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Polymerization of Tricyclononenes

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Abstract

The expansion of the range of available and reactive monomers allowing preparation of novel polymeric materials, is an actual task of polymer chemistry. This mini-review is devoted to the polymerization of tricyclo [4.2.1.02,5]non-7-enes (tricyclononenes) and tricyclo[4.2.1.02,5]nona-3,7-dienes (tricyclonona-dienes)–norbornene type monomers containing norbornene and cyclobutane or cyclobutene fragments in the molecules. Their synthesis is carried out using available cyclopentadiene or quadricyclane, which is a product of norbornadiene photo-isomerization. The features of ring-opening metathesis and addition polymerization of tricyclononenes with participation of double bond in the norbornene fragment are highlighted. Examples of the polymerization of a wide range of tricyclononenes with F-, Si-, O-, and N-containing substituents have demonstrated that they are noticeably more active monomers than norbornenes with the same substituents. The main successes have been achieved in the synthesis of F- and Si-substituted polytricyclononenes, which are promising materials for lithography and membrane gas separation.

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REFERENCES

  1. Olefin Metathesis and Metathesis Polymerization, Ed. by K. J. Ivin and J. C. Mol (Acad. Press, San Diego, 1997).

    Google Scholar 

  2. Handbook of Metathesis, Ed. by R. H. Grubbs (Wiley-VCH, Weinheim, 2003), Vol. 3.

    Google Scholar 

  3. M. R. Buchmeiser, in Synthesis of Polymers: New Structures and Methods, Ed. by A. D. Schlüter, C. J. Hawker, and J. Sakamoto (Wiley, Weinheim, 2012).

    Google Scholar 

  4. Handbook of Metathesis, Ed. by R. H. Grubbs and E. Khosravi, 2nd ed. (Wiley-VCH, Weinheim, 2015), Vol. 3.

    Google Scholar 

  5. E. Finkelshtein, M. Gringolts, M. Bermeshev, P. Chapala, and Yu. Rogan, “Polynorbornenes,” in Membrane Materials for Gas and Vapor Separation Synthesis and Application of Silicon-Containing Polymers, Ed. by Yu. Yampolskii and E. Finkelshtein (Wiley, Chichester, 2017), p. 143.

    Google Scholar 

  6. K. L. Makovetskii, Polym. Sci., Ser. C 50, 22 (2008).

    Article  Google Scholar 

  7. F. Blank and C. Janiak, Coord. Chem. Rev. 253, 827 (2009).

    Article  CAS  Google Scholar 

  8. M. V. Bermeshev and P. P. Chapala, Prog. Polym. Sci. 84, 1 (2018).

    Article  CAS  Google Scholar 

  9. A. M. Polyakova, A. F. Platé, M. A. Pryanishnikova, and N. A. Lipatnikov, Pet. Chem. 1, 521 (1961).

    CAS  Google Scholar 

  10. J. P. Kennedy and H. S. Makowski, J. Macromol. Sci., Chem. 1, 345 (1967).

    Article  CAS  Google Scholar 

  11. N. G. Gaylord, B. M. Mandal, and M. Martan, J. Polym. Sci: Polym. Lett. Ed. 14, 555 (1976).

    CAS  Google Scholar 

  12. N. G. Gaylord and A. B. Deshpande, J. Polym. Sci.: Polym. Lett. Ed. 14, 613 (1976).

    CAS  Google Scholar 

  13. N. G. Gaylord, A. B. Deshpande, B. M. Mandal, and M. Martan, J. Macromol. Sci, Chem. 11, 1053 (1977).

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  15. I. F. A. F. El-Saafin and W. J. Feast, J. Mol. Catal. 15, 61 (1982).

    Article  CAS  Google Scholar 

  16. V. A. Petrov and N. V. Vasil’ev, Curr. Org. Synth. 3, 215 (2006).

    Article  CAS  Google Scholar 

  17. A. B. Alimuniar, J. H. Edwards, and W. J. Feast, J. Mol. Catal. 28, 313 (1985).

    Article  CAS  Google Scholar 

  18. R. S. Saunders, Macromolecules 28, 4347 (1995).

    Article  CAS  Google Scholar 

  19. P. P. Chapala, M. V. Bermeshev, L. E. Starannikova, I. L. Borisov, V. P. Shantarovich, V. G. Lakhtin, V. V. Volkov, and E. Sh. Finkelshtein, Macromol. Chem. Phys. 217, 1966 (2016).

    Article  CAS  Google Scholar 

  20. E. F. Connor, T. R. Younkin, J. I. Henderson, S. Hwang, R. H. Grubbs, W. P. Roberts, and J. J. Litzau, J. Polym. Sci., Part A: Polym. Chem. 40, 2842 (2002).

    Article  CAS  Google Scholar 

  21. A. E. Feiring, M.K. Crawford, W. B. Farnyam, R. H. French, K. W. Leffew, V. A. Petrov, F. L. Schadt, H. V. Tran, and F. C. Zumsteg, Macromolecules 39, 1443 (2006).

    Article  CAS  Google Scholar 

  22. H. V. Tran, R. J. Hung, T. Chiba, Sh. Yamada, T. Mrozek, Y.-T. Hsieh, C. R. Chambers, B. P. Osborn, B. C. Trinque, M. J. Pinnow, S. A. MacDonald, C. G. Willson, D. P. Sanders, E. F. Connor, R. H. Grubbs, and W. Conley, Macromolecules 35, 6539 (2002).

    Article  CAS  Google Scholar 

  23. D. P. Sanders, E. F. Connor, R. H. Grubbs, R. J. Hung, B. P. Osborn, T. Chiba, S. A. MacDonald, and C. G. Willson, Macromolecules 36, 1534 (2003).

    Article  CAS  Google Scholar 

  24. 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 

  25. 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 

  26. A. V. Syromolotov, M. V. Bermeshev, M. L. Gringolts, A. G. Kazmin, and E. S. Finkelshtein, Dokl. Chem. 437, 50 (2011).

    Article  CAS  Google Scholar 

  27. 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, 8055 (2015).

    Article  CAS  Google Scholar 

  28. V. R. Flid, M. L. Gringolts, R. S. Shamsiev, and E. Sh. Finkelshtein, Russ. Chem. Rev. 87, 1169 (2018).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. M. V. Bermeshev, A. V. Syromolotov, M. L. Gringolts, L. E. Starannikova, Y. P. Yampolskii, and E. S. Finkelshtein, Macromolecules 44, 6637 (2011).

    Article  CAS  Google Scholar 

  31. E. S. Finkelshtein, M. L. Gringolts, N. V. Ushakov, V. G. Lakhtin, S. A. Soloviev, and Y. P. Yampol’skii, Polymer 44, 2843 (2003).

    Article  CAS  Google Scholar 

  32. E. S. Finkelshtein, K. L. Makovetskii, M. L. Gringolts, Y. V. Rogan, T. G. Golenko, V. G. Lakhtin, and M. P. Filatova, J. Mol. Catal. A: Chem. 257, 9 (2006).

    Article  CAS  Google Scholar 

  33. M. L. Gringolts, M. V. Bermeshev, K. L. Makovetsky, and E. S. Finkelshtein, Eur. Polym. J. 45, 2142 (2009).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  35. P. Chapala, M. Bermeshev, L. Starannikova, V. Shantarovich, N. Gavrilova, V. Lakhtin, Yu. Yampolskii, and E. Finkelshtein, Macromol. Chem. Phys. 218, 1600385 (2017).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  37. N. Belov, Yu. Nizhegorodova, M. Bermeshev, and Yu.Yampolskii, J. Membr. Sci. 483, 136 (2015).

    Article  CAS  Google Scholar 

  38. D. Alentiev, E. Egorova, M. Bermeshev, L. Starannikova, M. Topchiy, A. F. Asachenko, P. Gribanov, M. S. Nechaev, Y. Yampolskii, and E. Finkelshtein, J. Mater. Chem. A 2018, 19393 (2018).

    Article  Google Scholar 

  39. D. A. Alentiev, S. A. Korchagina, E. S. Finkelshtein, M. S. Nechaev, A. F. Asachenko, M. A. Topchiy, P. S. Gribanov, and M. V. Bermeshev, Russ. Chem. Bull. 67, 121 (2018).

    Article  CAS  Google Scholar 

  40. D. A. Alentiev, D. M. Dzhaparidze, P. P. Chapala, M. V. Bermeshev, N. A. Belov, R. Yu. Nikiforov, L. E. Starannikova, Yu. P. Yampolskii, and E. Sh. Finkelshtein, Polym. Sci., Ser. B 60, 612 (2018).

    Article  CAS  Google Scholar 

  41. D. A. Alentiev, P. P. Chapala, M. P. Filatova, E. S. Finkelshtein, and M. V. Bermeshev, Mendeleev Commun. 26, 530 (2016).

    Article  CAS  Google Scholar 

  42. 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 

  43. 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 

  44. 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 

  45. M. Bermeshev, B. Bulgakov, L. Starannikova, G. Dibrov, P. Chapala, D. Demchuk, and Y. Yampolskii, J. Appl. Polym. Sci. 132, 41395 (2015).

    Article  CAS  Google Scholar 

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ACKNOWLWDGMENTS

This work was conducted within the framework of State Assignment for the Institute of Petrochemical Synthesis, Russian Academy of Sciences.

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Correspondence to E. Sh. Finkelshtein or P. P. Chapala.

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Finkelshtein, E.S., Chapala, P.P., Gringolts, M.L. et al. Polymerization of Tricyclononenes. Polym. Sci. Ser. C 61, 17–30 (2019). https://doi.org/10.1134/S1811238219010077

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