Skip to main content

Influence of intermolecular hydrogen bonds on the luminescence properties of α-substituted cinnamonitriles


In view of the dramatic difference in the spectral-luminescence properties of α-(p-chlorobenzoyl)-4-diethylaminocinnamonitrile and α-ethoxycarbonyl-4-diethylaminocinnamonitrile in solutions and in the crystalline state, X-ray diffraction analysis has been applied to study crystals of these compounds. The intermolecular C-H...N and C-H...O hydrogen bonds are found to contribute to the quinoidization of molecules, which leads to a bathochromic shift in the absorption and fluorescence spectra. A spectral-luminescence study of the aforementioned compounds has revealed that the solvent temperature and polarity affect the position of absorption and luminescence peaks: a decrease in these parameters causes a hypsochromic shift.

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


  1. N. G. Bakhshiev, Spectroscopy of Intermolecular Interactions (Nauka, Moscow, 1972) [in Russian].

    Google Scholar 

  2. D. A. Drapkina, V. G. Brudz’, and B. M. Bolotin, Trudy IREA, No. 30, 333 (1967).

    Google Scholar 

  3. SAINT. Version 6.02A (Bruker AXS, Madison, WI, 2001).

  4. SHELXTL-Plus. Version 5.10 (Bruker AXS, Madison, WI, 1997).

  5. L. G. Kuz’mina, O. A. Fedorova, E. N. Andryukhina, et al., Kristallografiya 51(2), 299 (2006).

    Google Scholar 

  6. L. G. Kuz’mina, A. I. Vedernikov, N. A. Lobova, et al., Nucl. J. Chem. 31, 980 (2007).

    Article  Google Scholar 

  7. P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli, J. Am. Chem. Soc. 122, 10405 (2000).

    Article  Google Scholar 

  8. V. Bertolasi, P. Gilli, V. Ferreti, and G. Gilli, Acta Crystallogr. B 54, 50 (1998).

    Article  Google Scholar 

  9. Y. Mo, J. Mol. Model. 12, 665 (2006).

    Article  Google Scholar 

  10. R. Viswanathan, A. Asensio, and J. J. Dannenberg, J. Phys. Chem. A 108, 9205 (2004).

    Article  Google Scholar 

  11. A. Mohajeri, J. Mol. Struct.: THEOCHEM 678, 201 (2004).

    Article  Google Scholar 

  12. R. W. Gora, S. J. Grabowski, and J. Leszczynski, J. Phys. Chem. A 109, 6397 (2005).

    Article  Google Scholar 

  13. T. Steiner, Angew. Chem. Int. Ed. Engl. 41, 48 (2002).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to B. M. Bolotin.

Additional information

Original Russian Text © Ya.A. Mikhlina, B.M. Bolotin, B.M. Uzhinov, V.V. Volchkov, L.G. Kuz’mina, 2013, published in Kristallografiya, 2013, Vol. 58, No. 2, pp. 240–246.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Mikhlina, Y.A., Bolotin, B.M., Uzhinov, B.M. et al. Influence of intermolecular hydrogen bonds on the luminescence properties of α-substituted cinnamonitriles. Crystallogr. Rep. 58, 259–265 (2013).

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI:


  • Crystallography Report
  • Intermolecular Hydrogen Bond
  • Crystalline State
  • Ethoxycarbonyl
  • Chlorobenzoyl