol) and N,N-diisopropylethylamine (0.1 rriL, 0.574 mmol) in PhMe (5 rriL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo purified via flash column chromatography (silica, 60 % CH2CI2: 40 % n- hexane) to afford an intermediate as a brown solid (19 mg, 18 %).

The intermediate (3-fluoro-N-(2,3,6,7,10,11-hexakis(pentyloxy)triphenylen-1-y l)benzamide) (100 mg, 0.11 mmol) was dissolved in xylenes (10 ml_) and Woollins reagent (117.8 mg, 0.22 mmol) was added to the flask. The reaction was stirred at reflux for 24 h before being cooled to room temperature causing the formation of a grey precipitate. The contents of the flask were filtered through filter paper and the filtrate recovered. The filtrate was evaporated to dryness and purified by column chromatography (silica, 40% dichloromethane : hexane) and (silica, 1% acetone : hexane) yielding 8-(3-fluorophenyl)-2,3,6,11 ,12-pentakis(pentyloxy)triphenyleno[1 ,2-d][1,3]selenazole as a yellow solid (1.8 mg).

The name for Compound 44 is 8-(3-fluorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyle no[1 ,2- d][1,3]selenazole.

Compound 44 had the following characterisation data: 1 H NMR 6H (500 MHz, CDCI3) 10.40 (1H, s), 8.00 (1H, s), 7.97 (1 H, d, J 9.8 Hz), 7.95 (1H, s), 7.92 (1 H, s), 7.90 (1 H, d, J 7.8 Hz), 7.87 (1H, s), 7.49 (1H, dd, J 14.1 , 8.5 Hz), 7.24 - 7.21 (1H, m), 4.45 (2H, t, J 6.8 Hz), 4.42 (2H, t, J 6.7 Hz), 4.28 (6H, dt, J 13.4, 6.6 Hz), 2.06 - 1.94 (10H, m), 1.61-1.44 (20H, m), 1.03 - 0.93 (15H, m) ppm. TOF LD + m/z = 860.4 ([M+2+H] + 30 %), 859.4 ([M+2] + 60 %), 858.4 ([M+H] + 90 %), 857.4 ([M] + 100 %),

856.4 ([M-2+H] + 40 %), 855.4 ([M-2] + 60 %), 854.4 ([M-3] + 30 %), 825.5 ([TpOxPhmF + MeOH] + ),

793.4 ([TpOxPhmF] + ).

Method of Synthesising Compound 45

Compound 45 was synthesised using the following method. Precursor 2 (190 mg, 0.25 mmol, 1 eq) and 4-methoxybenzoyl chloride (213 mg, 1.25 mmol, 5 eq) were dissolved in dry toluene (7 ml_) and N,N-disopropylethylamine (0.2 mL, 1.25 mmol, 5 eq) was added. The solution was stirred and heated to reflux under a CaCh drying tube for 2h. The solution was then evaporated to dryness and the crude solid was heated to 240° C for 10 mins. The crude product was recrystalised (dichloromethane : hexane, 1 : 5) and then purified by silica plug (60% dichloromethane : hexane) to yield 8-(4- methoxyphenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole as an off white solid (53 mg, 26%).

The name for Compound 45 is 8-(4-methoxyphenyl)-2,3,6,11 ,12- pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole.

Compound 45 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 10.15 (1 H, s), 8.32 (2H, d, J 8.9 Hz), 7.93 - 7.87 (4H, m), 7.06 (2H, d, J 8.9 Hz), 4.46 (4H, t, J 7.0 Hz), 4.28 - 4.24 (6H, m), 3.93 (3H, s), 2.12 - 1.94 (10H, m), 1 .65 - 1.43 (20H, m), 1 .03 - 0.96 (15H, m) ppm. MALDI m/z: 804.9 ([M] + 100%), 805.9 ([M+H] + 70%), 806.9 ([M+1+H] + 25%).

Method of Synthesising Compound 46

Compound 46 was synthesised using the following method. A solution of Precursor 1 (100 mg, 0.132 mmol), benzoyl chloride (92 mg, 0.658 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo purified via flash column chromatography (silica, 60 % CH2CI2: 40 % n- hexane) to afford an intermediate as a brown solid (19 mg, 18 %).

The intermediate had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 8.55 (1 H, s), 8.45 (1 H, s), 8.07 (2H, d, J 7.5 Hz), 7.78 (1 H, s), 7.74 (1 H, s), 7.72 (1 H, s), 7.71 (1 H, s), 7.59 (1 H, d, J 7.0 Hz), 7.54 (2H, t, J 7.4 Hz), 4.28 - 4.12 (10H, m), 3.67-3.54 (2H, m), 2.00 - 1.85 (8H, m), 1.70 - 1.37 (20H, m), 1.34 - 1.06 (8H, m), 1.02 - 0.90 (12H, m), 0.83 (3H, t, J 7.0 Hz), 0.75 (3H, t, J 7.1 Hz) ppm. 13 C NMR da: (100 MHz, CDCh) 174.6, 151.0, 149.7, 148.7, 148.4, 148.4, 144.0,

135.1, 131.7, 130.9, 128.5, 127.9, 126.6, 124.7, 124.2, 123.0, 122.6, 122.0, 110.3, 108.1, 107.7, 106.8, 106.7, 73.4, 70.1, 70.0, 69.5, 69.3, 68.8, 32.1, 30.1 , 29.9, 29.6, 29.4, 29.3, 28.7, 28.5, 28.5,

28.1, 22.9, 22.7, 22.6, 14.3, 14.3, 14.1 ppm. MALDI m/z: 863.3 ([M]+ 100%).

A solution of the intermediate (100 mg, 0.116 mmol) and Lawesson’s Reagent (175 mg, 0.658 mmol) in PhMe (5 mL) was heated to and held at reflux for 48 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 mins under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 46 as a green solid (17 mg, 19 %).

The name for Compound 46 is 2,3,6, 11 ,12-pentakis(pentyloxy)-8-phenyltriphenyleno[1 ,2-d]thiazole.

Compound 46 had the following characterisation data: 1 H NMR 6H: (300 MHz, CDCh) 10.51 (1H, s), 8.24 - 8.22 (2H, m), 7.92-7.89 (3H, m), 7.76 (1H, s), 7.53 - 7.52 (3H, m), 4.43 - 4.26 (10H, m), 2.10 1.95 (10H, m), 1.66 - 1.57 (10H, m), 1.53 - 1.47 (10H, m), 1.03 -1.00 (15H, m) ppm. 13 C NMR 6c: (100 MHz, CDCh) 166.4, 152.5, 151.5, 150.2, 149.3, 148.3, 134.7, 130.9, 130.0, 129.3, 127.6, 125.7, 125.4, 124.7, 123.8, 119.0, 112.4, 108.9, 107.2, 106.9, 100.9, 70.3, 70.2, 69.7, 69.2, 69.1, 29.7, 29.6, 29.6, 29.5, 29.4, 28.8, 28.8, 28.8, 23.1 , 23.0, 23.0, 23.0 23.0, 14.5, 14.5, 14.5, 14.5 ppm. MALDI m/z: 791.56 ([M]+ 100%).

Method of Synthesising Compound 47

Compound 47 was synthesised using the following method. A solution of Precursor 1 (100 mg, 0.132 mmol), 4-cyanobenzoyl chloride (109 mg, 0.658 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 ml.) was heated to and held at reflux for 18 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The crude brown solid was added to a solution of Lawesson’s Reagent (175 mg, 0.658 mmol) in PhMe (5 mL) was heated to and held at reflux for 48 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 mins under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 40 % CH2CI2: 60 % n- hexane) to afford Compound 47 as a yellow solid (5 mg, 5 %). The name for Compound 47 is 4-(2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d]thiazol -8- yl)benzonitrile.

Compound 47 had the following characterisation data: 1 H NMR 6 H : (300 MHz, CDCI3) 10.38 (1H, s), 8.31 (2H, d, J 8.4 Hz), 7.97 - 7.88 (4H, m), 7.79 (1 H, d, J 8.5 Hz), 4.41 - 4.26 (1 OH, m), 2.06 - 1.95 (10H, m), 1.61 - 1.55 (10H, m), 1.51 - 1.44 (10H, m), 1.03 - 0.97 (15H, m) ppm. MALDI m/z: 816.9

([M]+ 90%), 817.9 ([M+H]+ 100%).

Referring below to Table 1, there is shown luminescent data for Compounds 1 to 6. Referring now to Tables 2 to 4, there is provided luminescence data for pairs of compounds which are capable of absorbing at the same wavelength and emitting at different wavelengths.

Table 2: Luminescence data for pair 1 Table 3: Luminescence data for pair 2

Table 4: Luminescence data for pair 3 Solvent e G Viscosity Compound Compound Compound Compound 4 Compound Compound 6

Ethyl 6.0 0.45 Absorption Amax 281 270 272 275 272 253 acetate (nm)

Emission Amax 367 467 494 510 536 594 (nm) pSS (cm ·1 ) 8300 15600 16500 16800 18100 22700

F 0.18 ± 0.01 0.46 ± 0.04 0.55 ± 0.05 0.48 ± 0.04 0.51 ± 0.04 †

Brightness (M _1 29 ± 5 51 ± 5 92 ± 9 56 ± 5 53 ± 5 † cm -1 )

Octan-1-ol 10. 7.36 Absorption Amax 281 271 272 275 270 255

3 (nm)

Emission Amax 367 473 497 515 526 384 (nm) pSS (cm -1 ) 8300 15800 16600 17000 18000 13200

F 0.30 ± 0.03 0.61 ± 0.06 0.71 ± 0.07 0.55 ± 0.05 0.56 ± 0.05 †

Brightness (M _1 36 ± 7 64 ± 6 91 ± 9 67 ± 7 50 ± 5 † cm 1 )

Acetonitrile 37. 0.38 Absorption Amax 281 270 273 275 270 253

5 (nm)

Emission Amax 367 492 524 543 592 630 (nm) pSS (cm -1 ) 8300 16700 17600 18000 20200 23650

F 0.20 ± 0.02 0.46 ± 0.04 0.51 ± 0.05 0.36 ± 0.04 0.21 ± 0.02 †

Brightness (M _1 12 ± 2 38 ± 4 44 ± 4 30 ± 3 t † cm 1 )

† No value could be obtained $ No value could be obtained due to poor solubility and therefore no e data.

Table 1 Luminescent data for Compounds 1 to 6

Examples

Referring now to the below Table, there is shown the composition of objects comprising a material, the material comprising a polymer and a luminescent compound according to Examples 1a to 5d of the invention. Comparative Examples 6a to 6f using fluorescein in PMMA are also shown. The emission spectra for each Example and Comparative Example is shown in the Figures listed.

The objects were fabricated by dissolving the polymer and the luminescent compound in chlorobenzene in different w/w ratios. The resulting solution was spin coated onto a quartz slide to form a film. The quartz slides were purchased from UQG Optics Ltd (Cambridge, UK) (20 x 20mm or 15mm x 15 mm, thickness ~ 1.1. mm).

Referring now to Figures 1 to 5, there is shown the emission spectra of the objects according to the Examples 1a to 5d upon excitation at 286nm. Referring also to Figure 6, there is shown the emission spectra of the objects according to Comparative Examples 6a to 6f.

It is shown in Figure 1 that there is a blue shift as the concentration of the luminescent compound decreases in the polymer of Examples 1a to 1f. Without wishing to be bound by any particular theory, it is thought at high concentrations of luminescent compound, the emission results from excimer or aggregate emissions. In contrast, at low concentrations of luminescent compound, the emission results from the monomer, which results in the blue shift. The blue shift was also observed for Examples 2a to 2f (PMMA), Examples 3a to 3d (PHS), and Examples 5a to 5d (PS). However, no blue shift was observed for Examples 4a to 4e when the polymer is PEG. It is shown in Figure 3 that there is a photophysical interaction between the polymer and the luminescent compound. The blank spectrum shows the emission of the polymer only. The emission at 350nm originates from the polymer. However, this interaction is completely absent at higher concentrations of luminescent compound.

Referring now to Figure 7, there is shown a graph 7 illustrating the shift in emission peak vs. the relative ratio of Compound 3 in PMMA.

Referring now to Figure 8A and 8B, there is shown two photographs 8A, 8B of polymer doped with the luminescent compound, Compound 2. Black and grey Coca Cola (RTM) bottle caps were melted and doped with Compound 2 in a w/w ratio of 100:1 polymer to dye. The photograph 8A shows the emission of doped grey plastic 8a and doped black plastic 8b in daylight. The photograph 8B shows the emission of doped grey plastic 8a’ and doped black plastic 8b’ under UV light. It is shown that the emission from the grey plastic was strong and it was difficult to look at it directly. The emission from the black polymer was weaker but was still visible.

It will be appreciated by those skilled in the art that any number of combinations of the aforementioned features and/or those shown in the appended drawings provide clear advantages over the prior art and are therefore within the scope of the invention described herein.