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Cyclopolymerization of 1,1-Dipropargyl-1-silacyclohexane by Transition Metal Catalysts

  • Gal, Yeong-Soon (Polymer Chemistry Laboratory, College of General Education, Kyungil University) ;
  • Lee, In-Sook (Department of Chemistry, Kyungpook National University) ;
  • Chang, Eun-Hee (Department of Chemistry, Kyungpook National University) ;
  • Jeong, Yun-Cheol (R&D Center, Heesung Electronics LTD.) ;
  • Kwak, Young-Woo (Department of Chemistry, Kyungpook National University)
  • Published : 2007.08.20

Abstract

A conjugated spirocyclic polymer was synthesized via the cyclopolymerization of 1,1-dipropargyl-1- silacyclohexane with various transition metal catalysts. The monomer, 1,1-dipropargyl-1-silacyclohexane was synthesized by Grignard reaction of 1,1-dichloro-1-silacyclohexane with propargyl magnesium bromide. This polymerization proceeded well to give the corresponding poly(1,1-dipropargyl-1-silacyclohexane). The catalytic activity of WCl6 was found to be similar with that of MoCl5. The structure of polymer having the conjugated backbone with silacyclohexane moieties was characterized by such instrumental methods as NMR (1H-, 13C-), IR, and UV-visible spectroscopies. The resulting polymers were mostly yellow or light-brown powders, depending on the catalyst systems used. This polymer was completely soluble in halogenated and aromatic hydrocarbons such as chloroform, 1,2-dichloromethane, benzene, toluene, and chlorobenzene, etc. The thermal and oxidative stabilities of polymer were also studied and discussed.

Keywords

References

  1. Greenham, S. C.; Moratti, S. C.; Bradley, D. D. C.; Friend, R. H.; Holmes, A. B. Nature 1993, 365, 628 https://doi.org/10.1038/365628a0
  2. Jin, S. H.; Kim, M. Y.; Kim, J. Y.; Lee, K.; Gal, Y. S. J. Am. Chem. Soc. 2004, 126, 2474 https://doi.org/10.1021/ja036955+
  3. Park, S. M.; Lee, H. J. Bull. Korean Chem. Soc. 2005, 26, 697 https://doi.org/10.5012/bkcs.2005.26.5.697
  4. Kertesz, M.; Choi, C. H.; Yang, S. Chem. Rev. 2005, 105, 3448 https://doi.org/10.1021/cr990357p
  5. Sun, A.; Lauher, J. W.; Goroff, N. S. Science 2006, 312, 1030 https://doi.org/10.1126/science.1124621
  6. Ito, T.; Shirakawa, H.; Ikeda, S. J. Polym. Sci.: Part A: Polym. Chem. 1974, 12, 11 https://doi.org/10.1002/pol.1974.170120102
  7. Masuda, T.; Higashimura, T. Adv. Polym. Sci. 1981, 81, 121
  8. Choi, S. K.; Lee, J. H.; Kang, S. J.; Jin, S. H. Prog. Polym. Sci. 1997, 22, 693 https://doi.org/10.1016/S0079-6700(97)00002-6
  9. Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565 https://doi.org/10.1021/cr990248a
  10. Choi, S. K.; Gal, Y. S.; Jin, S. H.; Kim, H. K. Chem. Rev. 2000, 100, 1645 https://doi.org/10.1021/cr960080i
  11. Anders, U.; Nuyken, O.; Buchmeiser, M. R. J. Mol. Cat. A: Chem. 2004, 213, 89 https://doi.org/10.1016/j.molcata.2003.10.052
  12. Gal, Y. S.; Jin, S. H.; Choi, S. K. J. Mol. Cat. A: Chem. 2004, 213, 115 https://doi.org/10.1016/j.molcata.2003.10.055
  13. Gal, Y. S.; Jin, S. H.; Lee, H. S.; Kim, S. Y. Macromol. Res. 2005, 13, 491 https://doi.org/10.1007/BF03218486
  14. Lam, J. W. Y.; Tang, B. Z. Acc. Chem. Res. 2005, 38, 745 https://doi.org/10.1021/ar040012f
  15. Mayershofer, M. G.; Nuyken, O.; Buchmeiser, M. R. Macromolecules 2006, 39, 3484 https://doi.org/10.1021/ma052510p
  16. Gal, Y. S.; Choi, S. K. J. Appl. Polym. Sci. 1993, 50, 601 https://doi.org/10.1002/app.1993.070500404
  17. Sakaguchi, T.; Yumoto, K.; Shida, Y.; Shiotsuki, M.; Sanda, F.; Masuda, T. J. Polym. Sci.: Part A: Polym. Chem. 2006, 44, 5028 https://doi.org/10.1002/pola.21622
  18. Gal, Y. S.; Lim, K. T.; Shim, S. Y.; Kim, S. H.; Koh, K.; Jang, S. H.; Jin, S. H. Syn. Met. 2005, 154, 169 https://doi.org/10.1016/j.synthmet.2005.07.043
  19. Furlani, A.; Iucci, G.; Russo, M. V.; Bearzotti, A.; D'mico, A. Sensors and Actuators B 1992, 7, 447 https://doi.org/10.1016/0925-4005(92)80341-T
  20. Samuel, D. W.; Ledoux, I.; Dhenaut, C.; Zyss, J.; Fox, H. H.; Schrock, R. R.; Silbey, R. J. Science 1994, 265, 1070 https://doi.org/10.1126/science.265.5175.1070
  21. Tada, K.; Hidayat, R.; Hirohata, M.; Teraguchi, M.; Masuda, T.; Yoshino, K. Jpn. J. Appl. Phys. 1996, 35, L1138 https://doi.org/10.1143/JJAP.35.L1138
  22. Gal, Y. S.; Lee, W. C.; Kim, S. Y.; Park, J. W.; Jin, S. H.; Koh, K. N.; Kim, S. H. J. Polym. Sci.: Part A: Polym. Chem. 2001, 39, 3151 https://doi.org/10.1002/pola.1297
  23. Butler, G. B. Acc. Chem. Res. 1982, 15, 370 https://doi.org/10.1021/ar00083a005
  24. Stille, J. K.; Frey, D. A. J. Am. Chem. Soc. 1961, 83, 1697 https://doi.org/10.1021/ja01468a034
  25. Gibson, G. B.; Bailey, F. C.; Epstein, A. J.; Rommelmann, H.; Kaplan, S.; Pochan, J. M. J. Am. Chem. Soc. 1983, 105, 4417 https://doi.org/10.1021/ja00351a048
  26. Gal, Y. S.; Jin, S. H.; Kim, S. H.; Lee, H. J.; Shim, S. Y.; Lim, K. T. J. Ind. Eng. Chem. 2004, 10, 911 https://doi.org/10.1021/ie50107a014
  27. Kim, Y. H.; Gal, Y. S.; Kim, U. Y.; Choi, S. K. Macromolecules 1988, 21, 1991 https://doi.org/10.1021/ma00185a017
  28. Gal, Y. S.; Choi, S. K. J. Polym. Sci.: Part A: Polym. Chem. 1987, 25, 2323 https://doi.org/10.1002/pola.1987.080250827
  29. Gal, Y. S.; Choi, S. K.; Kim, J. Y. J. Polym. Sci.: Part A: Polym. Chem. 1989, 27, 31 https://doi.org/10.1002/pola.1989.080270103
  30. Tsuchihara, K.; Masuda, T.; Higashimura, T. J. Am. Chem. Soc., 1991, 113, 8548 https://doi.org/10.1021/ja00022a066
  31. West, R. J. Am. Chem. Soc. 1954, 76, 6012 https://doi.org/10.1021/ja01652a035
  32. Gal, Y. S.; Jung, B.; Kim, J. H.; Lee, W. C.; Choi, S. K. J. Polym. Sci.: Part A: Polym. Chem. 1991, 33, 307 https://doi.org/10.1002/pola.1995.080330212
  33. Gal, Y. S.; Jung, B.; Lee, W. C.; Lee, H. J.; Choi, S. K. Macromolecules 1995, 28, 2086 https://doi.org/10.1021/ma00110a048
  34. Gal, Y. S.; Jin, S. H.; Gui, T. L.; Lee, W. C.; Yun, N. G.; Park, S. H.; Lee, S. S.; Bae, J. S. J. Ind. Eng. Chem. 2005, 11, 432
  35. Gal, Y. S.; Choi, S. K. Polymer (Korea) 1987, 11, 563
  36. Kim, S. H.; Choi, S. J.; Park, J. W.; Cho, H. N.; Choi, S. K. Macromolecules 1994, 27, 2339 https://doi.org/10.1021/ma00086a059
  37. Gal, Y. S.; Jin, S. H.; Park, J. W.; Lee, W. C.; Lee, H. S.; Kim, S. Y. J. Polym. Sci.: Part A: Polym. Chem. 2001, 39, 4101 https://doi.org/10.1002/pola.10061
  38. Jang, M. S.; Kwon, S. K.; Choi, S. K. Macromolecules 1990, 23, 4135 https://doi.org/10.1021/ma00220a017
  39. Gal, Y. S.; Lee, W. C.; Jin, S. H.; Lee, H. J.; Kim, S. Y.; Kim, D. W.; Ko, J. M.; Chun, J. H. J. Macromol. Sci.-Pure and Appl. Chem. 2001, A38, 263

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