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Polyacetylenes with substituents: Their synthesis and properties

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Catalytical and Radical Polymerization

Part of the book series: Advances in Polymer Science ((volume 81))

Abstract

This review deals with recent advances in the synthesis, characterization, and function of polyacetylenes with substituents (substituted polyacetylenes). The main features are as follows: A number of catalysts based on group 5 and 6 transition metals (Nb, Ta, Mo, W) have been exploited which polymerize substituted acetylenes, especially sterically crowded ones. By using these catalysts, new substituted polyacetylenes

with molecular weight up to one million have been synthesized from various monomers; e.g., HC≡C-t-Bu, MeC≡C-n-C5H11, MeC≡CPh, ClC≡CPh, and MeC≡CSiMe3. Unlike polyacetylene, these substituted polyacetylenes are generally colorless (or light yellow), soluble, amorphous, air-stable, electrically insulating, and non-paramagnetic. Some of these polymers have been found to be useful as membranes for separation of gases and liquids, thus constituting a new category of speciality polymers.

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8 References

  1. Chien, J. C. W.: Polyacetylene. Academic Press, New York 1984

    Google Scholar 

  2. Gibson, H. W., Porchan, J. M., in: Encyclopedia of Polymer Science and Engineering. 2nd ed., Vol. 1, Kvoschwitz, J. I. (Editor-in-Chief), Wiley & Sons, New York 1984, p. 87

    Google Scholar 

  3. Review by: Wegner, G.: Angew. Chem. Int. Ed. Engl. 20, 361 (1981)

    Article  Google Scholar 

  4. Review by: Simionescu, C. I., Percec, V.: Prog. Polym. Sci. 8, 133 (1982)

    Article  CAS  Google Scholar 

  5. Review by: Chauser, M. G., Rodionov, Yu. M., Misin, V. M., Cherkashin, M. I.: Russ. Chem. Rev. (Engl. Trans.) 45, 348 (1976); Usp. Khim. 45, 695 (1976)

    Article  Google Scholar 

  6. Masuda, T., Hasegawa, K., Higashimura, T.: Macromolecules 7, 728 (1974)

    Article  CAS  Google Scholar 

  7. Masuda, T., Higashimura, T.: Acc. Chem. Res. 17, 51 (1984)

    Article  CAS  Google Scholar 

  8. Woon, P. S., Farona, M. F.: J. Polym. Sci., Polym. Chem. Ed. 12, 1749 (1974)

    Article  CAS  Google Scholar 

  9. Katz, T. J., Lee, S. J.: J. Am. Chem. Soc. 102, 422 (1980)

    Article  CAS  Google Scholar 

  10. Katz, T. J., Ho, T.-H., Shih, N.-Y., Ying, Y.-C., Stuart, V. I. W.: J. Am. Chem. Soc. 106, 2658 (1984)

    Google Scholar 

  11. Meziane, D., Soum, A., Fontanille, M., Rudler, H.: Makromol. Chem. 186, 367 (1985)

    Article  CAS  Google Scholar 

  12. Voronkov, M. G., Pukhnarevich, V. B., Sushchinskaya, S. P., Annenkova, V. Z., Annenkova, V. M., Andreeva, N. J.: J. Polym. Sci., Polym. Chem. Ed. 18, 53 (1980)

    Article  CAS  Google Scholar 

  13. Aldissi, M., Linaya, C., Sledz, J., Schue, F., Giral, L., Fabre, J. M., Rolland, M.: Polymer 23, 243 (1982)

    Article  CAS  Google Scholar 

  14. Masuda, T., Okano, Y., Tamura, K., Higashimura, T.: Polymer 26, 793 (1985)

    Article  CAS  Google Scholar 

  15. Levisalles, J., Rose-Munch, F., Rudler, H., Daran, J.-C., Dromzee, Y., Jeannin, Y., Ades, D., Fontanille, M.: J. Chem. Soc., Chem. Commun. 1055 (1981)

    Google Scholar 

  16. Masuda, T., Deng, Y.-X., Higashimura, T.: Bull. Chem. Soc. Jpn. 56, 2798 (1983)

    Article  CAS  Google Scholar 

  17. Masuda, T., Kawasaki, M., Okano, Y., Higashimura, T.: Polym. J. 14, 371 (1982)

    Article  CAS  Google Scholar 

  18. Masuda, T., Okano, Y., Kuwane, T., Higashimura, T.: Polym. J. 12, 907 (1980)

    Article  CAS  Google Scholar 

  19. Okano, Y., Masuda, T., Higashimura, T.: Polym. J. 14, 477 (1982)

    Article  CAS  Google Scholar 

  20. Okano, Y., Masuda, T., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed. 23, 2527 (1985)

    Article  CAS  Google Scholar 

  21. Masuda, T., Thieu, K.-Q., Sasaki, N., Higashimura, T.: Macromolecules 9, 661 (1976)

    Article  CAS  Google Scholar 

  22. Masuda, T., Takahashi, T., Yamamoto, K., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed. 20, 2603 (1982)

    Article  CAS  Google Scholar 

  23. Masuda, T., Yamamoto, K., Higashimura, T.: Polymer 23, 1663 (1982)

    Article  CAS  Google Scholar 

  24. Hasegawa, K.: Europ. Polym. J. 13, 315 (1977)

    Article  CAS  Google Scholar 

  25. Ohtori, T., Masuda, T., Higashimura, T.: Polym. J. 11, 805 (1979)

    Article  CAS  Google Scholar 

  26. Liaw, D. J., Soum, A., Fontanille, M., Parlier, A., Rudler, H.: Makromol. Chem. Rapid Commun. 6, 309 (1985)

    Article  CAS  Google Scholar 

  27. Higashimura, T., Deng, Y.-X., Masuda, T.: Macromolecules 15, 234 (1982)

    Article  CAS  Google Scholar 

  28. Masuda, T., Kuwane, Y., Higashimura, T.: Polym. J. 13, 301 (1981)

    Article  CAS  Google Scholar 

  29. Masuda, T., Takahashi, T., Niki, A., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed. 24, 809 (1986)

    Article  CAS  Google Scholar 

  30. Sasaki, N., Masuda, T., Higashimura, T.: Macromolecules 9, 664 (1976)

    Article  CAS  Google Scholar 

  31. Hasegawa, K.: Europ. Polym. J. 13, 47 (1977)

    Article  CAS  Google Scholar 

  32. Masuda, T., Takahashi, T., Higashimura, T.: Macromolecules 18, 311 (1985)

    Article  CAS  Google Scholar 

  33. Masuda, T., Kawai, H., Ohtori, T., Higashimura, T.: Polym. J. 11, 813 (1979)

    Article  CAS  Google Scholar 

  34. Okano, Y., Masuda, T., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed. 22, 1603 (1984)

    Article  CAS  Google Scholar 

  35. Tajima, H., Masuda, T., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed., submitted

    Google Scholar 

  36. Masuda, T., Tajima, H., Higashimura, T.: to be published

    Google Scholar 

  37. Calini, C., Chien, J. C. W.: J. Polym. Sci., Polym. Chem. Ed. 22, 2749 (1984)

    Article  Google Scholar 

  38. Ho, T. H., Katz, T. J.: J. Mol. Cat. 28, 359 (1985)

    Article  CAS  Google Scholar 

  39. Kiyashkina, Zh. S., Pomogailo, A. D., Kuzayev, A. I., Lagodzinskaya, G. V., Dyachkovskii, F. S.: J. Polym. Sci., Polym. Symp. No 68, 13 (1980)

    Google Scholar 

  40. Masuda, T., Kawai, M., Higashimura, T.: Polymer 23, 744 (1982)

    Article  CAS  Google Scholar 

  41. Muramatsu, H., Ueda, T., Ito, K.: Macromolecules 18, 1634 (1985)

    Article  CAS  Google Scholar 

  42. Masuda, T., Kuwane, Y., Yamamoto, K., Higashimura, T.: Polym. Bull. 2, 823 (1980)

    Article  CAS  Google Scholar 

  43. Pomogailo, A. D., Kiyashikina, Zh. S., Kuzaev, A. I., Yechmaev, S. B., Ivleva, I. N., Dyachkovskii, F. S.: Vysokomol. Soedin. 17, 707 (1985)

    Google Scholar 

  44. Kawasaki, M., Masuda, T., Higashimura, T.: Polym. J. 15, 767 (1983)

    Article  CAS  Google Scholar 

  45. Masuda, T., Tamura, K., Higashimura, T.: J. Chem. Soc., Chem. Commun. 1615 (1985)

    Google Scholar 

  46. Masuda, T., Kuwane, Y., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed. 20, 1043 (1982)

    Article  CAS  Google Scholar 

  47. Masuda, T., Yamagata, M., Higashimura, T.: Macromolecules 17, 126 (1984)

    Article  CAS  Google Scholar 

  48. Yamagata, M., Masuda, T., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed. 22, 2275 (1984)

    Article  CAS  Google Scholar 

  49. Tamura, K., Masuda, T., Higashimura, T.: Polym. J. 17, 815 (1985)

    Article  CAS  Google Scholar 

  50. Huang, Y.-Z., Li, J.-S., Zhou, Q.-L., Zhou, J.-Q.: J. Polym. Sci., Polym. Chem. Ed. 23, 1853 (1985)

    Article  CAS  Google Scholar 

  51. Trepka, W. J., Sonnenfeld, R. J.: J. Polym. Sci., Part A-1 8, 2721 (1970)

    CAS  Google Scholar 

  52. Dändliker, G.: Helv. Chim. Acta, 52, 1482 (1969)

    Article  Google Scholar 

  53. Masuda, T., Mouri, T., Higashimura, T.: Bull. Chem. Soc. Jpn. 53, 1152 (1980)

    Article  CAS  Google Scholar 

  54. Masuda, T., Takahashi, T., Higashimura, T.: J. Chem. Soc., Chem. Commun. 1297 (1982)

    Google Scholar 

  55. Cotton, F. A., Hall, W. T., Cann, K. J., Karol, F. J.: Macromolecules 14, 233 (1981)

    Article  CAS  Google Scholar 

  56. Takahashi, T., Masuda, T., Higashimura, T.: Polymer Preprints, Jpn. 31 (6), 1193 (1982)

    Google Scholar 

  57. Masuda, T., Niki, A., Isobe, E., Higashimura, T.: Macromolecules, 18, 2109 (1985)

    Article  CAS  Google Scholar 

  58. Niki, A., Masuda, T., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed., submitted

    Google Scholar 

  59. Masuda, T., Isobe, E., Higashimura, T., Takada, K.: J. Am. Chem. Soc. 105, 7473 (1983)

    Article  CAS  Google Scholar 

  60. Masuda, T., Isobe, E., Higashimura, T.: Macromolecules 18, 841 (1985)

    Article  CAS  Google Scholar 

  61. Masuda, T., Isobe, E., Hamano, T., Higashimura, T.: Macromolecules, in press

    Google Scholar 

  62. Masuda, T., Isobe, E., Hamano, T., Higashimura, T.: J. Polym. Sci., Polym. Chem. Ed., in press

    Google Scholar 

  63. Isobe, E., Masuda, T., Higashimura, T., Yamamoto, A.: J. Polym. Sci., Polym. Chem. Ed., in press

    Google Scholar 

  64. Nagase, Y.: private communication

    Google Scholar 

  65. Yoshimura, T., Masuda, T., Higashimura, T., Ishihara, T.: J. Polym. Sci., Polym. Chem. Ed., in press

    Google Scholar 

  66. Masuda, T., Sasaki, N., Higashimura, T.: Macromolecules 8, 717 (1975)

    Article  CAS  Google Scholar 

  67. Ivin, K. J.: Olefin Metathesis. Academic Press, New York 1983

    Google Scholar 

  68. Grubbs, R. H., in: Comprehensive Organometallic Chemistry. Wilkinson, G., Stone, R. G. A., Abel, E. W. (Eds.), Pergamon Press, New York 1982, Vol. 8, p. 499

    Chapter  Google Scholar 

  69. Review by: Dolgoplosk, B. A., Korshak, Yu. V.: Russ. Chem. Rev. (Engl. Trans.) 53, 36 (1984); Usp. Khim. 53, 65 (1984)

    Article  Google Scholar 

  70. Review by: Dötz, K. H.: Angew. Chem. Int. Ed. Engl. 23, 587 (1984)

    Article  Google Scholar 

  71. Hein, P. R.: J. Polym. Sci., Polym. Chem. Ed. 11, 163 (1973)

    Article  CAS  Google Scholar 

  72. Alimuniar, A. B., Edwards, J. H., Feast, W. J.: J. Mol. Cat. 28, 313 (1985)

    Article  CAS  Google Scholar 

  73. Krausz, P., Garnier, F., Dubois, J.-E.: J. Am. Chem. Soc. 97, 437 (1975)

    Article  CAS  Google Scholar 

  74. Agapiou, A., McNelis, E.: J. Chem. Soc., Chem. Commun. 187 (1975)

    Google Scholar 

  75. Katz, T. J., Acton, N.: Tetrahedron Lett. 4251 (1976)

    Google Scholar 

  76. McGinnis, J., Katz, T. J., Hurwitz, S.: J. Am. Chem. Soc. 98, 605 (1976)

    Article  CAS  Google Scholar 

  77. Katz, T. J., Hacker, S. M., Kendrick, R. D., Yannoni, C. S.: J. Am. Chem. Soc., 107, 2182 (1985)

    Article  CAS  Google Scholar 

  78. Clarke, T. C., Yannoni, C. S., Katz, T. J.: J. Am. Chem. Soc. 105, 7787 (1983)

    Article  CAS  Google Scholar 

  79. Garnier, F., Krausz, P., Rudler, H.: J. Organomet. Chem. 186, 77 (1980)

    Article  CAS  Google Scholar 

  80. Landon, S. J., Shulman, P. M., Geoffroy, G. L.: J. Am. Chem. Soc. 107, 6739 (1985)

    Article  CAS  Google Scholar 

  81. Filippo, Jr., J. S., Sowinski, A. F., Romano, L. J.: J. Am. Chem. Soc. 97, 1599 (1975)

    Article  Google Scholar 

  82. Masuda, T.: Yuki Gosei Kagaku 43, 744 (1985)

    Article  CAS  Google Scholar 

  83. McAlister, D. R., Bercaw, J. E., Bergman, R. G.: J. Am. Chem. Soc. 99, 1666 (1977)

    Article  CAS  Google Scholar 

  84. Yamazaki, H., Wakatsuki, Y.: J. Organomet. Chem. 139, 157, 169 (1977)

    Article  CAS  Google Scholar 

  85. Hasegawa, K., Masuda, T., Higashimura, T.: Macromolecules 8, 255 (1975)

    Article  CAS  Google Scholar 

  86. Masuda, T., Higashimura, T.: Macromolecules 12, 9 (1979)

    Article  CAS  Google Scholar 

  87. Masuda, T., Yoshizawa, T., Okano, Y., Higashimura, T.: Polymer 25, 503 (1984)

    Article  CAS  Google Scholar 

  88. Percec, V.: Polym. Bull. 10, 1 (1983), and references therein

    Google Scholar 

  89. Ito, T., Shirakawa, H., Ikeda, S.: J. Polym. Sci., Polym. Chem. Ed. 12, 11 (1974)

    Article  CAS  Google Scholar 

  90. Simionescu, C. I., Percec, V.: J. Polym. Symp. No. 67, 43 (1980)

    Google Scholar 

  91. Yamanobe, T., Ando, I., Chujo, R.: Polym. J. 14, 827 (1982)

    Article  CAS  Google Scholar 

  92. Leclerc, M., Prud'homme, R. E.: J. Polym. Sci., Polym. Phys. Ed. 23, 2021 (1985)

    Article  CAS  Google Scholar 

  93. Leclerc, M., Prud'homme, R. E., Soum, A., Fontanille, M.: J. Polym. Sci., Polym. Phys. Ed. 23, 2031 (1985)

    Article  CAS  Google Scholar 

  94. Sondheimer, F., Ben-Efraim, D. A., Wolovsky, R.: J. Am. Chem. Soc. 83, 1675 (1961)

    Article  CAS  Google Scholar 

  95. Ito, T., Shirakawa, H., Ikeda, S.: J. Polym. Sci., Polym. Chem. Ed. 13, 1943 (1975)

    Article  CAS  Google Scholar 

  96. Masuda, T., Tang, B.-Z., Higashimura, T., Yamaoka, H.: Macromolecules 18, 2369 (1985)

    Article  CAS  Google Scholar 

  97. Will, F. G., McKee, D. W.: J. Polym. Sci., Polym. Chem. Ed. 21, 2379 (1983)

    Article  Google Scholar 

  98. Masuda, T., Tang, B.-Z., Tanaka, A., Higashimura, T.: Macromolecules, 19, 1459 (1986)

    Article  CAS  Google Scholar 

  99. Shirakawa, H., Louis, E. J., MacDiarmid, A. G., Chiang, C. K., Heeger, A. J.: J. Chem. Soc., Chem. Commun. 578 (1977)

    Google Scholar 

  100. Kang, E. T., Bhatt, A. P., Villaroel, E., Anderson, W. A., Ehrlich, P.: J. Polym. Sci., Polym. Lett. Ed. 20, 143 (1982)

    Article  CAS  Google Scholar 

  101. Cukor, P., Krugler, J. I., Rubner, M. F.: Makromol. Chem. 182, 165 (1981)

    Article  CAS  Google Scholar 

  102. Ito, T.: PhD thesis, Tokyo Institute of Technology, 1974

    Google Scholar 

  103. Kang, E. T., Ehrlich, P., Bhatt, A. P., Anderson, W. A.: Macromolecules, 17, 1020 (1984)

    Article  CAS  Google Scholar 

  104. Review by: Lonsdale, H. K.: J. Membrane Sci. 10, 81 (1982)

    Article  CAS  Google Scholar 

  105. Takada, K., Matsuya, H., Masuda, T., Higashimura, T.: J. Appl. Polym. Sci. 30, 1605 (1985)

    Article  CAS  Google Scholar 

  106. Higashimura, T., Masuda, T., Okada, M.: Polym. Bull. 10, 114 (1983)

    Article  CAS  Google Scholar 

  107. Masuda, T., Iguchi, Y., Tang, B.-Z., Higashimura, T.: to be published

    Google Scholar 

  108. Yasuda, H., Stannett, V., in: Polymer Handbook. 2nd ed. Brandrup, J., Immergut, E. H. (Eds.), Wiley-Interscience, New York 1975, p. III–229

    Google Scholar 

  109. Nakagawa, T., Saito, T., Saito, Y., Asakawa, S.: Polymer Preprints, Jpn. 34 (7), 1885 (1985)

    Google Scholar 

  110. Odani, H., Shimomura, H., Nakanishi, K., Kurata, M., Masuda, T., Higashimura, T.: Kobunshi Ronbunshu, submitted

    Google Scholar 

  111. Kimura, S., Nomura, T.: Membrane 7, 353 (1982)

    CAS  Google Scholar 

  112. Mulder, M. H. V., Hendrikman, J. O., Hegeman, H., Smolders, C. A.: J. Membrane Sci. 16, 269 (1983)

    Article  CAS  Google Scholar 

  113. Masuda, T., Tang, B.-Z., Higashimura, T.: Polym. J., 18, 565 (1986). Cf. Japanese Patent S60-75306 (1985)

    Article  CAS  Google Scholar 

  114. Fusaoka, Y., Imadzu, M., Kawabe, M.: Abstracts I of 51st Autumnal meeting of Chem. Soc. Jpn., Kanazawa, 1985, p. 501

    Google Scholar 

  115. Ishihara, K., Nagase, Y., Matsui, K.: Makromol. Chem., Rapid Commun. 7, 43 (1986)

    Article  CAS  Google Scholar 

  116. Review by: Steppan, H., Buhr, G., Vollmann, H.: Angew. Chem. Int. Ed. Engl. 21, 455 (1982)

    Article  Google Scholar 

  117. Higashimura, T., Tang, B.-Z., Masuda, T., Yamaoka, H., Matsuyama, T.: Polym. J. 17, 393 (1985)

    Article  CAS  Google Scholar 

  118. Chapiro, A. in: Ref. 108, p. II–481

    Google Scholar 

  119. Brandzma, L., Verkrujisse, H. D.: Synthesis of Acetylenes, Allens and Cumulenes. Elsevier, Amsterdam 1981

    Google Scholar 

  120. Ben-Efraim, D. A., in: The Chemistry of the Carbon—Carbon Triple Bond. Part 2, Pati, S. (Ed.), J. Wiley, Chichester 1978, Chap. 18

    Google Scholar 

  121. Masuda, T. in: Kobunshi Deita Handobukku (in Japanese). Furukawa, J. (Ed.), Baifuukan, Tokyo 1985, p. I–1–4

    Google Scholar 

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  1. Department of Polymer Chemistry, Faculty of Engineering, Kyoto University, 606, Kyoto, Japan

    Toshio Masuda & Toshinobu Higashimura

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  1. Toshio Masuda
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Masuda, T., Higashimura, T. (1987). Polyacetylenes with substituents: Their synthesis and properties. In: Catalytical and Radical Polymerization. Advances in Polymer Science, vol 81. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0037614

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