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.
Buy single article
Instant access to the full article PDF.
Price excludes VAT (USA)
Tax calculation will be finalised during checkout.
N. G. Bakhshiev, Spectroscopy of Intermolecular Interactions (Nauka, Moscow, 1972) [in Russian].
D. A. Drapkina, V. G. Brudz’, and B. M. Bolotin, Trudy IREA, No. 30, 333 (1967).
SAINT. Version 6.02A (Bruker AXS, Madison, WI, 2001).
SHELXTL-Plus. Version 5.10 (Bruker AXS, Madison, WI, 1997).
L. G. Kuz’mina, O. A. Fedorova, E. N. Andryukhina, et al., Kristallografiya 51(2), 299 (2006).
L. G. Kuz’mina, A. I. Vedernikov, N. A. Lobova, et al., Nucl. J. Chem. 31, 980 (2007).
P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli, J. Am. Chem. Soc. 122, 10405 (2000).
V. Bertolasi, P. Gilli, V. Ferreti, and G. Gilli, Acta Crystallogr. B 54, 50 (1998).
Y. Mo, J. Mol. Model. 12, 665 (2006).
R. Viswanathan, A. Asensio, and J. J. Dannenberg, J. Phys. Chem. A 108, 9205 (2004).
A. Mohajeri, J. Mol. Struct.: THEOCHEM 678, 201 (2004).
R. W. Gora, S. J. Grabowski, and J. Leszczynski, J. Phys. Chem. A 109, 6397 (2005).
T. Steiner, Angew. Chem. Int. Ed. Engl. 41, 48 (2002).
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
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). https://doi.org/10.1134/S106377451302017X
- Crystallography Report
- Intermolecular Hydrogen Bond
- Crystalline State