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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 ((POLYMER,volume 81))

Abstract

This review deals with recent advances in the synthesis, characterization, and function of poly-acetylenes 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 [—(—CR=CR′—)n—] with molecular weight up to one million have been synthesizedfrom various monomers; e.g., HC≡C—t—Bu, MeC≡C—n—C5H11, MeC≡CPh, ClC≡CPh, and McC≡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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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. Wegner, G.: Angew. Chem. Int. Ed. Engl. 20, 361 (1981)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  5. Chauser, M. G., Rodionov, Yu. M., M.sin, V. M., Cherkashin, M. I.: Russ. Chem. Rev. (Engl. Trans.) 45, 348 (1976)

    Google Scholar 

  6. Chauser, M. G., Rodionov, Yu. M., M.sin, V. M., Cherkashin, M. I.: Usp. Khim 45, 695 (1976)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

  11. 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 

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

    Article  CAS  Google Scholar 

  13. 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)

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. 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 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

  40. 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 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  65. Nagase, Y.: private communication

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

  69. 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

    Google Scholar 

  70. Dolgoplosk, B. A., Korshak, Yu. V.: Russ. Chem. Rev. (Engl. Trans.) 53, 36 (1984)

    Article  Google Scholar 

  71. Dolgoplosk, B. A., Korshak, Yu. V.: Usp. Khim. 53, 65 (1984)

    CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

  77. Katz, T. J., Acton, N.: Tetrahedron Lett. 42, 51 (1976)

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  90. Percec, V.: Polym. Bull. 10, 1 (1983)

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Google Scholar 

  110. 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 

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

    Google Scholar 

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

    Google Scholar 

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

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  115. Masuda, T., Tang, B.-Z., Higashimura, T.: Polym. J., 18, 565 (1986). Cf. Japanese Patent S6075306(1985)

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

  120. Chapiro, A. in: Ref. 108, p. II-481

    Google Scholar 

  121. Brandzma, L., Verkruijsse, H. D.: Synthesis of Acetylenes, Aliens and Cumulenes. Elsevier, Amsterdam 1981

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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Masuda, T., Higashimura, T. (1986). Polyacetylenes with Substituents: Their Synthesis and Properties. In: Catalytical and Radical Polymerization. Advances in Polymer Science, vol 81. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-15187-7_3

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