Skip to main content

Synthesis and Metathesis Polymerization of Cycloadduct Based on Quadricyclane and Perfluoro-1-octene


Previously undescribed norbornene monomer 3,3,4-trifluoro-4-perfluorohexyltricyclononene-7 is synthesized by the [2+2+2] cycloaddition reaction. The monomer is involved in the ring-opening polymerization metathesis in the presence of the first-generation Grubbs catalyst to give rise to the amorphous, glassy unsaturated polymer. The gas-transport properties of the metathesis polymer is studied, the gas permeability and diffusion coefficients for a wide range of gases (He, H2, O2, N2, CO2, CH4) are determined, and the solubility coefficients of gases in this polymer are calculated.

This is a preview of subscription content, access via your institution.

Fig. 1.


  1. T. C. Merkel, V. Bondar, K. Nagai, B. D. Freeman, and Y. P. Yampolskii, Macromolecules 32, 8427 (1999).

    Article  CAS  Google Scholar 

  2. Y. P. Yampolskii, Russ. J. Gen. Chem. 79, 657 (2009).

    Article  CAS  Google Scholar 

  3. I. Pinnau and L. G. Toy, J. Membr. Sci. 109, 125 (1996).

    Article  CAS  Google Scholar 

  4. N. A. Belov, A. A. Zharov, A. V. Shashkin, M. Q. Shaikh, K. Raetzke, and Y. P. Yampolskii, J. Membr. Sci. 383, 70 (2011).

    Article  CAS  Google Scholar 

  5. N. Belov, Y. Nizhegorodova, A. Zharov, I. Konovalova, V. Shantarovich, and Y. Yampolskii, J. Membr. Sci. 495, 431 (2015).

    Article  CAS  Google Scholar 

  6. M. V. Bermeshev, L. E. Starannikova, S. R. Sterlin, A. A. Tyutyunov, A. N. Tavtorkin, Y. P. Yampolskii, and E. S. Finkelshtein, Pet. Chem. 55, 753 (2015).

    Article  CAS  Google Scholar 

  7. I. L. Borisov, T. R. Akmalov, A. O. Ivanov, V. V. Volkov, E. S. Finkelshtein, and M. V. Bermeshev, Mendeleev Commun. 26, 124 (2016).

    Article  CAS  Google Scholar 

  8. C. D. Smith, Org. Synth. 51, 133 (1971).

    Article  CAS  Google Scholar 

  9. M. Macchione, J. C. Jansen, G. De Luca, E. Tocci, M. Longeri, and E. Drioli, Polymer 48, 2619 (2007).

    Article  CAS  Google Scholar 

  10. M. L. Gringolts, M. V. Bermeshev, Y. V. Rogan, M. V. Moskvicheva, M. P. Filatova, E. S. Finkelshtein, and G. N. Bondarenko, Silicon 7, 107 (2015).

    Article  CAS  Google Scholar 

  11. B. A. Bulgakov, M. V. Bermeshev, D. V. Demchuk, V. G. Lakhtin, A. G. Kazmin, and E. S. Finkelshtein, Tetrahedron 68, 2166 (2012).

    Article  CAS  Google Scholar 

  12. M. V. Bermeshev, A. V. Syromolotov, M. L. Gringolts, V. G. Lakhtin, and E. S. Finkelshtein, Tetrahedron Lett. 52, 6091 (2011).

    Article  CAS  Google Scholar 

  13. G. O. Karpov, M. V. Bermeshev, I. L. Borisov, S. R. Sterlin, A. A. Tyutyunov, N. P. Yevlampieva, B. A. Bulgakov, V. V. Volkov, and E. Sh. Finkelshtein, Polymer 153, 626 (2018).

    Article  CAS  Google Scholar 

  14. J. Vargas, A. A. Santiago, M. A. Tlenkopatchev, M. López-González, and E. Riande, J. Membr. Sci. 361, 78 (2010).

    Article  CAS  Google Scholar 

  15. J. Vargas, A. Martínez, A. A. Santiago, M. A. Tlenkopatchev, R. Gaviño, and M. Aguilar-Vega, J. Fluorine Chem. 130, 162 (2009).

    Article  CAS  Google Scholar 

  16. J. Vargas, A. Martínez, A. A. Santiago, M. A. Tlenkopatchev, and M. Aguilar-Vega, Polymer 48, 6546 (2007).

    Article  CAS  Google Scholar 

  17. T. Masuda, Y. Iguchi, B.-Z. Tang, and T. Higashimura, Polymer 29, 2041 (1988).

    Article  CAS  Google Scholar 

  18. G. Li, Y. Shen, and Q. Ren, J. Appl. Polym. Sci. 97, 2192 (2005).

    Article  CAS  Google Scholar 

  19. H. Tan, X. Xie, J. Li, Y. Zhong, and Q. Fu, Polymer 45, 1495 (2004).

    Article  CAS  Google Scholar 

  20. S. Kong, A. O. Borissova, S. B. Lesnichin, M. Hartl, L. L. Daemen, J. Eckert, M. Y. Antipin, and I. G. Shenderovich, J. Phys. Chem. A 115, 8041 (2011).

    Article  CAS  PubMed  Google Scholar 

Download references


This work was supported by the Russian Science Foundation, project 17-73-10499.

Author information

Authors and Affiliations


Corresponding author

Correspondence to M. V. Bermeshev.

Additional information

Translated by T. Soboleva

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karpov, G.O., Bakhtin, D.S., Bermeshev, M.V. et al. Synthesis and Metathesis Polymerization of Cycloadduct Based on Quadricyclane and Perfluoro-1-octene. Polym. Sci. Ser. B 61, 387–394 (2019).

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: