Diastereomer liquid crystalline CF3 molecules: conformational probe for (anti)ferroelectricity and spontaneous resolution of the racemates

Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals

Volumn 346, Issue , 2000, Pages 41-49

  Mikami, Koichi ^a   Yajima, Tomoko ^a   Kojima, Jun ^a   Terada, Masahiro ^a   Kawauchi, Susumu ^a   Shirasaki, Hiroko ^b   Okuyama, Kenji ^b   Suzuki, Yoshiichi ^c   Kobayashi, Ichiro ^c   Takanishi, Yoichi ^a   Takezoe, Hideo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^c Central Research and Development Laboratory   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFERROELECTRICITY; CONFORMATIONS; ELECTROOPTICAL EFFECTS; ISOMERS; MOLECULAR STRUCTURE; MOLECULES;

DIASTEREOMERS; DOUBLE STEREOGENIC CENTERS; ELECTROOPTIC SWITCHING;

LIQUID CRYSTALS;

EID: 0034476755     PISSN: 1058725X     EISSN: None     Source Type: Journal    
DOI: 10.1080/10587250008023864     Document Type: Article

References (26)

1. Miyachi, et al., Handbook of Liquid Crystals, Vol. 2B, Wiley-VCH, p. 664 (1998). Also see the first reports: (a) N. Hiji, A. D. L. Chandani, S. Nishiyama, Y. Ouchi, H. Takezoe, A. Fukuda, Ferroelectrics, 85, 99 (1988).
2. Miyachi, et al., Handbook of Liquid Crystals, Vol. 2B, Wiley-VCH, p. 664 (1998). Also see the first reports: (a) N. Hiji, A. D. L. Chandani, S. Nishiyama, Y. Ouchi, H. Takezoe, A. Fukuda, Ferroelectrics, 85, 99 (1988).
3. (b) A. D. L. Chandani, T. Hagiwara, Y. Suzuki, Y. Ouchi, H. Takezoe, A. Fukuda, Jpn. J. Appl. Phys., 27, L729 (1988).
4. c) Y. Suzuki, T. Hagiwara, I. Kawamura, N. Okamura, T. Kitazume, M. Kakimoto, Y. Imai, Y. Ouchi, H. Takezoe, A. Fukuda, Liq. Cryst., 6, 167 (1989).
5. d) K. Furukawa, K. Terashima, M. Ichihashi, S. Saitoh, K. Miyazawa, T. Inukai, Ferroelectrics, 85, 451 (1988).
6. (e) A. D. L. Chandani, E. Gorecka, Y. Ouchi, H. Takezoe, A. Fukuda, Jpn, J. Appl. Phys., 28, L1265 (1989).
7. (a) J. Watanabe, M. Hayashi, Macromolecules, 22, 4083 (1989).
8. (b) J. Watanabe, S. Kinoshita, J. Phys. II (France), 2, 1237 (1992).
9. X-ray crystal analysis of bent conformations of AFLC molecules: (a) K. Hori, K. Endo, Bull. Chem. Soc. Jpn., 66, 46 (1993).
10. (b) K. Hori, S. Kawahara, K. Ito, Ferroelectrics, 147, 91 (1994).
11. c) K. Okuyama, N. Kawano, S. Uehori, K. Noguchi, N. Okabe, Y. Suzuki, I. Kawamura, Mol. Cryst. Liq. Cryst., 276, 193 (1996).
12. (a) K. Mikami, T. Yajima, N. Siree, M. Terada, Y. Suzuki, I. Kobayashi, Abstr., 3H218 in the 69th Annual Meeting of the Chemical Society of Japan, Kyoto, March, 1995.
13. (b) K. Mikami, T. Yajima, N. Siree, M. Terada, Y. Suzuki, I. Kobayashi, Synlett, 1996, 837.
14. c) K. Mikami, T. Yajima, M. Terada, S. Kawauchi, Y. Suzuki, I. Kobayashi, Chem. Lett., 1996, 861.
15. d) I. Kobayashi, Y. Suzuki, T. Yajima, S. Kawauchi, M. Terada, K. Mikami, Mol. Cryst. Liq. Cryst., 303, 165 (1997).
16. (a) K. Mikami, T. Yajima in EPC Synthesis of Fluoro-Organic Compounds, V. A. Soloshonok, Ed., John Willy & Sons, Inc., p. 557 (1999).
17. (b) K. Mikami, T. Yajima, T. Takasaki, S. Matsukawa, M. Terada, T. Uchimaru, M. Maruta, Tetrahedron, 52, 85 (1996).
18. c) K. Mikami, T. Yajima, M. Terada, E. Kato, M. Maruta, Tetrahedron Asymm., 5, 1087 (1994).
19. d) K. Mikami, T. Yajima, M. Terada, T. Uchimaru, Tetrahedron Lett., 34, 7591 (1993).
20. Quite recently, Prof. Fukuda has determined that the chiral alkyl chain makes a bent angle >54.7° (the magic angle) with the core axis and that the carbonyl group near the chiral center lies on the tilt plane in antiferroelectric SmCA* on the basis of the polarized infrared spectroscopy. B. Jin, Z. Ling, Y. Takanishi, K.Ishikawa, H. Takezoe, A. Fukuda, M. Kakimoto, T. Kitazume, Phys Rev., E53, R4295 (1996).
21. K. Mikami, T. Yajima, M. Terada, Y. Suzuki, I. Kobayashi, J. Chem. Soc., Chem. Commun., 1997, 57.
22. Review: J. Jacques, A. Collet, S. H. Wilen, Enantiomers. Racemates and Resolutions, J. Wiley & Sons, New York (1981).
23. C. J. Chardt, N. M. Peachy, D. R. Swanson, J. M. Takacs, M. A. Khan, X. Gong, J.-H. Kim, J. Wang, R. A. Uphaus, Nature, 362, 614 (1993).
24. F. Stevens, D. J. Dyer, D. M. Walba, Angew. Chem. Int. Ed. Engl., 35, 900 (1996).
25. D. R. Link, G. Natale, R. Shao, J. E. Maclennan, N. A. Clark, E. Korblova, D. M. Walba, Science, 278, 1924 (1997).
26. Y. Takanishi, H. Takezoe, Y. Suzuki, I. Kobayashi, T. Yajima, M. Terada, K. Mikami, Angew. Chem. Int. Ed., in press.