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Synthesis of New Chiral Disubstituted Binaphthol Derivatives and their use as the Chiral Dopants

  • H.-J. Deussen (a1), P. V. Shibaev (a2), R. A. Vinokur (a2), K. Schaumburg (a1), T. Bjornholm (a1), K. Bechgaard (a3) and V. P. Shibaev (a2)...

Abstract

A number of new chiral binaphthol (BN) derivatives with different substituents in the 6,6'-positions in open and bridged forms have been synthesized. Their possible liquid crystalline properties and their helical twisting power (B) of three different nematic liquid crystals (LCs) were investigated. Derivatives with spatially extended substituents in the 6,6'-positions (e.g. styryl or vinil) show unusual high helical twisting power (up to 120 μm–1). A direct correlation between the magnitude of β and the length of the substituents was found.

From the different temperature dependence of β of the open and bridged BNs, a molecular model was developed relating the molecular conformation and twisting power

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1. Goodby, J.W., Slaney, A.J., Booth, C.J., Nishiyama, I., Vuijk, J.D., Styring, P., Toyne, K., Mol. Cryst. Liq. Cryst. 243, 231 (1994).
2. Bhatt, J.C., Keast, S.S., Neubert, M.E., Petschek, R.C., Liq. Crystals 18, 367 (1995).
3. Suchod, B., Renault, A., Lajzerowicz, J., Spada, G.P., J. Chem. Soc. Perkin Trans. II, 1839 (1992).
4. Gottarelli, G., Hibert, M., Samori, B., Solladie, G., Spada, G.P., Zimmermann, R., J. Am. Chem. Soc. 105, 7318 (1983).
5. Gottarelli, G., Spada, G.P., J. Org. Chem. 51 (5), 589 (1986).
6. Gottarelli, G., Spada, G. P., Mol. Cryst. Liq. Cryst. 123, 377 (1985).
7. Kelly, S. M., Schadt, M., Seiberle, H., Liq. Crystals 11 (5), 761 (1992).
8. Zhang, M., Shuster, G., J. Am. Chem. Soc. 116, 4852 (1994).
9. Kuroda, R., Mason, S.F, J. Chem. Soc. Perkin Trans. II, 167; 870 (1981).
10. Thorup, N., Deussen, H.-J., Bjornholm, T., Bechgaard, K., ECM 16 Lund, 16th European Crystallografic Meeting 611 August 1995, Lund, Sweden.
11. Tsuzuki, S., Tanabe, K., Nagawa, Y., Nakanishi, H., J. Mol. Struct. 216, 279 (1990).
12. Kranz, M., Clark, T., von Rague Schleyer, P., J. Org. Chem. 58, 3317 (1993).
13. Baraldi, I., Bruni, M.C., Caselli, M., Ponterini, G., J.Chem.Soc.Faraday Trans. II 85 (1), 65 (1989).
14. Deussen, H.-J., Shibaev, P.V., Vinokur, R.A., Schaumburg, K., Bjomholm, T., Bechgaard, K., Shibaev, V.P., New 6,6'-Disubstituted-Binaphthol Derivatives as Chiral Dopants. Synthesis and Temperature Dependence of Molecular Conformations (submitted for publication in Liq. Crystals).
15. Candau, S., le Roy, P., Debeauvais, F., Mol. Cryst. Liq. Cryst. 23, 283 (1973).
16. Grandjean, F.C.R., Ackad. Sci., 172 (1921).
17. Kano, R., Bull. Soc. Fr. Min. Cryst. 91, 20 (1968).
18. Heppke, G., Oestreicher, F.,Naturforsch, Z.., Teil A, 32, 899 (1977).

Synthesis of New Chiral Disubstituted Binaphthol Derivatives and their use as the Chiral Dopants

  • H.-J. Deussen (a1), P. V. Shibaev (a2), R. A. Vinokur (a2), K. Schaumburg (a1), T. Bjornholm (a1), K. Bechgaard (a3) and V. P. Shibaev (a2)...

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