Linked bis-isophthalic acid derivatives as building blocks in the design of self-assembling structures

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2327-2330

  Zafar, Abdullah ^a   Yang, Ji ^a   Geib, Steven J ^a   Hamilton, Andrew D ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; ISOPHTHALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; REACTION ANALYSIS;

EID: 0029968094     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00287-0     Document Type: Article

References (28)

1. For recent reviews see; Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science (Washington, D.C.) 1992, 254, 1312. Lindsey, J. S. New J. Chem. 1991, 15, 153.
2. For recent reviews see; Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science (Washington, D.C.) 1992, 254, 1312. Lindsey, J. S. New J. Chem. 1991, 15, 153.
3. For recent reviews see; Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science (Washington, D.C.) 1992, 254, 1312. Lindsey, J. S. New J. Chem. 1991, 15, 153.
4. Desiraju, G. R. Angew. Chem. Int. Ed. Engl. 1995, 34, 2311. Fredericks, J.; Yang, J.; Geib, S. J.; Hamilton, A. D. Proc. Indian. Acad. Sci. (Chem. Sci) 1994, 106, 923.
5. Desiraju, G. R. Angew. Chem. Int. Ed. Engl. 1995, 34, 2311. Fredericks, J.; Yang, J.; Geib, S. J.; Hamilton, A. D. Proc. Indian. Acad. Sci. (Chem. Sci) 1994, 106, 923.
6. For the designed stabilization of cavity structure by hydrogen bonding see, for example; Kimizuka, N.; Fujikawa, S.; Kuwahara, H.; Kunitake, T.; Marsh, A.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1995, 2103. Wang, X.; Simarel, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119. Mahdyarfar, A.; Harris, K. D. J. Chem. Soc. Chem. Commun. 1993, 51-3. By metal chelation see; Venkataraman, D.; Gardner, G. B.; Lee, S.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600. Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116 1151.
7. For the designed stabilization of cavity structure by hydrogen bonding see, for example; Kimizuka, N.; Fujikawa, S.; Kuwahara, H.; Kunitake, T.; Marsh, A.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1995, 2103. Wang, X.; Simarel, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119. Mahdyarfar, A.; Harris, K. D. J. Chem. Soc. Chem. Commun. 1993, 51-3. By metal chelation see; Venkataraman, D.; Gardner, G. B.; Lee, S.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600. Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116 1151.
8. For the designed stabilization of cavity structure by hydrogen bonding see, for example; Kimizuka, N.; Fujikawa, S.; Kuwahara, H.; Kunitake, T.; Marsh, A.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1995, 2103. Wang, X.; Simarel, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119. Mahdyarfar, A.; Harris, K. D. J. Chem. Soc. Chem. Commun. 1993, 51-3. By metal chelation see; Venkataraman, D.; Gardner, G. B.; Lee, S.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600. Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116 1151.
9. For the designed stabilization of cavity structure by hydrogen bonding see, for example; Kimizuka, N.; Fujikawa, S.; Kuwahara, H.; Kunitake, T.; Marsh, A.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1995, 2103. Wang, X.; Simarel, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119. Mahdyarfar, A.; Harris, K. D. J. Chem. Soc. Chem. Commun. 1993, 51-3. By metal chelation see; Venkataraman, D.; Gardner, G. B.; Lee, S.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600. Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116 1151.
10. For the designed stabilization of cavity structure by hydrogen bonding see, for example; Kimizuka, N.; Fujikawa, S.; Kuwahara, H.; Kunitake, T.; Marsh, A.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1995, 2103. Wang, X.; Simarel, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119. Mahdyarfar, A.; Harris, K. D. J. Chem. Soc. Chem. Commun. 1993, 51-3. By metal chelation see; Venkataraman, D.; Gardner, G. B.; Lee, S.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600. Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116 1151.
11. Müller, A.; Reuter, H.; Dillinger, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 2328. MacNicol, D. D. In Inclusion Compounds; Atwood, J. L.; Davies, J.E.D.; MacNicol, D.D., Eds.; Academic Press: London, 1984; Vol. 2, pp 1-45.
12. Müller, A.; Reuter, H.; Dillinger, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 2328. MacNicol, D. D. In Inclusion Compounds; Atwood, J. L.; Davies, J.E.D.; MacNicol, D.D., Eds.; Academic Press: London, 1984; Vol. 2, pp 1-45.
13. For a recent extensive discussion of the crystal packing behavior of trimesic acid and its derivatives see Herbstein, F. H. in Comprehensive Supramolecular Chemistry, Pergamon Press, Oxford. Volume 6. In Press. See also, Duchamp, D. J.; Marsh, R. E. Acta. Cryst. 1969, B25, 5.
14. For a recent extensive discussion of the crystal packing behavior of trimesic acid and its derivatives see Herbstein, F. H. in Comprehensive Supramolecular Chemistry, Pergamon Press, Oxford. Volume 6. In Press. See also, Duchamp, D. J.; Marsh, R. E. Acta. Cryst. 1969, B25, 5.
15. Yang, J.; Marendaz, J. L.; Geib, S. J.; Hamilton, A. D, Tetrahedron Lett. 1994, 3665.
16. For a related approach see; Valiyaveeteil, S.; Erkelmann, V.; Müllen, K. J. Chem. Soc. Chem. Commun. 1994, 2097.
17. Yang, J.; Zafar, A.; Marendez, J.-L.; Geib, S. J.; Hamilton, A. D. in Supramolecular Stereochemistry, Siegel, J. S. Ed.; Kluwer: Dordrecht, 1995, pp 141-146.
18. 3.
19. Fan, E.; Hamilton, A.D.; van Arman, S. J. Am. Chem. Soc. 1993, 115, 369.
20. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.
21. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.
22. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.
23. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.
24. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.
25. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.
26. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.
27. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.
28. For other studies on hydrogen bonded self-assembly in solution; Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215. Gallant, M.; Viet, M. T. P.; Wuest, J. D. J. Org. Chem. 1991, 56, 2284. Wyler, R.; de Mendoza, J.; Rebek, J. Jr., Angew. Chem. Int. Ed. 1993, 32, 1699. Mathias, J. P.; Simanek, E. E.; Seto, C. T.; Whitesides, G. M. Angew. Chem. Int. Ed. 1993, 32, 1766. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1993, 1677. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330. Bonazzi, S.; DeMorais, M. M.; Gottarelli, G.; Mariani, P.; Spada, G. P. Angew. Chem. Int. Ed. 1993, 32, 248. Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1993, 243.