Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Characterization of Oligomers Composed of Alternating 2,5-Bis(ethynylenedimethylsilylene)thienylene and Arylene Units

  • Kwak, Young-Woo (Department of Chemistry, Kyungpook National University) ;
  • Lee, Kyung-Koo (Department of Chemistry, Kyungpook National University) ;
  • Cha, Seung-Hun (Department of Chemistry, Kyungpook National University) ;
  • Lee, Sang-Koo (Department of Chemistry, Kyungpook National University) ;
  • Lee, In-Sook (Department of Chemistry, Kyungpook National University) ;
  • Park, Yong-Tae (Department of Chemistry, Kyungpook National University) ;
  • Lee, Jae-Keun (Department of Chemistry, Kyungpook National University) ;
  • Yoh, Soo-Dong (Department of Chemistry Education, Kyungpook National University) ;
  • Kim, Woo-Sik (Department of Polymer Science, Kyungpook National University)
  • Published : 2003.04.20
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Abstract

The reactions of 2,5-bis(ethynyldimethylsilyl)thiophene (1) with aromatic dihalides(1,4-dibromobenzene, 4,4'- dibromobiphenyl, 9,10-dibromoanthracene, 2,5-dibromopyridine, 2,5-dibromothiophene, and 2,6-diiodo-4- nitroaniline) were carried out in the presence of a $[(PPh_3)_2PdCl_2]$-CuI catalyst in refluxing triethylamine to give poly{[2,5-bis(ethynylenedimethylsilylene)thienylene](arylene)} (2-7) with molecular weights of 2200-7400. The oligomers reveal characteristic absorption in the UV/visible region. The thermal behavior of 2-7 was examined by thermogravimetric analysis in an argon atmosphere.

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References

  1. Corriu, R. J. P.; Devylder, N.; Guérin, C.; Henner, B.; Jean, A.Organometallics 1994, 13, 3194 https://doi.org/10.1021/om00020a036
  2. Ishikawa, M.; Ohshita, J. Silicon and Germanium Containing Conductive Polymers in Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; Wiley: New York, 1997; Vol. 2. Chapter 15
  3. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
  4. Cassar, L. J. Organomet. Chem. 1975, 93, 253. https://doi.org/10.1016/S0022-328X(00)94048-8
  5. Dieck, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. https://doi.org/10.1016/S0022-328X(00)94049-X
  6. Havens, S. J. Polym. Sci. Polym. Lett. Ed. 1985, 23, 587. https://doi.org/10.1002/pol.1985.130231108
  7. Trumbo, D. L.; Marvel, C. S. J. Polym. Sci. A Polym. Chem. 1986, 24, 2311. https://doi.org/10.1002/pola.1986.080240924
  8. Trumbo, D. L.; Marvel, C. S. J. Polym. Sci. A Polym. Chem. 1986, 24, 2231. https://doi.org/10.1002/pola.1986.080240917
  9. Trumbo, D. L.; Marvel, C. S. J. Polym. Sci. A Polym. Chem. 1987, 25, 839. https://doi.org/10.1002/pola.1987.080250309
  10. Ohshita, J.; Kunai, A. Acta Polym. 1998, 49, 379. https://doi.org/10.1002/(SICI)1521-4044(199808)49:8<379::AID-APOL379>3.0.CO;2-Z
  11. Ohshita, J.; Ishii, M.; Ueno, Y.; Yamashita, A.; Ishikawa, M. Macromolecules 1994, 27, 5583. https://doi.org/10.1021/ma00098a011
  12. Ohshita, J.; Yamashita, A.; Hiraoka, T.; Shimpo, A.; Kunai, A.; Ishikawa, M. Macromolecules 1997, 30, 1540. https://doi.org/10.1021/ma960728t
  13. Ohshita, J.; Shinpo, A.; Kunai, A. Macromolecules 1999, 38, 5998.
  14. Chadwick, D. J.; Willbe, C. J. Chem. Soc., Perkin I 1977, 887.
  15. Ohshita, J.; Kanaya, D.; Ishikawa, M. J. Organomet. Chem. 1994, 468, 55. https://doi.org/10.1016/0022-328X(94)80030-8
  16. Hu, S.-S.; Weber, W. P. Polymer. Bulletin 1989, 21, 133.
  17. Zhang, X. H.; West, R. J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 159 and 225.
  18. Corriu, R. J. P.; Douglas, W. E.; Yang, Z.-X. J. Organomet. Chem. 1993, 456, 35. https://doi.org/10.1016/0022-328X(93)83313-K
  19. Corriu, R. J. P.; Douglas, W. E.; Yang, Z.-X.; Garnier, F.; Yassar, A. J. Organomet. Chem. 1991, 417, C50. https://doi.org/10.1016/0022-328X(91)80205-X
  20. Corriu, R. J. P.; Douglas, W. E.; Yang, Z.-X. J. Polym. Sci. C Polym. Lett. 1990, 28, 431. https://doi.org/10.1002/pol.1990.140281306
  21. Corriu, R. J. P.; Douglas, W. E.;Yang, Z. X.; Karakus, Y.; Cross, G. H.; Bloor, D. J. Organomet. Chem. 1993, 455, 69. https://doi.org/10.1016/0022-328X(93)80382-L
  22. Iwahara, T.; West. R. J. Chem. Soc., Chem. Commun. 1988, 1079.
  23. Ishikawa, M.; Hasegawa, Y.; Hatano, T.; Kunai, A.; Yamanaka, T. Organometallics 1989, 8, 2741. https://doi.org/10.1021/om00113a038
  24. Ishikawa, M.; Horio, T.; Hatano, T.; Kunai, A. Organometallics 1993, 12, 2078. https://doi.org/10.1021/om00030a018
  25. Yuan, C.-H.; West, R. Appl. Organomet. Chem. 1994, 8, 423. https://doi.org/10.1002/aoc.590080417
  26. Kunai, A.; Toyoda, E.; Horata, K.; Ishikawa, M. Organometallics1995, 14, 714. https://doi.org/10.1021/om00002a020
  27. Tamao, K.; Yamaguchi, S.; Shiozaki, M.; Nakagawa, Y.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 5867. https://doi.org/10.1021/ja00040a063
  28. Toyoda, E.; Kunai, A.; Ishikawa, M. Organometallics 1995, 14,1089. https://doi.org/10.1021/om00003a005
  29. Chen, W.; Ijadi-Maghsoodi, S.; Barton, T. J. Polym. Prepr. 1997, 38, 189.
  30. Ohshita, J.; Mimura, N.; Arase, H.; Nodona, M.; Kunai, A.; Komaguchi, K.; Shiotani, M.; Ishikawa, M. Macromolecules 1998, 31, 7985. https://doi.org/10.1021/ma980107v
  31. Sohn, H.; Huddleston, R. R.; Powell, D. R.; West, R.; Oka, K.; Yonghua, X. J. Am. Chem. Soc. 1999, 121, 2935. https://doi.org/10.1021/ja983350i
  32. Sanji, T.; Funaya, M.; Sakurai, H. Chem. Lett. 1999, 547.
  33. Ohshita, J.; Hamaguchi, T.; Toyoda, E.; Kunai, A.; Komaguchi, K.; Shiotani, M.; Ishikawa, M.; Naka, A. Organometallics 1999, 18, 1717. https://doi.org/10.1021/om9805943
  34. Yamaguchi, S.; Goto, T.; Tamao, K. Angew. Chem. Int. Ed. 2000, 39, 1695. https://doi.org/10.1002/(SICI)1521-3773(20000502)39:9<1695::AID-ANIE1695>3.0.CO;2-O
  35. Ohshita, J.; Nodono, M.; Takata, A.; Kai, H.; Adachi, A.; Sakamaki, K.; Okita, K.; Kunai, A. Macromol. Chem. Phys. 2000, 201, 851. https://doi.org/10.1002/(SICI)1521-3935(20000501)201:8<851::AID-MACP851>3.0.CO;2-Y
  36. Shizuka, H.; Obuchi, H.; Ishikawa, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1981, 405.
  37. Sakurai, H. J. Organomet. Chem. 1980, 200, 261. https://doi.org/10.1016/S0022-328X(00)88650-7
  38. Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Patai, S.,Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; Vol. 1, p 57.
  39. Kato, J.; Nakamura, K.; Yamasaki, S.; Tokushige, K.; Amano, T. J. Polym. Sci. A Polym. Chem. 1989, 27, 1853. https://doi.org/10.1002/pola.1989.080270606
  40. Ijadi-Maghsoodi, S.; Pang, Y.; Barton, T. J. J. Polym. Sci. A Polym. Chem. 1990, 28, 955. https://doi.org/10.1002/pola.1990.080280501
  41. Corriu, R. J. P.; Gerbier, P.; Guérin, C.; Henner, B. J. L.; Jean, A.; Mutin, P. H. Organometallics 1992, 11, 2507. https://doi.org/10.1021/om00043a038
  42. Itoh, M.; Mitsuzuka, M.; Iwata, K.; Inoue, K. Macromolecules 1994, 27, 7917. https://doi.org/10.1021/ma00104a056
  43. Park, Y. T.; Seo, I. K.; Kim, Y.-R. Bull. Korean Chem. Soc. 1996, 17, 480. https://doi.org/10.1007/BF02706865
  44. Ohshita, J.; Sumida, T.; Kunai, A.; Adachi, A.; Sakamaki, K.; Okita, K. Macromolecules 2000, 33, 8890. https://doi.org/10.1021/ma0005062
  45. Manhart, S. A.; Adachi, A.; Sakamaki, K.; Okita, K.; Ohshita, J.; Ohno, T.; Hamaguchi, T.; Kunai, A.; Kido, J. J. Organomet. Chem. 1999, 592, 52. https://doi.org/10.1016/S0022-328X(99)00481-7

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