Hostname: page-component-cd9895bd7-q99xh Total loading time: 0 Render date: 2024-12-27T02:34:17.551Z Has data issue: false hasContentIssue false
  • English
  • Français

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

Published online by Cambridge University Press:  10 February 2011

H.-J. Deussen ,
P. V. Shibaev ,
R. A. Vinokur ,
K. Schaumburg ,
T. Bjornholm ,
K. Bechgaard  and
V. P. Shibaev
H.-J. Deussen
Affiliation:
CISMI, Department of Chemistry, University of Copenhagen, SYMBION Science Park, Fruebjergvej 3, DK-2100, Copenhagen ø, Denmark
P. V. Shibaev
Affiliation:
Moscow State University, Physical and Chemical Departments, 119899 Moscow, Russia
R. A. Vinokur
Affiliation:
Moscow State University, Physical and Chemical Departments, 119899 Moscow, Russia
K. Schaumburg
Affiliation:
CISMI, Department of Chemistry, University of Copenhagen, SYMBION Science Park, Fruebjergvej 3, DK-2100, Copenhagen ø, Denmark
T. Bjornholm
Affiliation:
CISMI, Department of Chemistry, University of Copenhagen, SYMBION Science Park, Fruebjergvej 3, DK-2100, Copenhagen ø, Denmark
K. Bechgaard
Affiliation:
RISø, Department of Solid States Phyiscs, DK-4000 Roskilde, Denmark
V. P. Shibaev
Affiliation:
Moscow State University, Physical and Chemical Departments, 119899 Moscow, Russia
Get access

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

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 425: Symposium I – Liquid Crystals for Advanced Technologies , 1996 , 55
Copyright
Copyright © Materials Research Society 1996

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

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).Google Scholar
2. Bhatt, J.C., Keast, S.S., Neubert, M.E., Petschek, R.C., Liq. Crystals 18, 367 (1995).Google Scholar
3. Suchod, B., Renault, A., Lajzerowicz, J., Spada, G.P., J. Chem. Soc. Perkin Trans. II, 1839 (1992).Google Scholar
4. Gottarelli, G., Hibert, M., Samori, B., Solladie, G., Spada, G.P., Zimmermann, R., J. Am. Chem. Soc. 105, 7318 (1983).Google Scholar
5. Gottarelli, G., Spada, G.P., J. Org. Chem. 51 (5), 589 (1986).Google Scholar
6. Gottarelli, G., Spada, G. P., Mol. Cryst. Liq. Cryst. 123, 377 (1985).Google Scholar
7. Kelly, S. M., Schadt, M., Seiberle, H., Liq. Crystals 11 (5), 761 (1992).Google Scholar
8. Zhang, M., Shuster, G., J. Am. Chem. Soc. 116, 4852 (1994).Google Scholar
9. Kuroda, R., Mason, S.F, J. Chem. Soc. Perkin Trans. II, 167; 870 (1981).Google Scholar
10. Thorup, N., Deussen, H.-J., Bjornholm, T., Bechgaard, K., ECM 16 Lund, 16th European Crystallografic Meeting 6–11 August 1995, Lund, Sweden.Google Scholar
11. Tsuzuki, S., Tanabe, K., Nagawa, Y., Nakanishi, H., J. Mol. Struct. 216, 279 (1990).Google Scholar
12. Kranz, M., Clark, T., von Rague Schleyer, P., J. Org. Chem. 58, 3317 (1993).Google Scholar
13. Baraldi, I., Bruni, M.C., Caselli, M., Ponterini, G., J.Chem.Soc.Faraday Trans. II 85 (1), 65 (1989).Google Scholar
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).Google Scholar
15. Candau, S., le Roy, P., Debeauvais, F., Mol. Cryst. Liq. Cryst. 23, 283 (1973).Google Scholar
16. Grandjean, F.C.R., Ackad. Sci., 172 (1921).Google Scholar
17. Kano, R., Bull. Soc. Fr. Min. Cryst. 91, 20 (1968).Google Scholar
18. Heppke, G., Oestreicher, F.,Naturforsch, Z.., Teil A, 32, 899 (1977).Google Scholar