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Title:
A SYSTEM AND METHOD USING PHOTOCHEMICAL OXYGEN STORAGE AND RELEASE
Document Type and Number:
WIPO Patent Application WO/2021/041430
Kind Code:
A4
Abstract:
Disclosed herein is a method for converting light energy into mechanical energy and/or oxygen storage, purification, isolation, concentration, and/or removed. The method may comprise exposing a mixture of a polycyclic aromatic compound and a photosensitizer to oxygen and light to form an endoperoxide, and decomposing the endoperoxide to reform the polycyclic aromatic compound and oxygen. The polycyclic aromatic compound may be a naphthalene compound or anthracene compound and/or may have a formula (I).

Inventors:
MCCORMICK THERESA (US)
LUTKUS LUKE (US)
Application Number:
PCT/US2020/047829
Publication Date:
May 06, 2021
Filing Date:
August 25, 2020
Export Citation:
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Assignee:
UNIV PORTLAND STATE (US)
International Classes:
A61K41/00; B01J8/26; B01J8/42; C01B13/02
Attorney, Agent or Firm:
BURGESS, Steven J. et al. (US)
Download PDF:
Claims:
AMENDED CLAIMS received by the International Bureau on 08 March 2021 (08.03.2021)

We claim:

1. A method, comprising: exposing a first mixture comprising a polycyclic aromatic compound and a photosensitizer to a first portion of oxygen gas and light at a first temperature to form a second mixture comprising an endoperoxide, the first temperature being selected to substantially prevent the endoperoxide from decomposing; raising a temperature of the second mixture to a second temperature higher than the first temperature and/or stopping irradiation to facilitate decomposition of the endoperoxide to form a regenerated polycyclic aromatic compound and release oxygen; and mixing the released oxygen with an air stream to form an oxygen enriched air stream.

2. The method of claim 1 , wherein exposing the first mixture to oxygen gas comprises exposing the first mixture to ambient air.

3. The method of claim 1, wherein the method further comprises providing the oxygen enriched air stream to a patient in need thereof.

4. The method of claim 1 , further comprising maintaining the second mixture at or below the first temperature for a selected time period before raising the temperature of the second mixture to the second temperature.

5. The method of claim 1, further comprising exposing the regenerated polycyclic aromatic compound and the photosensitizer to a second portion to oxygen gas to reform at least a portion of the endoperoxide.

6. The method of claim 1, comprising: a) exposing a first mixture comprising a first polycyclic aromatic compound and a first photosensitizer to a first portion of oxygen gas and light from a first light source at a first temperature to form a second mixture comprising a first endoperoxide, the first temperature being selected to substantially prevent decomposition of the first endoperoxide;

AMENDED SHEET (ARTICLE 19) b) raising a temperature of the second mixture to a second temperature that is higher than the first temperature suitable to decompose the first endoperoxide thereby regenerating at least a portion of the first polycyclic aromatic compound and forming a second portion of oxygen gas that is mixed with a first air stream to form a first oxygen enriched air stream; c) exposing a third mixture comprising a second polycyclic aromatic compound and a second photosensitizer to a third portion of oxygen gas and light from a second light source at a third temperature to form a fourth mixture comprising a second endoperoxide, the third temperature being selected to substantially prevent decomposition of the second endoperoxide; d) when the first endoperoxide has substantially decomposed, raising a temperature of the third mixture to a fourth temperature that is higher than the third temperature and selected to decompose the second endoperoxide, thereby regenerating at least a portion of the second polycyclic aromatic compound and forming a fourth portion of oxygen gas that is mixed with a second air stream to form a second oxygen enriched air stream; and e) exposing the first polycyclic aromatic compound and the first photosensitizer to a fifth portion of oxygen gas and light from the first light source to reform at least a portion of the first endoperoxide.

7. The method of claim 6, wherein step b is performed contemporaneously with step c.

8. A method, comprising: exposing a first mixture comprising a polycyclic aromatic compound, a photosensitizer and oxygen gas to light in an enclosed space having a first volume to form an endoperoxide by a reaction between the polycyclic aromatic compound and the oxygen gas, thereby changing a volume of the enclosed space to a second volume that is less than the first volume; and stopping irradiation by the light to regenerate the polycyclic aromatic compound, and release at least a portion of the oxygen gas into the enclosed space thereby changing the volume of the enclosed space to a third volume that is substantially the same as the first volume.

9. The method of claim 8, wherein changing the volume of the enclosed space moves a piston.

AMENDED SHEET (ARTICLE 19)

10. The method of claim 8, further comprising exposing the regenerated polycyclic aromatic compound to light to reform at least a portion of the endoperoxide, and then removing the light source to regenerate the polycyclic aromatic compound.

11. The method of claim 8, wherein exposing the first mixture to the light is performed at a first temperature and removing the light further comprises raising the temperature to a second temperature higher than the first temperature.

12. A method, comprising: exposing a first mixture comprising a polycyclic aromatic compound, a photosensitizer and oxygen gas to light in an enclosed space having a first pressure to form an endoperoxide by a reaction between the polycyclic aromatic compound and the oxygen gas, thereby changing a pressure in the enclosed space to a second pressure that is less than the first pressure; and stopping irradiation by the light to regenerate the polycyclic aromatic compound, and release at least a portion of the oxygen gas into the enclosed space thereby changing the pressure of the enclosed space to a third pressure that is substantially the same as the first pressure.

13. The method of claim 12, wherein changing the pressure of the enclosed space results in work.

14. The method of claim 12, further comprising exposing the regenerated polycyclic aromatic compound to light to reform at least a portion of the endoperoxide, and then removing the light source to regenerate the polycyclic aromatic compound.

15. The method of claim 12, wherein exposing the first mixture to the light is performed at a first temperature and removing the light further comprises raising the temperature to a second temperature higher than the first temperature.

16. The method of any one of claims 1-15, wherein the polycyclic aromatic compound is a naphthalene compound or an anthracene compound.

AMENDED SHEET (ARTICLE 19)

37

17. The method of claim 16, wherein the polycyclic aromatic compound has a formula I wherein: each of R1, R2 and R3 independently is H, OH, aliphatic, aryl, alkoxy, -O-acyl, -O- Si(alkyl)3, -O-amino acid, or -O-carbohydrate; n is from 0 to 6; and

” represents a bond that may or may not be present.

18. The method of claim 17, wherein the compound has a formula selected from

II III.

19. The method of claim 17, wherein n=0.

20. The method of claim 17, wherein at least one of R1 and R2 are not H.

21. The method of claim 20, wherein R1 and R2 are both alkyl.

22. The method of claim 20, wherein R1 and R2 are the same and not H.

23. The method of claim 16, wherein the polycyclic aromatic compound is 1,4- dimethylnaphthalene.

AMENDED SHEET (ARTICLE 19)

38

24. The method of claim 16, wherein the first temperature is from -78 °C to 25 °C.

25. The method of claim 24, wherein the first temperature is from 0 °C to 20 °C.

26. The method of claim 16, wherein the second temperature is from -40 °C to 100

°C.

27. The method of claim 26, wherein the second temperature is from 15 °C to 25 °C.

28. The method of any one of claims 1-15, wherein the photosensitizer is rose bengal, methylene blue, Eosin B, Ru(bpy)3, methyl green, rubrene, a fluorene, a fullerene, a nanoparticle or a combination thereof.

29. The method of claim 28, wherein: the fullerene is a C20-94 fullerene, optionally substituted with alkyl, aryl, alkoxy or a combination thereof; the fluorene is 9,9-substituted fluorene or 2,7-substitued fluorene; and the nanoparticle is a CdTe, ZnSe, SiNP, CNP, AuNP, or BiNP nanoparticle, is a silica, protein or polymer nanoparticle that comprises a triplet photosensitizer, or a combination thereof.

30. The method of claim 28, wherein the photosensitizer is rose bengal.

31. The method of any one of claims 1-15, wherein the light comprises light having a wavelength of from 380 nm to 1000 nm.

32. The method of claim 31, wherein the light is visible light.

33. The method of claim 32, wherein the visible light has a wavelength of from 380 nm to 740 nm.

AMENDED SHEET (ARTICLE 19)

39

34. The method of claim 33, wherein the visible light comprises light having a wavelength of from 530 nm to 575 nm.

35. The method of any one of claims 1-15, wherein the light comprises natural light.

36. The method of claim 35, wherein the light is solar light.

37. The method of any one of claims 1-15, wherein the light comprises light from an LED light source.

38. The method of any one of claims 1-15, wherein the first mixture is a solution and further comprises a solvent.

39. The method of claim 38, wherein the solvent is acetonitrile, ethanol, methanol, dichloromethane, hexanes, water, ether, dimethylformamide, carbon tetrachloride, chloroform, propylene carbonate, ethylene glycol, propylene glycol, tetrahydrofuran or a combination thereof.

40. The method of claim 38, wherein the solvent is acetonitrile.

41. The method of any one of claims 1-15, wherein the first mixture is a solid.

42. The method of claim 41, wherein the solid further comprises a zeolite, diatomaceous earth, hydrogel, polymer, metal-organic framework motif, or a combination thereof.

43. The method of claim 42, wherein the polymer comprises polyethylene, polypropylene, polyethylene glycol, polypropylene glycol, a peptide, a polyacrylic acid, or a combination thereof.

AMENDED SHEET (ARTICLE 19)

40

44. The method of claim 43, wherein the polymer has a molecular weight of from 5 kDa to 500 kDa.

45. A system, comprising: a first chamber comprising a first mixture comprising a first polycyclic aromatic compound and a first photosensitizer, a first gas inlet, a first gas outlet, a first pump, and a first light source; a second chamber comprising a second mixture of a first polycyclic aromatic compound and a second photosensitizer, a second gas inlet, a second gas outlet, a second pump, and a second light source; and a controller configured to switch an air stream between the first and second gas inlets.

46. The system of claim 45, further comprising a temperature controller.

47. The system of claim 46, wherein the temperature controller is a heater, a cooler, or a combination thereof.

AMENDED SHEET (ARTICLE 19)

41