Abstract
Spectral and photochemical properties of 1-(9-anthryl)-2-(2-quinolyl)ethylene (9A2QE) in neutral and protonated forms have been studied experimentally and by quantum-chemical methods. It has been found that the quantum yield of trans-cis photoisomerization (φtc) has values of φtc < 0.5 typical of the diabatic photoisomerization for both forms of 9A2QE. A comparison of this data with the results of the study of other aza-diarylethylenes containing the 2-styrylquinoline (2SQ) moiety has led to the general conclusion that the increase in the π-system in 2SQ upon fusion of the benzene rings results in the disappearance of the α-effect, which lies in the fact that the quantum yield increases upon going from the neutral to protonated form up to the values φtc > 0.5, which exceeds the limiting value for the diabatic photoisomerization.
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Lee, Y.J., Whitten, D.G., and Pederson, L., J. Am. Chem. Soc., 1971, vol. 93, p. 6330.
Shin, E.J., Stackow, R., and Foote, C.S., Phys. Chem. Chem. Phys., 2002, vol. 4, p. 5088.
Baraldi, I., Spalletti, A., and Vanossi, D., Spectrochim. Acta A, 2003, vol. 59, p. 75.
Ginocchietti, G., Mazzucato, U., and Spalletti, A., Int. J. Photoenergy, 2004, vol. 6, p. 241.
Ciorba, S., Bartocci, G., Galiazzo, G., Mazzucato, U., and Spalletti, A., J. Photochem. Photobiol., A: Chem., 2008, vol. 195, p. 301.
Ciorba, S., Fontana, F., Ciancaleoni, G., Caronna, T., Mazzucato, U., and Spalletti, A., J. Fluoresc., 2009, vol. 19, p. 759.
Galiazzo, G., Bortolus, P., and Gennari, G., Gazz. Chim. Ital., 1990, vol. 120, p. 581.
Budyka, M.F., Potashova, N.I., Gavrishova, T.N., and Li, V.M., High Energy Chem., 2008, vol. 42, p. 446.
Spalletti, A., Mazzucato, U., Aloisi, G.G., and Pannacci, D., Z. Phys. Chem. Neue Folge, 1983, vol. 138, p. 199.
Budyka, M.F., Russ. Chem. Rev., 2012, vol. 81, p. 477.
Budyka, M.F., Potashova, N.I., Chashchikhin, O.V., Gavrishova, T.N., and Lee, V.M., High Energy Chem., 2011, vol. 45, p. 492.
Budyka, M.F., Li, V.M., and Potashova, N.I., High Energy Chem., 2013, vol. 47, p. 107.
Shin, E.J., Bull. Korean Chem. Soc., 1999, vol. 20, p. 1263.
Li, V.M., Gavrishova, T.N., and Budyka, M.F., Russ. J. Org. Chem., 2012, vol. 48, p. 823.
Becker, H.D., Chem. Rev., 1993, vol. 93, p. 145.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., et al., Gaussian 03, Revision D.01, Wallingford: Gaussian, 2004.
Fischer, E., J. Phys. Chem., 1967, vol. 71, p. 3704.
Budyka, M.F., Potashova, N.I., Gavrishova, T.N., and Li, V.M., High Energy Chem., 2012, vol. 46, p. 309.
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Original Russian Text © M.F. Budyka, N.I. Potashova, T.N. Gavrishova, V.M. Li, 2014, published in Khimiya Vysokikh Energii, 2014, Vol. 48, No. 3, pp. 224–229.
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Budyka, M.F., Potashova, N.I., Gavrishova, T.N. et al. Photochemical properties of 1-(9-Anthryl)-2-(2-Quinolyl)ethylene. High Energy Chem 48, 185–190 (2014). https://doi.org/10.1134/S0018143914030047
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DOI: https://doi.org/10.1134/S0018143914030047