Synthesis and properties of polymers from disubstituted acetylenes with chiral pinanyl groups

Macromolecules

Volumn 32, Issue 1, 1999, Pages 79-85

  Aoki, Toshiki ^a   Kobayashi, Yukie ^a   Kaneko, Takashi ^a   Oikawa, Eizo ^a   Yamamura, Yasufumi ^b   Fujita, Yoji ^b   Teraguchi, Masahiro ^b   Nomura, Ryoji ^b   Masuda, Toshio ^b  

^a NIIGATA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; CATALYSTS; CONFORMATIONS; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; MOLYBDENUM COMPOUNDS; NIOBIUM COMPOUNDS; POLYMERIC MEMBRANES; POLYMERIZATION; SYNTHESIS (CHEMICAL); TANTALUM COMPOUNDS; THERMAL EFFECTS;

CIRCULAR DICHROISM;

POLYACETYLENES;

EID: 0032759785     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9810969     Document Type: Article

References (32)

1. For reviews of helical polymer syntheses, see: (a) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349-372. (b) Nolte, R. J. M. Chem. Soc. Rev. 1994, 11-19. (c) Qin, M.; Bartus, J.; Vogl, O. Macromol. Symp. 1995, 98, 387-402.
2. For reviews of helical polymer syntheses, see: (a) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349-372. (b) Nolte, R. J. M. Chem. Soc. Rev. 1994, 11-19. (c) Qin, M.; Bartus, J.; Vogl, O. Macromol. Symp. 1995, 98, 387-402.
3. For reviews of helical polymer syntheses, see: (a) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349-372. (b) Nolte, R. J. M. Chem. Soc. Rev. 1994, 11-19. (c) Qin, M.; Bartus, J.; Vogl, O. Macromol. Symp. 1995, 98, 387-402.
4. (a) Drenth, W.; Nolte, R. J. M. Acc. Chem. Res. 1979, 12, 30-35.
5. (b) Pu, L. Acta Polym. 1997, 48, 116-141.
6. For selected examples for chiral polyacetylenes, see: (a) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (b) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (c) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (d) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (e) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662-6666. (f) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
7. For selected examples for chiral polyacetylenes, see: (a) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (b) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (c) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (d) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (e) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662-6666. (f) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
8. For selected examples for chiral polyacetylenes, see: (a) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (b) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (c) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (d) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (e) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662-6666. (f) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
9. For selected examples for chiral polyacetylenes, see: (a) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (b) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (c) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (d) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (e) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662-6666. (f) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
10. For selected examples for chiral polyacetylenes, see: (a) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (b) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (c) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (d) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (e) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662-6666. (f) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
11. For selected examples for chiral polyacetylenes, see: (a) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (b) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (c) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (d) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (e) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662-6666. (f) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
12. For reviews of polymerization of acetylenic monomers, see: (a) Masuda, T. In Catalysis in Precision Polymerization; Kobayashi, S., Ed.; Wiley: Chichester, 1997; p 67. (b) Masuda, T. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 32. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups (supplement C2); Patai, S., Ed.; Wiley: Chichester, 1994; p 945. (d) Costa, G. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.; Pergamon Press: Oxford, 1989; p 155.
13. For reviews of polymerization of acetylenic monomers, see: (a) Masuda, T. In Catalysis in Precision Polymerization; Kobayashi, S., Ed.; Wiley: Chichester, 1997; p 67. (b) Masuda, T. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 32. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups (supplement C2); Patai, S., Ed.; Wiley: Chichester, 1994; p 945. (d) Costa, G. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.; Pergamon Press: Oxford, 1989; p 155.
14. For reviews of polymerization of acetylenic monomers, see: (a) Masuda, T. In Catalysis in Precision Polymerization; Kobayashi, S., Ed.; Wiley: Chichester, 1997; p 67. (b) Masuda, T. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 32. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups (supplement C2); Patai, S., Ed.; Wiley: Chichester, 1994; p 945. (d) Costa, G. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.; Pergamon Press: Oxford, 1989; p 155.
15. For reviews of polymerization of acetylenic monomers, see: (a) Masuda, T. In Catalysis in Precision Polymerization; Kobayashi, S., Ed.; Wiley: Chichester, 1997; p 67. (b) Masuda, T. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 32. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups (supplement C2); Patai, S., Ed.; Wiley: Chichester, 1994; p 945. (d) Costa, G. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.; Pergamon Press: Oxford, 1989; p 155.
16. (a) Masuda, T.; Deng, Y. X.; Higashimura, T. Bull. Chem. Soc. Jpn. 1983, 56, 2798-2801.
17. (b) Masuda, T.; Okano, Y.; Tamura, K.; Higashimura, T. Polymer 1985, 26, 793-793.
18. 3 eluent are not reproducible. A similar degradation also takes place in other solvents such as THF although the rate is low.
19. For reviews for gas-permeable polymer membranes, see: (a) Masuda, T.; Teraguchi, M.; Nomura, R. ACS Symp. Ser., in press. (b) Kesting, R. E.; Fritzsche, A. K. Polymeric Gas Separation Membranes; Wiley: New York, 1993. (c) Stern, S. A. J. Membr. Sci. 1994, 94, 1-65. (d) Cabasso, I. In Encyclopedia of Polymer Science and Engineering 1, 2nd ed.; Kroschwitz, J. I., Ed.; Wiley: New York, 1987; p 509. (e) Aoki, T.; Oikawa, E. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 6492.
20. For reviews for gas-permeable polymer membranes, see: (a) Masuda, T.; Teraguchi, M.; Nomura, R. ACS Symp. Ser., in press. (b) Kesting, R. E.; Fritzsche, A. K. Polymeric Gas Separation Membranes; Wiley: New York, 1993. (c) Stern, S. A. J. Membr. Sci. 1994, 94, 1-65. (d) Cabasso, I. In Encyclopedia of Polymer Science and Engineering 1, 2nd ed.; Kroschwitz, J. I., Ed.; Wiley: New York, 1987; p 509. (e) Aoki, T.; Oikawa, E. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 6492.
21. For reviews for gas-permeable polymer membranes, see: (a) Masuda, T.; Teraguchi, M.; Nomura, R. ACS Symp. Ser., in press. (b) Kesting, R. E.; Fritzsche, A. K. Polymeric Gas Separation Membranes; Wiley: New York, 1993. (c) Stern, S. A. J. Membr. Sci. 1994, 94, 1-65. (d) Cabasso, I. In Encyclopedia of Polymer Science and Engineering 1, 2nd ed.; Kroschwitz, J. I., Ed.; Wiley: New York, 1987; p 509. (e) Aoki, T.; Oikawa, E. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 6492.
22. For reviews for gas-permeable polymer membranes, see: (a) Masuda, T.; Teraguchi, M.; Nomura, R. ACS Symp. Ser., in press. (b) Kesting, R. E.; Fritzsche, A. K. Polymeric Gas Separation Membranes; Wiley: New York, 1993. (c) Stern, S. A. J. Membr. Sci. 1994, 94, 1-65. (d) Cabasso, I. In Encyclopedia of Polymer Science and Engineering 1, 2nd ed.; Kroschwitz, J. I., Ed.; Wiley: New York, 1987; p 509. (e) Aoki, T.; Oikawa, E. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 6492.
23. For reviews for gas-permeable polymer membranes, see: (a) Masuda, T.; Teraguchi, M.; Nomura, R. ACS Symp. Ser., in press. (b) Kesting, R. E.; Fritzsche, A. K. Polymeric Gas Separation Membranes; Wiley: New York, 1993. (c) Stern, S. A. J. Membr. Sci. 1994, 94, 1-65. (d) Cabasso, I. In Encyclopedia of Polymer Science and Engineering 1, 2nd ed.; Kroschwitz, J. I., Ed.; Wiley: New York, 1987; p 509. (e) Aoki, T.; Oikawa, E. In The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; p 6492.
24. Aoki, T.; Shinohara, K.; Kaneko, T.; Oikawa, E. Macromolecules 1996, 29, 4192-4198.
25. (a) Tsuchihara, K.; Masuda, T.; Higashimura, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 547-552.
26. (b) Tsuchihara, K.; Masuda, T.; Higashimura, T. Macromolecules 1992, 25, 5816-5820.
27. (c) Ito, H.; Masuda, T.; Higashimura, T. J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 2925-2929.
28. Izumikawa, H.; Masuda, T.; Higashimura, T. Polym. Bull. 1991, 27, 193-199.
29. The shape of CD spectrum of poly(1) significantly differs from that of poly(2), and the magnitude of [θ] of poly(2) around 380 nm was approximately 1.7 times as large as that of poly(1). On the other hand, the CD intensity of poly(1) around 300 nm was much larger than that of poly(2).
30. 1H NMR of 5 as shown below. Irradiation of the methyl protons (a) at 0.82 ppm caused an NOE enhancement of the signal attributable to the proton (b) at 2.19 ppm, whereas no NOE enhancement was detected for the methylene protons (c) at 0.52-0.69 ppm. (Chemical Equation Presented)
31. Chang, T. L.; Holzknecht, L. J.; Mark, J. H. B.; Ridgway, T. H.; Zimmer, H. J. Polym. Sci., Polym. Chem. 1989, 27, 989-997.
32. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-630.