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
Olefin Metathesis and Metathesis Polymerization, Ed. by K. J. Ivin and J. C. Mol (Acad. Press, San Diego, 1997).
Handbook of Metathesis, Ed. by R. H. Grubbs (Wiley-VCH, Weinheim, 2003), Vol. 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).
Handbook of Metathesis, Ed. by R. H. Grubbs and E. Khosravi, 2nd ed. (Wiley-VCH, Weinheim, 2015), Vol. 3.
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.
K. L. Makovetskii, Polym. Sci., Ser. C 50, 22 (2008).
F. Blank and C. Janiak, Coord. Chem. Rev. 253, 827 (2009).
M. V. Bermeshev and P. P. Chapala, Prog. Polym. Sci. 84, 1 (2018).
A. M. Polyakova, A. F. Platé, M. A. Pryanishnikova, and N. A. Lipatnikov, Pet. Chem. 1, 521 (1961).
J. P. Kennedy and H. S. Makowski, J. Macromol. Sci., Chem. 1, 345 (1967).
N. G. Gaylord, B. M. Mandal, and M. Martan, J. Polym. Sci: Polym. Lett. Ed. 14, 555 (1976).
N. G. Gaylord and A. B. Deshpande, J. Polym. Sci.: Polym. Lett. Ed. 14, 613 (1976).
N. G. Gaylord, A. B. Deshpande, B. M. Mandal, and M. Martan, J. Macromol. Sci, Chem. 11, 1053 (1977).
E. S. Finkelshtein, M. V. Bermeshev, M. L. Gringolts, L. E. Starannikova, and Y. P. Yampolskii, Russ. Chem. Rev. 80, 341 (2011).
I. F. A. F. El-Saafin and W. J. Feast, J. Mol. Catal. 15, 61 (1982).
V. A. Petrov and N. V. Vasil’ev, Curr. Org. Synth. 3, 215 (2006).
A. B. Alimuniar, J. H. Edwards, and W. J. Feast, J. Mol. Catal. 28, 313 (1985).
R. S. Saunders, Macromolecules 28, 4347 (1995).
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).
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).
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).
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).
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).
M. V. Bermeshev, A. V. Syromolotov, M. L. Gringolts, V. G. Lakhtin, and E. S. Finkelshtein, Tetrahedron Lett. 52, 6091 (2011).
B. A. Bulgakov, M. V. Bermeshev, D. V. Demchuk, V. G. Lakhtin, A. G. Kazmin, and E. S. Finkelshtein, Tetrahedron 68, 2166 (2012).
A. V. Syromolotov, M. V. Bermeshev, M. L. Gringolts, A. G. Kazmin, and E. S. Finkelshtein, Dokl. Chem. 437, 50 (2011).
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).
V. R. Flid, M. L. Gringolts, R. S. Shamsiev, and E. Sh. Finkelshtein, Russ. Chem. Rev. 87, 1169 (2018).
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).
M. V. Bermeshev, A. V. Syromolotov, M. L. Gringolts, L. E. Starannikova, Y. P. Yampolskii, and E. S. Finkelshtein, Macromolecules 44, 6637 (2011).
E. S. Finkelshtein, M. L. Gringolts, N. V. Ushakov, V. G. Lakhtin, S. A. Soloviev, and Y. P. Yampol’skii, Polymer 44, 2843 (2003).
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).
M. L. Gringolts, M. V. Bermeshev, K. L. Makovetsky, and E. S. Finkelshtein, Eur. Polym. J. 45, 2142 (2009).
M. Gringolts, M. Bermeshev, Y. Yampolskii, L. Starannikova, V. Shantarovich, and E. Finkelshtein, Macromolecules 43, 7165 (2010).
P. Chapala, M. Bermeshev, L. Starannikova, V. Shantarovich, N. Gavrilova, V. Lakhtin, Yu. Yampolskii, and E. Finkelshtein, Macromol. Chem. Phys. 218, 1600385 (2017).
M. Bermeshev, B. Bulgakov, D. Demchuk, M. Filatova, L. Starannikova, and E. Finkelshtein, Polym. J. 45, 718 (2013).
N. Belov, Yu. Nizhegorodova, M. Bermeshev, and Yu.Yampolskii, J. Membr. Sci. 483, 136 (2015).
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).
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).
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).
D. A. Alentiev, P. P. Chapala, M. P. Filatova, E. S. Finkelshtein, and M. V. Bermeshev, Mendeleev Commun. 26, 530 (2016).
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).
I. L. Borisov, T. R. Akmalov, A. O. Ivanov, V. V. Volkov, E. S. Finkelshtein, and M. V. Bermeshev, Mendeleev Commun. 26, 124 (2016).
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).
M. Bermeshev, B. Bulgakov, L. Starannikova, G. Dibrov, P. Chapala, D. Demchuk, and Y. Yampolskii, J. Appl. Polym. Sci. 132, 41395 (2015).
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This work was conducted within the framework of State Assignment for the Institute of Petrochemical Synthesis, Russian Academy of Sciences.
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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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DOI: https://doi.org/10.1134/S1811238219010077