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Polymerization of 1,4-bis[2-(N-vinyl)pyrrolyl]benzene

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Abstract

Polymers of 1,4-bis[2-(N-vinyl)pyrrolyl]benzene with free N-vinyl groups in side chains are synthesized in the presence of AIBN (2–5 wt %, 70°C) with a yield of up to 34% and a molecular mass of up to 11.5 × 103. In the presence of cationic catalysts (Me3SiCl, the LiBF4-dimethoxyethane system, and BF3 · OEt2), 1,4-bis[2-(N-vinyl)pyrrolyl]benzene gives macromolecules with alternating 1,2-pyrrolene and ethylidene units in the backbone with yields of 80, 44, and 33%, respectively. The polymers demonstrate paramagnetic and luminescent properties.

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References

  1. B. A. Trofimov, in The Chemistry of Heterocyclic Compounds, Ed. by R. A. Jones (Wiley, New York, 1992), p. 131.

    Chapter  Google Scholar 

  2. J. R. Reynolds, A. R. Katrizky, J. Soloducho, et al., Macromolecules 27, 7225 (1994).

    Article  CAS  Google Scholar 

  3. J. Soloducho, Synth. Met. 99, 181 (1999).

    Article  CAS  Google Scholar 

  4. B. A. Trofimov, A. M. Vasil’tsov, E. Yu. Schmidt, et al., Eur. J. Org. Chem. 2005, 4338 (2005).

    Article  Google Scholar 

  5. J. Herbick, M. Kijak, A. Zieliska, et al., J. Phys. Chem., A 106, 2158 (2002).

    Article  Google Scholar 

  6. C.-Y. Wu, M.-S. Chen, C.-A. Lin, et al., Chem.-Eur. J. 12, 2263 (2006).

    Article  CAS  Google Scholar 

  7. C. Pozo-Gonzalo, J. A. Pomposo, J. Rodriguez, et al., Synth. Met. 157, 60 (2007).

    Article  CAS  Google Scholar 

  8. F. Lucchesini, Tetrahedron 48, 9951 (1992).

    Article  CAS  Google Scholar 

  9. A. M. Vasil’tsov, E. Yu. Schmidt, A. I. Mikhaleva, et al., Tetrahedron 61, 7756 (2005).

    Article  Google Scholar 

  10. I. K. Petrushenko, V. I. Smirnov, K. B. Petrushenko, et al., Zh. Obshch. Khim. 77, 1307 (2007).

    Google Scholar 

  11. A. Gossauer, Pyrrole. In: Methoden der Organische Chemie, (Georg Thieme Verlag, Stuttgart, 1994), Vol. 1, p. 556.

    Google Scholar 

  12. R. J. Tedeschi, in Encyclopedia of Physical Science and Technology, Ed. by R. A. Meyers (Academic, San Diego, 2004), Vol. 1, p. 55.

    Google Scholar 

  13. S. E. Korostova and A. I. Mikhaleva, Zh. Org. Khim. 18, 2620 (1982).

    CAS  Google Scholar 

  14. B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles (Nauka, Novosibirsk, 1984) [in Russian].

    Google Scholar 

  15. C. Poole, Electron Spin Resonance: A Comprehensive Treatise on Experimental Techniques (Wiley, New York, 1967; Mir, Moscow, 1970).

    Google Scholar 

  16. A. Weissberger, E. Proskauer, J. Riddick, and E. Toops, Organic Solvents. Physical Properties and Methods of Purification (Wiley, New York, 1955; Inostrannaya literatura, Moscow, 1958).

    Google Scholar 

  17. B. A. Trofimov, L. V. Morozova, I. V. Tatarinova, et al., Polymer Science, Ser. B 44, 291 (2002) [Vysokomol. Soedin., Ser. B 44, 2048 (2002)].

    Google Scholar 

  18. B. A. Trofimov, A. I. Mikhaleva, and L. V. Morozova, Usp. Khim. 54, 1034 (1985).

    CAS  Google Scholar 

  19. B. A. Trofimov, M. V. Markova, L. V. Morozova, et al., Polymer Science, Ser. B 49, 292 (2007) [Vysokomol. Soedin., Ser. B 49, 2200 (2007)].

    Article  Google Scholar 

  20. O. V. Petrova, M. V. Markova, L. N. Sobenina, et al., Izv. Akad. Nauk, Ser. Khim., No. 1, 115 (2009).

  21. Physical Methods in Chemistry of Heterocyclic Compounds, Ed. by A. R. Katritskii (Khimiya, Moscow, 1966) [in Russian].

    Google Scholar 

  22. Atlas of Spectra of Aromatic and Heteroaromatic Compounds, Ed. by V. A. Koptyug (Inst. Org. Khim., Sib. Otd., Akad. Nauk SSSR, Novosibirsk, 1981) [in Russian].

    Google Scholar 

  23. B. A. Trofimov, L. V. Morozova, M. V. Sigalov, et al., Makromol. Chem. 188, 2251 (1987).

    Article  CAS  Google Scholar 

  24. L. V. Morozova, A. I. Mikhaleva, M. V. Markova, et al., Izv. Akad. Nauk, Ser. Khim., No. 2, 423 (1996).

  25. B. A. Trofimov, M. V. Markova, L. V. Morozova, and A. I. Mikhaleva, Arkivoc P(ix), p. 24 (2001).

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Correspondence to L. V. Morozova.

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Original Russian Text © B.A. Trofimov, M.V. Markova, L.V. Morozova, A.I. Mikhaleva, E.Yu. Shmidt, N.V. Zorina, Sang Heon Hyun, 2010, published in Russian in Vysokomolekulyarnye Soedineniya, Ser. B, 2010, Vol. 52, No. 4, pp. 662–666.

This work was supported by the Russian Foundation for Basic Research (project no. 09-03-12037-ofi-m).

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Trofimov, B.A., Markova, M.V., Morozova, L.V. et al. Polymerization of 1,4-bis[2-(N-vinyl)pyrrolyl]benzene. Polym. Sci. Ser. B 52, 193–197 (2010). https://doi.org/10.1134/S1560090410030097

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  • DOI: https://doi.org/10.1134/S1560090410030097

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