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Structure and photochromic properties of the crystalline 1,3-dimethyl-2-(3-phenylnorbornadienyl)benzimidazolium tetrafluoroborate

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Abstract

Molecular and crystal structures, as well as photochemistry in the solid state were studied for the norbornadiene, whose one double bond was modified by the simultaneous introduction of an electron-donating and electron-withdrawing substituents. Effects of the nature of substituents on the distance of the substituted C=C bond were analyzed by quantum chemical calculations.

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References

  1. A. D. Dubonosov, V. A. Bren, V. I. Minkin, in CRC Handbook of Organic Photochemistry and Photobiology, W. Horspool, F. Lenci, Eds, CRC Press, LLC, Boca Raton, Fla, 2004, p. 17/1.

    Google Scholar 

  2. A. D. Dubonosov, V. A. Bren, V. A. Chernoivanov, Usp. Khim., 2002, 71, 1040 [Russ. Chem. Rev. (Engl. Transl.), 2002, 71, 917].

    Google Scholar 

  3. C. D’Aniello, P. Musto, V. Venditto, G. Guerra, J. Mater. Chem., 2007, 17, 531.

    Article  Google Scholar 

  4. X. An, Y. Xie, Thermochim. Acta, 1993, 220, 17.

    Article  CAS  Google Scholar 

  5. V. A. Chernoivanov, A. D. Dubonosov, V. A. Bren, V. I. Minkin, S. V. Galichev, A. N. Suslov, Zh. Org. Khim., 1992, 28, 1647 [Russ. J. Org. Chem. (Engl. Transl.), 1992, 28].

    CAS  Google Scholar 

  6. V. A. Chernoivanov, A. D. Dubonosov, V. A. Bren, V. I. Minkin, A. N. Suslov, G. S. Borodkin, Mol. Cryst. Liq. Cryst., 1997, 297, 239.

    Article  CAS  Google Scholar 

  7. S. Bénard, E. Riviere, P. Yu, K. Nakatani, J. F. Delouis, Chem. Mater., 2001, 13, 159.

    Article  Google Scholar 

  8. S. M. Aldoshin, N. A. Sanina, V. I. Minkin, N. A. Voloshin, V. N. Ikorskii, V. I. Ovcharenko, V. A. Smirnov, N. K. Nagaeva, J. Mol. Struct., 2007, 826, 69.

    Article  CAS  Google Scholar 

  9. G. M. Sheldrick, SHELXTL v. 6.14, Structure Determination Software Suite, Bruker AXS, Madison (Wisconsin, USA), 2000.

    Google Scholar 

  10. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Stain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. C. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonazalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonazalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, GAUSSIAN 03, Revision D.01, Gaussian, Inc., Wallingford (CT), 2004.

    Google Scholar 

  11. S. M. Aldoshin, V. A. Bren, A. D. Dubonosov, O. A. Kozina, V. I. Minkin, V. A. Chernoivanov, Izv. Akad. Nauk, Ser. Khim., 1995, 504 [Russ. Chem. Bull. (Engl. Transl.), 1995, 44, 487].

    Google Scholar 

  12. V. M. Coiro, E. Giglio, F. Mazza, N. V. Pavel, J. Inclusion Phenom. Macrocyclic Chem., 1984, 1, 329.

    Article  CAS  Google Scholar 

  13. J. Benet-Buchholz, T. Haumann, R. Boese, Chem. Commun., 1998, 2003.

  14. E. Vessally, Zh. Fiz. Khim., 2009, 83, 930 [Russ. J. Phys. Chem. A (Engl. Transl.), 2009, 83, 809].

    Google Scholar 

  15. W. L. Dilling, Chem. Rev., 1966, 66, 373.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    E. A. Yurieva, V. V. Tkachev & S. M. Aldoshin

  2. Institute of Physical and Organic Chemistry at the Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov on Don, Russian Federation

    V. A. Chernoivanov, V. A. Bren & V. I. Minkin

Authors
  1. E. A. Yurieva
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  2. V. V. Tkachev
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  3. S. M. Aldoshin
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  4. V. A. Chernoivanov
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  5. V. A. Bren
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  6. V. I. Minkin
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Correspondence to E. A. Yurieva.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1386–1390, July, 2011.

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Yurieva, E.A., Tkachev, V.V., Aldoshin, S.M. et al. Structure and photochromic properties of the crystalline 1,3-dimethyl-2-(3-phenylnorbornadienyl)benzimidazolium tetrafluoroborate. Russ Chem Bull 60, 1409–1413 (2011). https://doi.org/10.1007/s11172-011-0211-y

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  • DOI: https://doi.org/10.1007/s11172-011-0211-y

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