Abstract
Spectral and luminescent properties of novel derivatives of 2,4,5-triphenylimidazole synthesized in this study have been investigated in different solvents. For solutions of azomethine-substituted hydroxytriphenylimidazole (I) and two structural isomers, hydroxy-meta-bisimidazoles III and IV differing in the position of the OH group, two luminescence bands due to the presence of two ground-state conformers are observed. The equilibrium between the two conformers depends on the structure of the molecule and the solvent. For solutions of III and IV in polar and nonpolar solvents and for I in nonpolar solvents, long-wave-length luminescence dominates from the conformer with possibility of intramolecular proton transfer in the excited state. For I in protic and highly polar solvents, short-wavelength luminescence is the main one; depending on the excitation wavelength, it is possible to detect weak long-wavelength (green) or more intense short-wavelength (blue) luminescence.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Kulhanek, J. and Filip, B., Beilstein J. Org. Chem., 2012, vol. 8, p. 25.
Danco, M., Yrdlovie, P., and Kulhanek, J., J. Fluoresc., 2011, vol. 21, p. 1779.
Fridman, N., Kaftory, M., Eichen, Y., and Speiser, S., J. Mol. Struct., 2009, vol. 917, p. 101.
Fridman, N., Kaftory, M., and Speiser, S., Sens. Actuators B, 2007, vol. 126, p. 107.
Fridman, N., Speiser, S., and Kaftory, M., Crystal Growth Design, 2006, vol. 6, no. 7, p. 1653.
Song, G.-L., Zhu, H.-J., Chen, L., Liu, S., and Luo, Z.-H., Helv. Chim. Acta, 2010, vol. 93, p. 2397.
Park, S., Kwon, J.E., and Park, S.Y., Phys. Chem. Chem. Phys., 2012, vol. 14, p. 8878.
Sakai, K.-I., Ishikawa, T., and Akutagawa, T., J. Mater. Chem. C, 2013, vol. 1, p. 7866.
Krasovitskii, V.M. and Bolotin, B.M., Organicheskie lyuminofory (Organic Luminophores), Moscow Khimiya, 1984.
Vargas, V. and Amigo, L., J. Chem. Soc., Perkin Trans., 2001, vol. 2, p. 1124.
Shienok, A.I., Kol’tsova, L.S., Zaichenko, N.L., and Marevtsev, V.S., Izv. Akad. Nauk, Ser. Khim., 2002, no. 11, p. 1894.
Gostev, F.E., Koltsova, L.S., Petrukhin, A.N., Titov, A.A., Shiyonok, A.I, Zaichenko, N.L., Marevtsev, V.S., and Sarkisov, O.M., J. Photochem. Photobiol., A, 2003, vol. 156, p. 15.
Rodembusch, F.S., Buckup, T., Segala, M., Tavares, L., Correia, R.R.B., and Stefani, V., Chem. Phys., 2004, vol. 305, p. 115.
Jayabharathi, J., Thanikachalam, V., Srinivasan, N., and Saravanan, K., J. Fluoresc., 2011, vol. 21, p. 595.
Davidson, D., Weiss, M., and Jelling, M., Org. Chem., 1937-1938, vol. 2, p. 319.
Parker, C.A., Photoluminescence of Solutions, Amsterdam Elsevier, 1968.
Padalkar, V.S., Ramasami, P., and Sekar, N., J. Fluoresc., 2013, vol. 23, p. 839.
Sun, W., Li, S., Hu, R., Qian, Y., Wang, S., and Yang, G., J. Phys. Chem. A, 2009, vol. 113, p. 5888.
Houri, Y., Charaf-Eddin, Y., Laurent, A.D., Massue, J., Ziessel, R., Ulrich, G., and Jacquemin, D., Phys. Chem. Chem. Phys., 2014, vol. 16, p. 1319.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © I.R. Mardaleishvili, A.V. Lyubimov, N.L. Zaichenko, L.S. Kol’tsova, A.I. Shienok, A.S. Tatikolov, 2016, published in Khimiya Vysokikh Energii, 2016, Vol. 50, No. 4, pp. 286–293.
Rights and permissions
About this article
Cite this article
Mardaleishvili, I.R., Lyubimov, A.V., Zaichenko, N.L. et al. Luminescence of new hydroxy-2,4,5-triarylimidazoles with an intramolecular hydrogen bond. High Energy Chem 50, 274–280 (2016). https://doi.org/10.1134/S0018143916040123
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0018143916040123