Summary
Poly[2,5-bis(dimethylsilyl)thiophene] (I), a copolymer with alternating thiophene and disilyl units, has been prepared by the Wurtz coupling of 2,5-bis(dimethylchlorosilyl)thiophene (IV) with sodium metal in toluene. I has been characterized by 1H, 13C, and 29Si NMR, IR, UV, GPC, TGA and elemental analysis. The photolysis of I in benzene/methanol solution results in degradation of the polymer. The structure of the photoproducts and possible mechanisms for their formation are discussed.
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References
West,R. Annals New York Acad. of Sci., 262 (1974).
West, R.; Carberry,E.Science, 189, 179(1975).
West, R. Pure and Applied Chem., 54, 1041 (1982).
Boberski, W. G.; Allred, A.L. J.Organometal.Chem., 88, 65 (1975).
Boberski, W. G.; Allred, A.L. J. Organometal. Chem., 71, C27 (1977).
Yamada,S.; Tokito, S.; Tsutsui, T. Saito, S. Chem. Soc., Chem. Commun., 1449 (1987).
Nate, K.; Ishikawa, M.;Ni, J.;WatanabeH.; Saheki, Y. Organometallics, 6, 1673 (1987).
Miller, R. D.; Hofer, D.; McKean, D. R.; Willson, C. G.; West, R.; Trefonas III, P. T. “Soluble Polysilane Derivatives: Interesting New Radiation-Sensitive Polymers” in “Materials for Microlithography” ed, Thompson, L. F.; Willson, C. G.; Frechet, J. M. J. Amer. Chem. Soc., Washington, D.C. 1984, p. 293–310.
Corfield, G. C.; Astill, D. T.; Clegg, D. W. “Radiation Stability of Silicon Elastomers” in “Materials for Microlithography” ed., Thompson, L. F.; Willson, C. G.; Frechet, J. M. J. Amer. Chem. Soc., Washington, D.C., 1984, p. 473–480.
Pegg, D.T.; Doddrell, D. M.; Bendall, M.R. J. Chem. Phys., 77, 2745 (1982).
Egorochkin, A.N.; Burov, A. I.;Vyazankin, N.S.;Savushkina, V.I.;Anisimova, V.Z.;Chernyshev, E.A. Dokl. Akad. Nauk SSSR, 184, 351 (1969).
Khorshev, S.Y.; Vyazankin, N.S.;Egorochkin, A.N.; Chernyshev, E.A.; Savushkina, V.I.; Kuz'min, O.V.; Anisimova, V.Z. Khim. Geterotsikl. Soedin., 477 (1974), Khim. Geterotsil. Soedin. 8, 1075 (1984).
Ishikawa, M.;Kumada, M; Sakurai, H. J. Organometal. Chem., 23, 63 (1970).
For a recent review see:Boudjouk, P. J.J. Chem. Educ., 63, 427 (1986).
For a recent review see: Abdulla, R. F.Aldrichimica Acta, 21, 31 (1988).
de Souza-Barboza, J. C.; Petrier, C.;Luche, J. L.J. Org. Chem., 53, 1212 (1988).
Einhorn J.;Luche, J. L. J. Org. Chem., 52, 4124 (1987).
Suslik, K. S.; Casadonte, D. J. J. Am. Chem. Soc., 109, 3459 (1987).
Sakurai, H.; Murakami, M.;Kumada, M. J. Am. Chem. Soc., 91, 519 (1969).
Jung, I. N.;Weber, W. P. J. Org. Chem., 41, 946 (1976).
For a review see: Hengge, E. “Properties and Preparation of Si-Si Linkages” Springer Verlag, Berlin, 1974.
Zhang, X. H.; West, R. J. Polym. Sci. Polym. Chem. Ed., 22, 159 and 225 (1984).
For a recent review see: Ishikawa, M.; Kumada, M. “Advances in Organometal. Chem.” Vol. 19, Ed. Stone F. G. A.; West, R. Academic Press, New York, 1981, p 51–95.
|Hu, S. S.; Weber, W. P. J. Organometal. Chem., in press (1989).
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Hu, SS., Weber, W.P. Synthesis and photodegradation of poly[2,5-bis(dimethylsilyl)thiophene]. Polymer Bulletin 21, 133–140 (1989). https://doi.org/10.1007/BF00266163
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DOI: https://doi.org/10.1007/BF00266163