Asymmetric Discotic Liquid Crystals Based on Rufigallol

Chemistry of Materials

Volumn 9, Issue 7, 1997, Pages 1630-1637

  Raja, K S ^a   Ramakrishnan, S ^a   Raghunathan, V A ^b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b RAMAN RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001691569     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm970019+     Document Type: Article

References (38)

1. Chandrasekhar, S. Liquid Crys. 1993, 14, 3.
2. Fontes, E.; Heiney, P. A. Phys. Rev. A 1988, 37, 1329.
3. Collard, D. M.; Lillya, C. P. J. Am. Chem. Soc. 1989, 111, 1829.
4. (a) Kardan, M.; Reinhold, B. B.; Hsu, S. L.; Thakur, R.; Lillya, C. P. Macromolecules 1986, 19, 616.
5. (b) Yang, X.; Kardan, M.; Hsu, S. L.; Collard, D. M.; Heath, R. B.; Lillya, C. P. J. Phys. Chem. 1988, 92, 196.
6. (c) Yang, X.; Waldman, D. A.; Hsu, S. L.; Nitzsche, S. A.; Thakur, R.; Collard, D. M.; Lillya, C. P.; Stidham, H. D. J. Chem. Phys. 1988, 89, 5950.
7. (5) For examples see: Chandrasekhar, S. Advances in Liquid Crystals; Brown G. H., Ed., Academic Press: New York, 1982; Vol. 5. Demus, A. Liquid Cryst. 1989, 5, 75.
8. For examples see: Chandrasekhar, S. Advances in Liquid Crystals; Brown G. H., Ed., Academic Press: New York, 1982; Vol. 5. Demus, A. Liquid Cryst. 1989, 5, 75.
9. Schouten, P. G.; van der Pol, J. F.; Zwikker, J. W.; Drenth, W.; Picken, S. J. Mol. Cryst. Liq. Cryst. 1991, 195, 291.
10. Collard, D. M.; Lillya, C. P. J. Am. Chem. Soc. 1991, 113, 8577
11. Collard, D. M.; Lillya, C. P. J. Org. Chem. 1991, 56, 6064.
12. Lillya, C. P.; Collard D. M. Mol. Cryst. Liq. Cryst. 1990, 182B, 201.
13. Tabushi, I.; Yamamura, K.; Okada, Y. J. Org. Chem. 1987, 52, 2502.
14. Mullen, K.; Goltner, C.; Pressner, D.; Spiess, H. W. Angew Chem. Int. Ed. Engl. 1993, 32, 1660.
15. Tinh, N. H.; Bernaud, M. C.; Sigaud, G.; Destrade, C. Mol. Cryst. Liq. Cryst. 1981, 65, 307.
16. Boden, N.; Bushby, R. J.; Cammidge, A. N. J. Chem. Soc., Chem. Commun. 1994, 465.
17. Boden, N.; Bushby, R. J.; Cammidge, A. N. J. Am. Chem. Soc. 1995, 117, 924.
18. Grimshaw, J.; Hawarth, R. D. J. Chem. Soc. 1956, 56, 4225.
19. 15 who isolated it by treating rufigallol with excess ethereal diazomethane in order to establish the structure of rufigallol.
20. 21
21. Carfagna, C.; Ianneli, P.; Roviollo, A.; Sirigu, A. Liquid Cryst. 1987, 2, 611.
22. 18 that report the same compound as being enantiotropic with a mesophase range of about 24°C.
23. No explanation for this behavior is possible without further data points with larger values of n.
24. Raja K. S.; Ramakrishnan, S., unpublished results.
25. A similar sharp increase in was also reported for the symmetric hexaalkanoates of rufigallol by Carfagna et al.: Carfagna, C.; Roviello, A.; Sirigu, A. Mol. Cryst. Liq. Cryst. 1985, 122, 151.
26. (a) Kaufman, H. S.; Sacher, A.; Alfrey, T.; Frakuchen, I. J. Am. Chem. Soc. 1948, 76, 6280.
27. (b) Jordan, E. F., Jr.; Feldeisen, D. W.; Wrigley, A. N. J. Polym. Sci., Part A-1 1971, 9, 1835.
28. (c) Jordan, E. F., Jr.; Artymyshyn, B.; Speca, A.; Wrigley, A. N. J. Polym. Sci., Part A-1 1971, 9, 3349.
29. (d) Plate, N. A.; Shibaev, V. P. J. Polym. Sci., Macromol. Rev. 1974, 8, 117.
30. (e) Hsieh, H. W. S.; Post, B.; Morawetz, H. J. Polym. Sci., Polym. Phys. Ed. 1976, 14, 1241.
31. (a) Watanabe, J.; Ono, H.; Uematsu, I.; Abe, A. Macromolecules 1985, 18, 2141.
32. (b) Watanabe, J.; Ono, H.; Macromolecules 1986, 19, 1079.
33. 28
34. 25 appears to suggest that in these systems the alkyl chain carbon atoms close to the aromatic core may, in fact, be more conformationally restricted in the discotic phase than in the isotropic phase and hence also contribute to the observed change in entropy, ΔSi. This would also explain its rather steep dependence at smaller values of n and a tapering off at higher values (see Figure 9).
35. Destrade, C.; Malthete, M. C.; Tinh, N. H. J. Phys. (Paris) 1979, 40, 3.
36. Chandrasekhar, S.; Sadashiva, B. K.; Suresh, K. A. Pramana, 1977, 9, 471.
37. Value obtained using the Insight molecular modeling package.
38. Small, D. M. Physical Chemistry of Lipids; Plenum: New York, 1986.