Self-organization of four symmetric tri-phenyl-benzene derivatives

Crystal Growth and Design

Volumn 6, Issue 11, 2006, Pages 2486-2492

  Vergadou, Vassiliki ^a   Pistolis, George ^b   Michaelides, Adonis ^a   Varvounis, George ^a   Siskos, Michael ^a   Boukos, Nikos ^b   Skoulika, Stavroula ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

^b INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751270203     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg060183m     Document Type: Article

References (50)

1. (a) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
2. (b) Fujita, M., Ed.; Molecular Self-Assembly; Structure and Bonding Vol. 96; Springer: Berlin, 2000.
3. (c) Desiraju, G. R., Ed.; The Crystal as a Supramolecular Entity; Perspectives in Supramolecular Chemistry Vol. 2; Wiley: Chichester, U.K., 1995.
4. (d) Hollingsworth, M. D. Science 2002, 295, 2410.
5. (e) Whitesides, G. M.; Grzybowski, B. Science 2002, 295, 2418.
6. (f) Rogers, R. D., Zaworotko M. J., Eds.; Crystal Engineering. In Proceedings of the ACA Transactions Symposium, Arlington, VA, July 18-23, 1998; American Crystallographic Association: Buffalo, NY, 1998; Vol. 33.
7. (a) Gavezzotti, A. Acc. Chem. Res. 1994, 27, 309.
8. (b) Gavezzotti, A., Ed.; Theoretical Aspects and Computer Modeling of the Molecular Solid State; Wiley & Sons: New York, 1997.
9. (c) Lommerse, J. P. M.; Motherwell, W. D. S.; Ammon, H. L.; Dunits, J. D.; Gavezzotti, A.; Hofmann, D. W. M.; Leusen, F. J. J.; Mooij, W. T. M.; Price, S. L.; Schweizer, B.; Scmidt, M. V.; Van Eijck, B. P.; Verwer, P.; Williams, D. E. Acta Crystallogr., Sect. B 2000, 56, 697.
10. Holman, K. T.; Pivovar, A. M.; Ward, M. D. Science 2001, 294, 1907.
11. (b) Thalladi, V. R.; Brasselet, S.; Blaser, D.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. Chem. Commun. 1997, 1841.
12. (c) Frankenbach, G. M.; Etter, M. C. Chem. Mater. 1992, 4, 272.
13. Fernandez-Lopez, S.; Kim, H. S.; Choi, E. C.; Delgado, M.; Granja, J. R.; Khasanov, A.; Kraehenbuehl, K.; Long, G. Nature 2001, 412, 452.
14. (a) Brunet, P.; Simard, M.; Wust, J. D. J. Am. Chem. Soc. 1997, 119, 2737.
15. (b) Russel, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575.
16. (c) Endo, K.; Sawaki, T.; Koyanagi, M.; Kobayashi, K.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1995, 117, 8341.
17. VanDelden, R. A.; Koumura, N.; Harada, N.; Feringa, B. N. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4945.
18. Lydon, J. Curr. Opin. Colloid Interface Sci. 1998, 3, 458.
19. (a) Etter, M. C. J. Phys. Chem. 1991, 95, 4601.
20. (b) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747.
21. (c) Ermer, O.; Eling, A. J. Chem. Soc., Perkin Trans. 2 1994, 925.
22. Sharma, C. V.; Panneerelvam, K.; Pilati, T.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1994, 2209.
23. Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3440.
24. White, D. J.; Cronin, L.; Parsons, S.; Robertson, N.; Tasker, P. A.; Bisson, A. P. Chem. Commun. 1999, 1107.
25. The crystal structure of the analogous compound with X = OH has been determined previously by Desiraju et al. (Chem. Commun. 2002, 344). In this case, a closely packed layered structure is obtained by the formation of an unusual seven-memberd chain of hydrogen bonds in which OH acts as both hydrogen bond donor and acceptor. This type of packing, in which all available strong and weak donors and acceptors are optimized, follows from the conformational properties of the OH group and the conformational flexibility of the molecule.
26. Lin, Y. C.; Williams, D. E. Acta Crystallogr., Sect. B 1975, 31, 318.
27. Weber, E.; Hecker, M.; Koepp, E.; Orlia, W.; Czugler, M.; Csoregh, I. J. Chem. Soc., Perkin Trans. 2 1988, 1251.
28. a) Duchamp, D. J.; Marsh, R. E. Acta Crystallogr., Sect. B 1969, 25, 5.
29. (b) Herbstein, F. H.; Kapon, M.; Shteiman, V. Acta Crystallogr., Sect. B 2001, 57, 692.
30. (c) Herbstein, F. H.; Marsch, R. E. Acta Crystallogr., Sect. B 1977, 33, 2358.
31. The geometrical criterion cited in Lowry T. H.; Richardson., K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Addison-Wesley: Boston, 1997, for excimer formation via π-π interactions of aromatic rings is an interplanar angle near 0° and an interplanar distance less than 3.5 Å. Extended aromatic systems interact more strongly than isolated ones.
32. See also: Chen, M.; Ghiggino, K. P.; Smith, T. A.; Thang, S. H.; Wilson, G. J. Austr. J. Chem. 2004, 57, 1175.
33. Young, H. K.; Beckerbauer, R. Macromolecules 1994, 27, 1968.
34. Beltran, L. M. C.; Cui, C.; Leung, D. H.; Xu, J.; Hollander, F. J. Acta Crystallogr., Sect. E 2002, 58, 782.
35. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
36. Walborsky, H. M.; Barash, L.; Young, A. E.; Impastato, F. J. J. Am. Chem. Soc. 1961, 83, 2517.
37. Silverstein, R. S. M.; Bassler, G. C.; Morill, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley & Sons: New York, 1991.
38. (a) Lu, R.; Jiang, Y. S.; Duo, J. Q.; Chai, X. D.; Yang, W. S.; Lu, N.; Cao, Y. W.; Li, T. J. Supramol. Sci. 1998, 5, 737.
39. (b) Sielcken, O. E.; Van Tilborg, M. M.; Roks, M. F. M.; Hendriks, R.; Drenth, W.; Nolte, R. J. M. J. Am. Chem. Soc. 1987, 109, 4261.
40. (c) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, T. J. Am. Chem. Soc. 1995, 117, 7. 6360.
41. (d) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 9, 499.
42. (e) Marguet, S.; Markovitsi, D.; Millie, P.; Sigal, H.; Kumar, S. J. Phys. Chem. B 1998, 102, 4697.
43. (a) Winnik, F. M. Chem. Rev. 1993, 93, 587.
44. (b) Silva, A. P.; Gunarathe, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher J. T.; Rice. T. E. Chem. Rev. 1997, 97, 1515.
45. (c) Yamazaki, I.; Winnik, F. M.; Winnik, M. A.; Tazuke, S. J. Phys. Chem. 1987, 91, 4213.
46. (d) Tsujii, Y.; Itoh, T.; Fukuda, T.; Miyamoto, T.; Ito S.; Yamamoto, M. Langmuir 1992, 8, 936.
47. (e) Pistolis, G. Chem. Phys. Lett. 1999, 304, 371.
48. (f) Itaya, A.; Okamoto, K.; Kusabayashi, S. Bull. Chem. Soc. Jpn. 1976, 49, 2082.
49. (a) Mizuno K.; Matsui, A. J. Lumin. 1987, 38, 323.
50. (b) Sumi. H. Chem. Phys. 1989, 130, 433.