Abstract
The feasibility of using pyrene as a fluorescent probe in complexes cyclodextrin-pyrene-analyte in aqueous solutions was studied for several analytes (A) of different polarity. Bands that prove the formation of the complex Py2βCD were found for the first time in the UV-VIS spectrum of an aqueous solution of pyrene in the presence of β-cyclodextrin. A characteristic of a fluorescent probe is the ratio I 3/I 1 in the fluorescence spectrum, where I 3 is the intensity of the third vibronic line at ∼800 cm−1, and I 1 is the intensity of the 0-0 transition. The value of I 3/I 1 for Py2βCD is highly sensitive to the addition of an analyte with a concentration of several μM/L to the aqueous solution. Dependences of (I 3/I 1)/C on the function of the dielectric constant ɛ of the analyte fɛ= (ɛ − 1)/(2ɛ + 1) are divided into two straight lines with different slopes for nonpolar and polar solvents. Energies of insertion of analytes into Py2βCD were calculated by the quantumchemical PM3 method. An increase in (I 3/I 1)/C corresponds to the more thermodynamically stable complex 2APy2βCD.
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Kalyanasundaram, K. and Thomas, J.K., J. Am. Chem. Soc., 1977, vol. 99, no. 7, p. 2039.
Dong, D.C. and Winnik, M.A., Can. J. Chem., 1984, vol. 62, p. 2560.
Nakajima, A., Bull. Chem. Soc. Jpn., 1971, vol. 44, p 3272.
Avakyan, V.G., Nazarov, V.B., and Alfimov, M.V., Naphthalene: Structure, Properties and Applications, Antsyforov, G.I. and Ivanski, A.F., Eds., New York: Novapublishers, 2012, p. 127.
Munös de la Pena, A., Ndou, T., Zung, J.B., and Warner, I.M., J. Phys. Chem., 1991, vol. 95, p. 3330
Munoz de la Pena, A., Ndou, T., Zung, J.B., Greene, K.L., Live, D.H., and Warner, I.M., J. Am. Chem. Soc., 1991, vol. 113, p. 1572
Will, A.Y., Munoz de la Pena, A., Ndou, T., and Warner, I.M., Appl. Spectrosc., 1993, vol. 47, p. 277.
Nazarov, V.B., Avakyan, V.G., Vershinnikova, T.G., and Alfimov, M.V., Izv. Akad. Nauk, Ser. Khim., 2000, no, 10, p 1716
Avakyan, V.G., Nazarov, V.B., Alfimov, M.V., Voronezheva, N.I., and Bagatur’yants, A.A., Izv. Akad. Nauk, Ser. Khim., 2001, no. 2, p. 199.
Hamai, S., J. Phys. Chem., 1989, vol. 93, p. 2074.
Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, p. 6.
Szejtli, J., Cyclodextrins and Their Inclusion Complexes, Budapest: Akademiai Kiado, 1982.
Freidzon, A.Ya., Valiev, R.R., and Berezhnoy, A.A., RSC Adv., 2014, vol. 4, p. 42054.
Winkler, R.G., Fioravanti, S., Ciccotti, G., Margeritis, C., and Villa, M., J. Computer-Aided Mol. Design, 2000, vol. 14, p. 659.
Bakhshiev, N.G., Fotofizika dipol’-dipol’nykh vzaimodeistvii (Photophysics of Dipole-Dipole Interactions), St. Petersburg: Izd S.-Peterburgsk. Univ., 2005.
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Original Russian Text © V.G. Avakyan, V.B. Nazarov, A.V. Koshkin, M.V. Alfimov, 2015, published in Khimiya Vysokikh Energii, 2015, Vol. 49, No. 3, pp. 204–209.
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Avakyan, V.G., Nazarov, V.B., Koshkin, A.V. et al. Vibronic structure of electronic absorption and fluorescence spectra of pyrene in the complex with β-cyclodextrin in the presence of nonpolar and polar solvents. High Energy Chem 49, 177–182 (2015). https://doi.org/10.1134/S0018143915030030
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DOI: https://doi.org/10.1134/S0018143915030030