Title:
TETRAKIS(DIMETHOXYPHENYL)ADAMANTANE (TDA) AND ITS INCLUSION COMPLEXES
Document Type and Number:
WIPO Patent Application WO/2016/139373
Kind Code:
A1
Abstract:
Molecular storage materials for incorporating small molecules in solid matrices may find applications in structure elucidation, decontamination, and slow release of active ingredients. The syntheses of 1,3,5,7-tetrakis(2,4-dimethoxyphenyl)adamantane (TDA), 1,3,5,7-tetrakis(4-methoxyphenyl)adamantane, 1,3,5,7-tetrakis(4-methoxy-2-methylphenyl)adamantane, and 1,3,5,7-tetrakis(4-methoxy-2-ethylphenyl)adamantane are reported, together with details on their X-ray crystal structures. All four adamantanes crystallize readily. The octaether shows an unusual level of pseudopolymorphism in the solid state,and includes a wide range of different guest molecules in its crystal lattices. Thus far, 20 different inclusion complexes with guest molecules ranging from methanol or trifluorobenzene were characterized. Both nitromethane and benzene were taken up into inclusion materials and were shown to be released by one of three different processes.
Inventors:
RICHERT CLEMENS (DE)
FREY WOLFGANG (DE)
SCHWENGER ALEXANDER (DE)
FREY WOLFGANG (DE)
SCHWENGER ALEXANDER (DE)
Application Number:
PCT/EP2016/054833
Publication Date:
September 09, 2016
Filing Date:
March 07, 2016
Export Citation:
Assignee:
RICHERT CLEMENS (DE)
FREY WOLFGANG (DE)
SCHWENGER ALEXANDER (DE)
FREY WOLFGANG (DE)
SCHWENGER ALEXANDER (DE)
International Classes:
C07C43/21; B01J20/22; C07C9/15; C07C13/18; C07C15/04; C07C19/03; C07C19/04; C07C25/13; C07C31/08; C07C31/10; C07C31/125; C07C49/08; C07C205/02; C07C205/06; C07C211/46; C07C255/03; C07D295/192; C07D499/12
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GRIESSER; M. TOLEV; A. SINGH; T. SABIROV; C. GERLACH; C. RICHERT, J. ORG. CHEM., vol. 77, 2012, pages 2703
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W. HOFMAN; L. STEFANIAK; T. URBANSKI; M. WITANOWSKI, J. AM. CHEM. SOC., vol. 86, 1964, pages 554
S. A. KOLDUNOV; A. V. ANANIN; V. A. GARANIN; V. A. SOSIKOV; S. 1. TORUNOV, CENTRAL EUROPEAN JOURNAL OF ENERGETIC MATERIALS, vol. 6, 2009, pages 1
H. STETTER; C. WULFF, CHEM. BER., vol. 93, 1960, pages 1366
H. STETTER; M. KRAUSE, LIEBIGS NN. CHEM., vol. 717, 1968, pages 60
MICHAEL MASTALERZ: "Permanent Porous Materials from Discrete Organic Molecules-Towards Ultra-High Surface Areas", CHEMISTRY - A EUROPEAN JOURNAL., vol. 18, no. 33, 13 August 2012 (2012-08-13), WEINHEIM, DE, pages 10082 - 10091, XP055275000, ISSN: 0947-6539, DOI: 10.1002/chem.201201351
NADINE PANNIER ET AL: "RigidC3-Symmetric Scaffolds Based on Adamantane", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2008, no. 7, 1 March 2008 (2008-03-01), DE, pages 1278 - 1284, XP055274939, ISSN: 1434-193X, DOI: 10.1002/ejoc.200701003
ALEXANDER SCHWENGER ET AL: "Tetrakis(dimethoxyphenyl)adamantane (TDA) and Its Inclusion Complexes in the Crystalline State: A Versatile Carrier for Small Molecules", CHEMISTRY - A EUROPEAN JOURNAL., vol. 21, no. 24, 8 June 2015 (2015-06-08), WEINHEIM, DE, pages 8781 - 8789, XP055274923, ISSN: 0947-6539, DOI: 10.1002/chem.201406568
J. D. WUEST, CHEM. COMMUN., 2005, pages 5830
W. LU; D. YUAN; D. ZHAO; C. SCHILLING; O. PLIETZSCH; T. MULLER; S. BRASE; J. GUENTHER; J. BLÜMEL; R. KRISHNA, CHEM. MATER., vol. 22, 2010, pages 5964
H. ZHAO; Z. JIN; H. SU; J. ZHANG; X. YAO; H. ZHAO; G. ZHU, CHEM. COMMUN., vol. 49, 2013, pages 2780
M. MASTALERZ, CHEM. EUR. J., vol. 18, 2012, pages 10082
T. BEN; H. REN; S. MA; D. CAO; J. LAN; X. JING; W. WANG; J. XU; F. DENG; J. M. SIMMONS, ANGEW. CHEM. LNT. ED, vol. 48, 2009, pages 9457
D. YUAN; W. LU; D. ZHAO; H.-C. ZHOU, ADV. MAT., vol. 23, 2011, pages 3723
A. P. KATSOULIDIS; M. G. KANATZIDIS, CHEM. MAT, vol. 23, 2011, pages 1818
G. ZHANG; M. MASTALERZ, CHEM. SOC. REV., vol. 43, 2014, pages 1934
V. R. REICHERT; L. J. MATHIAS, MACROMOLECULES, vol. 27, 1994, pages 1030
V. R. REICHERT; L. J. MATHIAS, MACROMOLECULES, vol. 27, 1994, pages 7015
0. ERMER, J. AM. CHEM. SOC., vol. 110, 1988, pages 3747
E. GALOPPINI; R. GILARDIB, CHEM. COMMUN., 1999, pages 173
C. I. SCHILLING; O. PLIETZSCH; M. NIEGER; T. MULLER; S. BRASE, EUR . ORG. CHEM., vol. 9, 2011, pages 1743
O. PLIETZSCH; C. I. SCHILLING; M. TOLEV; M. NIEGER; C. RICHERT; T. MULLER; S. BRASE, ORG. BIOMOL. CHEM., vol. 7, 2009, pages 4734
A. SINGH; M. TOLEV; M. MENG; K. KLENIN; O. PLIETZSCH; C. I. SCHILLING; T. MULLER; M. NIEGER; S. BRASE; W. WENZEL, ANGEW. CHEM. LNT. EOL., vol. 50, 2011, pages 3227
A. SINGH; M. TOLEV; C. I. SCHILLING; S. BRASE; H. GRIESSER; C. RICHERT, J. ORG. CHEM., vol. 77, 2012, pages 2718
GRIESSER; M. TOLEV; A. SINGH; T. SABIROV; C. GERLACH; C. RICHERT, J. ORG. CHEM., vol. 77, 2012, pages 2703
A. SCHWENGER; C. GERLACH; H. GRIESSER; C. RICHERT, J. ORG. CHEM., vol. 79, 2014, pages 11558
Z. TAKÀTS; I. COTTE-RODRIGUEZ; N. TALATY; H. CHEN; R. G. COOKS, CHEM. COMMUN., vol. 15, 2005, pages 1950
T. NADDO; Y. CHE; W. ZHANG; K. BALAKRISHNAN; X. YANG; M. YEN; J. ZHAO; J. S. MOORE; L. ZANG, J. AM. CHEM. SOC., vol. 129, 2007, pages 6978
J. D. RODGERSA; N. J BUNCE, WATERRES, vol. 35, 2001, pages 2101
J. M. SCHNORR; D. VAN DER ZWAAG; J. J. WALISH; Y. WEIZMANN; T. M. SWAGER, ADV. FUNCT. MAT., vol. 23, 2013, pages 5285
W. HOFMAN; L. STEFANIAK; T. URBANSKI; M. WITANOWSKI, J. AM. CHEM. SOC., vol. 86, 1964, pages 554
S. A. KOLDUNOV; A. V. ANANIN; V. A. GARANIN; V. A. SOSIKOV; S. 1. TORUNOV, CENTRAL EUROPEAN JOURNAL OF ENERGETIC MATERIALS, vol. 6, 2009, pages 1
H. STETTER; C. WULFF, CHEM. BER., vol. 93, 1960, pages 1366
H. STETTER; M. KRAUSE, LIEBIGS NN. CHEM., vol. 717, 1968, pages 60
Attorney, Agent or Firm:
KISTERS, Michael (Dortmund, DE)
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