Asymmetric synthesis of helically stable poly(quinoxaline-2,3-diyl)s having hydrophilic and/or hydrophobic side chains

Macromolecules

Volumn 31, Issue 5, 1998, Pages 1697-1699

  Ito, Yoshihiko ^a   Miyake, Toshiyuki ^a   Ohara, Takafumi ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; INITIATORS (CHEMICAL); MOLECULAR STRUCTURE; MONOMERS; OPTICAL MATERIALS; POLYMERIZATION; PURIFICATION; SOLUBILITY; SPECTROSCOPIC ANALYSIS; SURFACE TREATMENT; SYNTHESIS (CHEMICAL);

CIRCULAR DICHROISM SPECTROSCOPY; HYDROPHILIC SIDE CHAIN; HYDROPHOBIC SIDE CHAIN; POLYQUINOXALINE;

AROMATIC POLYMERS;

EID: 0032021846     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9717855     Document Type: Article

References (25)

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3. For optically active poly(isocyanate)s without chiral substituents, see: Okamoto, Y.; Matsuda, M.; Nakano, T.; Yashima, B. Polym. J. 1993, 25, 391-396.
4. For optically active poly(isocyanide)s without chiral substituents, see: Nolte, R. J. M.; van Beijnen, A. J. M.; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932-5933. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818-0825. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926-7927. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1993, 115, 9101-9111.
5. For optically active poly(isocyanide)s without chiral substituents, see: Nolte, R. J. M.; van Beijnen, A. J. M.; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932-5933. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818-0825. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926-7927. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1993, 115, 9101-9111.
6. For optically active poly(isocyanide)s without chiral substituents, see: Nolte, R. J. M.; van Beijnen, A. J. M.; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932-5933. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818-0825. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926-7927. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1993, 115, 9101-9111.
7. For optically active poly(isocyanide)s without chiral substituents, see: Nolte, R. J. M.; van Beijnen, A. J. M.; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932-5933. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818-0825. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926-7927. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1993, 115, 9101-9111.
8. Chiral substituents at the side chains of the monomer can control and hold the screw sense of the helical polymer Poly(isocyanate)s: Goodman, M.; Chen, S.-C. Macromolecules 1970, 3, 398-402.
9. Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860-1866 and references therein.
10. Poly(isonitrile)s: Dorning, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 4400-4402.
11. Takei, F.; Yanai, K.; Onítsuka, K.; Takahashi, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1554-1556.
12. Poly(acetylene)s: Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-178.
13. Yashima, E.; Huang, S.; Matsushima, T.; Okamotn, Y. Macromolecules 1995, 28, 4184-4193 and references therein.
14. In contrast, optically active, helical conformation was induced by interaction of the achiral poly(acetylene)s with optically active compounds. Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800-9801.
15. (a) Ito, Y.; Ihara, M.; Murakami, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1509.
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18. (d) Ito, Y.; Kojima, Y.; Sugínome, M.; Murakami, M. Heterocycles 1996, 42, 597-615.
19. Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am. Chem. Soc. 1996,118, 9188-9189.
20. For the effect of the bulkiness of the 3,6-disubstituents on the stability of the screw sense, see: Ito, Y.; Kojima, Y.; Murakami, M.; Suginome, M. Bull. Chem. Soc. Jpn. 1997, 70, 2801-2806. See also ref 7.
21. 7 The CD spectra of these polymers were similar in shape, and their intensities at 362 nm were used for the determination of the selectivities. See Supporting Information.
22. n = 15 530 and 22 780), which were prepared independently by the polymerization of 60 and 80 equiv of 3 in the presence of 1d, respectively, showed the same CD intensity per quinoxaline unit.
23. The nearly complete screw-sense selection (>95% ee) was also attained in the polymerization of 2 (40 equiv) in the presence of 1d.
24. The mechanism of the induction of the high screw-sense selectivity will be discussed in a forthcoming paper.
25. a was also observed. The hypochromic solvent effect may be related to the observed decrease in the CD intensity of 7d in EtOH.