Skip to main content

Crystalline and molecular design of functionalized viologens


The regularities of molecular and crystalline structure of functionalized (including mesoionic) viologens were systematically studied. For this purpose a number of fundamentally new viologenic systems was synthesized containing functional groups in side substituents. As a result of extensive X-ray structural studies it is revealed that unlike “classical” viologens, which in crystal form cation-anion pairs or cation-anion stacks, functionalized viologens are bound into endless chains by means of strong intermolecular hydrogen bonds.

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


  1. Monk, P.M.S., The Viologens. Chichester; New York; England: Wiley, 1998, and references therein.

    Google Scholar 

  2. Imai, Y., Kido Sh., Kamon, K., Kinuta, T., Sato, T., Tajami, N., Kuroda, R., and Mastubara, Y., Org. Lett., 2007, vol. 9, no. 24, p. 5047.

    Article  CAS  Google Scholar 

  3. Imai, Y., Kinuta, T., Sato, T., Tajami, N., Kuroda, R., Matubara, Y., and Yoshida, Z., Tetr. Lett., 2006, vol. 47, no. 21, p. 3603.

    Article  CAS  Google Scholar 

  4. Asakawa, M., Brown, C.L., Pasini, D., Stoddart, J.F., and Wyatt, P.G., J. Org. Chem., 1996, vol. 61, no. 21, p. 7234.

    Article  CAS  Google Scholar 

  5. Garcia, M.E., Gavin, E.A., Deng, N., Andrievski, A.A., and Mallouk, T.E., Tetr. Lett., 1996, vol. 37, no. 46, p. 8313.

    Article  CAS  Google Scholar 

  6. Garcia, M.E., Gavin, E.A., Benesi, A.J., and Mallouk, T.E., J. Org. Chem., 1998, vol. 63, no. 22, p. 7663.

    Article  Google Scholar 

  7. Gunter, M.J., Jeynes, T.P., Johnston, M.R., and Turner, P., Zh. Chen. J. Chem. Soc., Perkin Trans., 1, 1998, no. 12, p. 1945.

  8. Suzuki, M., Waraksa, C.C., Nakayama, H., Hanabusa, K., and Kimura, M., Chem. Commun., 2001, vol. 19, p. 2012.

    Article  Google Scholar 

  9. Polishchuk, Yu.I., Grineva, L.G., Polishchuk, A.P., and Chernega, A.N., Zh. Obshch. Khim., 1997, vol. 67, no. 11, p. 1893.

    Google Scholar 

  10. Polishchuk, Yu.I., Grineva, L.G., Polishchuk, A.P., and Chernega, A.N., Zh. Obshch. Khim., 1998, vol. 68, no. 4, p. 647.

    Google Scholar 

  11. Sakai, K., Ikuta, Y., Shiomi, M., Tamane, T., Tomita, Y., Tsubomura, T., and Nemoto, N., Acta Cryst. C, 1997, vol. 53, p. 331.

    Article  Google Scholar 

  12. Vermeulen, L.A. and Robinson, P.D., Acta Cryst. C, 1996, vol. 52, p. 984.

    Article  Google Scholar 

  13. Robinson, P.D., Smith, K.R., and Vermeulen, L.A., Acta Cryst. C, 2002, vol. 58, p. 632.

    Article  Google Scholar 

  14. Gutov, A.V., Rusanov, E.B., Egorov, O.A., and Gernega, A.N., Zh. Org. Farm. Khim., 2008, vol. 6, no. 4, p. 46.

    CAS  Google Scholar 

  15. Kuleshova, L.N. and Zorkii, P.M., Acta Cryst. B, 1981, vol. 37, no. 7, p. 1363.

    Article  Google Scholar 

  16. Polishchuk, Yu.I., Grineva, L.G., Polishchuk, A.P., and Chernega, A.N., Zh. Obsch. Khim., 1996, vol. 66, no. 9, p. 1530.

    CAS  Google Scholar 

  17. Shimizu, N., Wu, W., Kohara, A., Kohda, K., Suzuki, T., Kawazoe, Y., Biological & Pharmaceutical Bulletin., 1997, vol. 20, no. 2, p. 168.

    CAS  Google Scholar 

  18. Hyung, K., Kim, D., and Han, S., New Journal of Chemistry, 2005, vol. 29, no. 8, p. 1022.

    Article  CAS  Google Scholar 

  19. Polishchuk, I.Yu., Cand. Sci. (Chem.) Dissertation, 1997.

  20. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuse-ria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A. Jr, Vreven, T., Kudin, K.N., Burant, J.C., Millam, M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannen-berg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 98, Gaussian, Inc., Pittsburgh PA, 2001.

    Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to A. V. Gutov.

Additional information

Original Russian Text © A.V. Gutov, E.B. Rusanov, A.B. Ryabitskii, I.F. Tsimbal, A.N. Chernega, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 9, pp. 1553–1561.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Gutov, A.V., Rusanov, E.B., Ryabitskii, A.B. et al. Crystalline and molecular design of functionalized viologens. Russ J Gen Chem 79, 1910 (2009).

Download citation

  • Received:

  • Published:

  • DOI:


  • General Chemistry
  • Torsion Angle
  • Bipyridine
  • Pyridine Ring
  • Carboxy Group