Optically active poly(aryl carbonates) consisting of axially chiral units. Chiral binaphthyl group induced helical polymer

Journal of the American Chemical Society

Volumn 120, Issue 18, 1998, Pages 4530-4531

  Takata, Toshikazu ^a   Furusho, Yoshio ^a   Murakawa, Ken Ichi ^a   Endo, Takeshi ^b   Matsuoka, Hideo ^b   Hirasa, Takashi ^b   Matsuo, Jyuho ^b   Sisido, Masahiko ^c  

^a Osaka Prefecture University   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000850453     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja974337l     Document Type: Letter

References (33)

1. Seimitsu Jyugo (Controlled Polymerization) (Japan); Kagaku Sosetsu No. 18; Chem. Soc. Jpn. Ed.; Gakkai Shuppan Center: Tokyo, 1993.
2. For reviews, see: (a) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349.
3. (b) Okamoto, Y.; Yashima, E. Prog. Polym. Sci. 1990, 15, 263.
4. (c) Wulff, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 21.
5. (d) Optically Active Polymers; Selegny, E., Ed.; Reidel: Dordrecht, 1979.
6. For examples, see: (a) Kanoh, S.; Kawaguchi, N.; Suda, H. Makromol. Chem. 1987, 188, 463.
7. (b) Suda, H.; Kanoh, S.; Murose, N.; Goka, S.; Motoi, M. Polym. Bull. 1983, 10, 162.
8. (c) Sépulchre, M.; Spassky, N.; Mark, C.; Schurig, V. Makromol. Chem., Rapid Commun. 1981, 2, 261.
9. Takata, T.; Matsuoka, H.; Endo, T. Chem. Lett. 1991, 2091.
10. (a) Takata, T.; Sanda, F.; Ariga, T.; Nemoto, H.; Endo, T. Macromol. Rapid Commun. 1997, 18, 461.
11. (b) Ariga, T.; Takata, T.; Endo, T. Macromolecules 1997, 30, 737 and references therein.
12. (c) Takata, T.; Endo, T. Prog. Polym. Sci. 1993, 18, 839 and references therein.
13. Part of this work has been presented at the 41st Annual Meeting of Polymer Society of Japan; Morioka, Japan, 1992; Abstr. 29Pa-31.
14. Huang, W.-S.; Hu, Q.-S.; Zheng, X.-F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313 and references therein.
15. For examples, see: (a) Shibaev, V. P.; Deussen, H. J.; Bobrovsky, A. Yu.; Shibaev, P. V.; Boiko, N. I.; Bjornholm, T.; Schaumburg, K.; Bechgaard, K. Liq. Cryst. 1997, 22, 451.
16. (b) Bhowmik, P. K.; Atkins, E. D. T.; Lenz, R. W.; Han, H. Macromolecules 1996, 29, 1910.
17. (c) Gao, J. P.; Wang, Z. Y. J. Polym. Sci., Part A: Polym. Chem. 1995, 33, 1627.
18. (d) Nakano, T.; Sogah, D. Y. J. Am. Chem. Soc. 1995, 117, 534.
19. (e) Liou, G. S.; Kakimoto, M.; Imai, Y. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 587.
20. (f) Kakuchi, T.; Aoki, K.; Haba, O.; Yokota, K. Polym. Bull. 1993, 31, 37.
21. -1.
22. -1).
23. 20 +51.7° (c 1.00, THF)) (unpublished data). The total energy of 8 was calculated by varying the four dihedral angles around the carbonate group from 5 to 180° with an interval of 5°. Dihedral angle between the two naphthalene rings was set at τ = 73°. Generally dihedral angle of binaphthyl system is ranging from 68 to 92°: Akimoto, H.; Yamada, S. Tetrahedron 1971, 27, 5999 and references therein. As a result, right-handed screw sense P was suggested for (S)-8, while left-handed screw sense M was for (R)-8.
24. Theoretical CD spectrum of the modified 8 was computed on the basis of similar exiton theory applied to the quinoxaline system: Sisido, M.; Ishikawa, Y.; Harada, M.; Ito, K. Macromolecules 1991, 24, 3999.
25. Ito, Y.; Ihara, E.; Murakami, M.; Sisido, M. Macromolecules 1992, 25, 6810.
26. Vogl, O.; Jaycox, G. D. Polymer 1987, 28, 2179 and references therein.
27. For examples, see: (a) Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am. Chem. Soc. 1996, 118, 9188.
28. (b) Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1554.
29. (c) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596.
30. (d) Mikami, M.; Shinkai, S. Chem. Lett. 1995, 603.
31. (e) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860.
32. Non-hydrogen-bonded self-assembly helical oligopeptide: Okabayashi, H.; Isemura, T.; Sakakibara, S. Biopolymers 1968, 6, 323 and references therein.
33. Nakano, T.; Okamoto, Y. In Seimitsu Jyugo (Controlled Polymerization); Kagaku Sosetsu, No. 18; Chem. Soc. Jpn. Ed.; Gakkai Shuppan Center: Tokyo, 1993; Chapter 10, p 129.