An assessment of carborane-containing liquid crystals for potential device application

(Note: The full text of this document is currently only available in the PDF Version )

Andrew G. Douglass, Krzysztof Czuprynski, Michelle Mierzwa and Piotr Kaszynski


Abstract

Two 4-alkoxyphenyl 12-pentylcarborane-1-carboxylate nematic liquid crystals have been synthesized. The materials are found to exhibit ideal mixing of nematic phases in their binary mixtures with analogous bicyclo[2.2.2]octane derivatives and with the polar nematogen 4-(4-isothiocyanatophenyl)-1-(trans-hexyl)cyclohexane. The smectic phases for the bicyclo[2.2.2]octanes are destabilized by addition of the carborane derivative. For carborane compound 5BC5 the extrapolated dielectric anisotropy and measured optical anisotropy are 1.3 and 0.057 respectively at 20°C. The refractive indices have been correlated with the calculated electronic polarizabilities and the low birefringence measured for 5BC5 can, at least in part, be attributed to the carborane cylindrical symmetry.


References

  1. I. Sage, in Thermotropic Liquid Crystals, ed. G. W. Gray, John Wiley and Sons, 1987, pp. 64–98 Search PubMed.
  2. D. Coates, in Thermotropic Liquid Crystals, ed. G. W. Gray, John Wiley & Sons, New York, 1987, pp. 99–119 Search PubMed.
  3. D. Demus, Mol. Cryst. Liq. Cryst., 1988, 165, 45 CAS.
  4. K. J. Toyne, in Thermotropic Liquid Crystals, ed. G. W. Gray, John Wiley and Sons, New York, 1987, pp. 28–63 Search PubMed.
  5. Boron Hydride Chemistry, ed. E. L. Muetterties, Academic Press, New York, 1975 Search PubMed.
  6. A. G. Douglass, M. Mierzwa and P. Kaszynski, SPIE, 1998, 3319, 59 Search PubMed.
  7. P. Kaszynski and D. Lipiak, in Materials for Optical Limiting, ed. R. Crane, K. Lewis, E. V. Stryland and M. Khoshnevisan, MRS, 1995, 374, 341 Search PubMed.
  8. P. Kaszynski, J. Huang, G. S. Jenkins, K. A. Bairamov and D. Lipiak, Mol. Cryst. Liq. Cryst., 1995, 260, 315 Search PubMed.
  9. K. Czuprynski, A. G. Douglass, P. Kaszynski and W. Drzewinski, Liq. Cryst., submitted Search PubMed.
  10. P. Kaszynski and K. Czuprynski, Chem. Commun., submitted Search PubMed.
  11. A. G. Douglass, K. Czuprynski, M. Mierzwa and P. Kaszynski, Chem. Mater., in press Search PubMed.
  12. R. B. King, Russ. Chem. Bull., 1993, 42, 1283 CrossRef.
  13. V. I. Bregadze, Chem. Rev., 1992, 92, 209 CrossRef CAS and references therein.
  14. R. N. Grimes, Carboranes, Academic Press, New York, 1970 Search PubMed.
  15. G. W. Gray and S. M. Kelly, Mol. Cryst. Liq. Cryst., 1981, 75, 95 CAS.
  16. R. Dabrowski, J. Dziaduszek, T. Szczucinski and Z. Raszewski, Mol. Cryst. Liq. Cryst., 1984, 107, 411 CAS.
  17. V. V. Korshak, N. I. Bekasova, A. I. Solomatina, T. M. Frunze, A. A. Sakharova and O. A. Mel'nik, Izv. Akad. Nauk. SSSR, Ser. Khim., 1982, 31, 1904 Search PubMed.
  18. P. Adomenas, A. Nenishkis and D. Girdzhyunaite, J. Org. Chem. USSR, 1982, 18, 1100.
  19. R. Dabrowski, J. Szulc and B. Sosnowska, Mol. Cryst. Liq. Cryst., 1992, 215, 13 Search PubMed.
  20. J. Przedmojski, personal communication.
  21. The more commonly used reduced temperature scale (T/TNI in K) gives similar results.
  22. I. H. Ibrahim and W. Haase, J. Phys. (Paris), 1979, 40, 191 Search PubMed Data not available for 5PH5.
  23. M. Takahashi, S. Mita and S. Kondo, Mol. Cryst. Liq. Cryst., 1986, 132, 53 CAS.
  24. M. F. Vuks, Opt. Spectrosc. (Engl. Transl.), 1966, 20, 361 Search PubMed.
  25. The molar volume contribution for the carborane cage was estimated to be 126±9 cm3 mol–1 by statistical analysis of eight disubstituted o- and m-carborane compounds. To our knowledge no density data have been reported for disubstituted p-carboranes.
  26. The temperature dependence of the calculated molar volume for 5BO5 was assumed to be equal to that measured experimentally for 5CH5.
  27. R. F. Fedors, Polym. Eng. Sci., 1974, 14, 147 Search PubMed.
  28. P. Kromm, H. Allouchi, J.-P. Bideau, M. Cotrait and H. T. Nguyen, Acta. Crystallogr., Sect. C, 1995, 51, 1229 CrossRef.
  29. U. Baumeister, W. Brandt, H. Hartung, W. Wedler, H.-J. Deutscher, R. Frach and M. Jaskolski, Mol. Cryst. Liq. Cryst., 1985, 130, 321 CAS.
  30. R. Martin, Monatsh. Chem., 1981, 112, 1155 CAS.
  31. V. Vill, Liq. Cryst. 3.0, Hamburg, 1997, compound #22714 Search PubMed.
  32. Experimental value for B12H122– has been measured as 22.0 Å3; A. Kaczmarczyk and G. B. Kolski, Inorg. Chem., 1965, 4, 665 Search PubMed ; calculated (MNDO) value is 18.8 Å3. Similarly for p-carborane the calculated value is 18.7 Å3 and for benzene 10.2 Å3(exptl. 10.4 Å3).
  33. A. Saupe and W. Maier, Z. Naturforsch., Teil A, 1961, 16, 816.
  34. K. Toriyama, K. Suzuki, T. Nakagomi, T. Ishibashi and K. Odawara, in The Physics and Chemistry of Liquid Crystal Devices, ed. G. Sprokel, Plenum, New York, 1976, pp. 153–171 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.