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Metathesis polymer based on 5-trimethylsilylbicyclo[2.2.2]oct-2-ene: Synthesis and gas-transport properties

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Abstract

A new silicon-containing bicyclic monomer 5-trimethylsilylbicyclo[2.2.2]oct-2-ene has been synthesized, and its metathesis polymerization and gas transport properties of the polymer based on it have been studied. The monomer is synthesized by the two-step scheme using the Diels–Alder reaction from 1,3-cyclohexadiene and vinyltrichlorosilane followed by methylation with a Grignard reagent. The resulting 5-trimethylsilylbicyclo[ 2.2.2]oct-2-ene is inactive in metathesis homopolymerization in the presence of first- and second- generation Grubbs catalysts and a Hoveyda–Grubbs catalyst, but it slowly polymerizes when norbornene is present in the reaction mixture. The high-molecular-mass copolymer (M w = 3.0 × 105, M w/M n = 2.8) of 5-trimethylsilylbicyclo[2.2.2]oct-2-ene and norbornene possesses good film-forming properties, and its glass transition temperature is 126°C. The gas-transport properties of the copolymer have been studied.

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References

  1. E. S. Finkelshtein, K. L. Makovetskii, Y. P. Yampol’skii, E. B. Portnykh, I. Y. Ostrovskaya, N. E. Kaliuzhnyi, N. A. Pritula, A. I. Gol’berg, M. S. Yatsenko, and N. A. Platé, Makromol. Chem. 192 (1), 1 (1991).

    Article  CAS  Google Scholar 

  2. E. S. Finkelshtein, K. L. Makovetskii, M. L. Gringolts, Y. V. Rogan, T. G. Golenko, L. E. Starannikova, Y. P. Yampolskii, V. P. Shantarovich, and T. Suzuki, Macromolecules 39 (20), 7022 (2006).

    Article  CAS  Google Scholar 

  3. M. Gringolts, M. Bermeshev, Y. Yampolskii, L. Starannikova, V. Shantarovich, and E. Finkelshtein, Macromolecules 43 (17), 7165 (2010).

    Article  CAS  Google Scholar 

  4. M. V. Bermeshev, A. V. Syromolotov, L. E. Starannikova, M. L. Gringolts, V. G. Lakhtin, Y. P. Yampolskii, and E. S. Finkelshtein, Macromolecules 46 (22), 8973 (2013).

    Article  CAS  Google Scholar 

  5. P. P. Chapala, M. V. Bermeshev, L. E. Starannikova, N. A. Belov, V. E. Ryzhikh, V. P. Shantarovich, V. G. Lakhtin, N. N. Gavrilova, Y. P. Yampolskii, and E. S. Finkelshtein, Macromolecules 48 (22), 8055 (2015).

    Article  CAS  Google Scholar 

  6. M. Bermeshev, B. Bulgakov, D. Demchuk, M. Filatova, L. Starannikova, and E. Finkelshtein, Polym. J. 45 (7), 718 (2013).

    Article  CAS  Google Scholar 

  7. E. S. Finkelshtein, M. V. Bermeshev, M. L. Gringolts, L. E. Starannikova, and Y. P. Yampolskii, Russ. Chem. Rev. 80 (4), 341 (2011).

    Article  CAS  Google Scholar 

  8. H. B. Park, C. H. Jung, Y. M. Lee, A. J. Hill, S. J. Pas, S. T. Mudie, E. V. Wagner, B. D. Freeman, and D. J. Cookson, Science 318, 254 (2007).

    Article  CAS  Google Scholar 

  9. S. H. Han, N. Misdan, S. Kim, C. M. Doherty, A. J. Hill, and Y. M. Lee, Macromolecules 43 (18), 7657 (2010).

    Article  CAS  Google Scholar 

  10. S. Kim and Y. M. Lee, Prog. Polym. Sci. 43, 1 (2015).

    Article  CAS  Google Scholar 

  11. P. M. Budd, B. S. Ghanem, S. Makhseed, N. B. McKeown, K. J. Msayib, and C. E. Tattershall, Chem. Commun. 2004, 230 (2004).

    Article  Google Scholar 

  12. B. S. Ghanem, N. B. McKeown, P. M. Budd, and D. Fritsch, Macromolecules 41, 1640 (2008).

    Article  CAS  Google Scholar 

  13. Y. Rogan, L. Starannikova, V. Ryzhikh, Y. Yampolskii, P. Bernardo, F. Bazzarelli, J. C. Jansen, and N. B. McKeown, Polym. Chem. 4 (13), 3813 (2013).

    Article  CAS  Google Scholar 

  14. M. Carta, R. Malpass-Evans, M. Croad, Y. Rogan, J. C. Jansen, P. Bernardo, F. Bazzarelli, and N. B. McKeown, Science 339 (6117), 303 (2013).

    Article  CAS  Google Scholar 

  15. Olefin Metathesis and Metathesis Polymerization, Ed. by K. J. Ivin and J. C. Mol, (Academic Press, San Diego, CA, 1997), p. 288

  16. P. A. Patton and T. J. McCarthy, Macromolecules 20 (4), 778 (1987).

    Article  CAS  Google Scholar 

  17. J. G. Hamilton, K. J. Ivin, and J. J. Rooney, Br. Polym. J. 17 (1), 41 (1985).

    Article  CAS  Google Scholar 

  18. V. P. Conticello, D. L. Gin, and R. H. Grubbs, J. Am. Chem. Soc. 114 (24), 9708 (1992).

    Article  CAS  Google Scholar 

  19. L. Pu, M. W. Wagaman, and R. H. Grubbs, Macromolecules 29 (4), 1138 (1996).

    Article  CAS  Google Scholar 

  20. E. A. Ofstead and N. Calderon, Makromol. Chem. 154 (1), 21 (1972).

    Article  CAS  Google Scholar 

  21. P. P. Chapala, M. V. Bermeshev, L. E. Starannikova, V. P. Shantarovich, N. N. Gavrilova, V. G. Avakyan, M. P. Filatova, Y. P. Yampolskii, and E. S. Finkelshtein, J. Membr. Sci. 474, 83 (2015).

    Article  CAS  Google Scholar 

  22. M. L. Gringolts, M. V. Bermeshev, L. E. Starannikova, Y. V. Rogan, Y. P. Yampol’skii, and E. S. Finkel’shtein, Polym. Sci., Ser. A 51 (11–12), 1233 (2009).

    Article  Google Scholar 

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Correspondence to M. V. Bermeshev.

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Original Russian Text © D.A. Alent’ev, M.V. Bermeshev, L.E. Starannikova, A.V. Solopchenko, Yu.P. Yampol’skii, E.Sh. Finkelshtein, 2016, published in Vysokomolekulyarnye Soedineniya, Seriya B, 2016, Vol. 58, No. 6, pp. 450–456.

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Alent’ev, D.A., Bermeshev, M.V., Starannikova, L.E. et al. Metathesis polymer based on 5-trimethylsilylbicyclo[2.2.2]oct-2-ene: Synthesis and gas-transport properties. Polym. Sci. Ser. B 58, 659–664 (2016). https://doi.org/10.1134/S1560090416060014

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