Abstract
A new photochromic fulgimide, (E)-1-(anthracen-9-ylmethyl)-3-[1-(5-methoxy-2-methyl-1-phenyl-1H-benzo[g]indol-3-yl)ethylidene]-4-(propan-2-ylidene)pyrrolidine-2,5-dione, has been synthesized and found to exhibit fluorescence. The structure of this compound and intermediate fulgenates and amidofulgenic and fulgenic acids has been determined by electronic and vibrational spectroscopy, 1H and 13C NMR, and mass spectrometry. The amidofulgenic and fulgenic acids are capable of undergoing photoinduced reversible Z/E isomerization with respect to the C=C bond without subsequent cyclization, whereas fulgenates are converted to the corresponding cyclic structures. The new fluorescent fulgimide is transformed into the colored nonfluorescing cyclic isomer under UV irradiation. The reverse ring opening under visible light irradiation restores the fluorescence properties, which makes this compound a molecular fluorescence switch.
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Yokoyama, Y., Chem. Rev., 2000, vol. 100, p. 1717.
Yokoyama, Y., Gushiken, T., and Ubukata, T., Molecular Switches, Feringa, B.L. and Browne, W.R., Eds., Weinheim: Wiley, 2011, p. 81.
Bouas-Laurent, H. and Dürr, H., Pure Appl. Chem., 2001, vol. 73, p. 639.
Yokoyama, Y. and Kose, M., CRC Handbook of Organic Photochemistry and Photobiology, Horspool, W. and Lenci, F., Eds., Boca Raton: CRC, 2004, 2nd ed., p. 1.
Rueck-Braun, K., Mayer, K., Hebert, A., and Michalik, F., CRC Handbook of Organic Photochemistry and Photobiology, Griesbeck, A., Oelgemöller, M., and Ghetti, F., Eds., Boca Raton: Taylor & Francis, 2012, 3rd ed., p. 607.
Yokoyama, Y. and Kose, M., J. Photochem. Photobiol., A, 2004, vol. 166, p. 9.
Liang, Y.C., Dvornikov, A.S., and Rentzepis, P.M., Macromolecules, 2002, vol. 35, p. 9377.
Liang, Y.C., Dvornikov, A.S., and Rentzepis, P.M., Res. Chem. Intermed., 1998, vol. 24, p. 905.
Rybalkin, V.P., Pluzhnikova, S.Yu., Popova, L.L., Revinskii, Yu.V., Tikhomirova, K.S., Komissarova, O.A., Dubonosov, A.D., Bren, V.A., and Minkin, V.I., Mendeleev Commun., 2016, vol. 26, p. 21.
Yokoyama, Y., Tanaka, T., Yamane, T., and Kurita, Y., Chem. Lett., 1991, vol. 20, p. 1125.
Liang, Y.C., Dvornikov, A.S., and Rentzepis, P.M., Opt. Commun., 2003, vol. 223, p. 61.
Rybalkin, V.P., Shepelenko, E.N., Tkachev, V.V., Shilov, G.V., Balenko, S.K., Tsukanov, A.V., Popova, L.L., Dubonosov, A.D., Aldoshin, S.M., Bren’, V.A., and Minkin, V.I., Russ. Chem. Bull., Int. Ed., 2006, vol. 55, p. 101.
Balenko, S.K., Rybalkin, V.P., Makarova, N.I., Bezuglyi, S.O., Shepelenko, E.N., Popova, L.L., Tkachev, V.V., Aldoshin, S.M., Metelitsa, A.V., Bren’, V.A., and Minkin, V.I., Russ. Chem. Bull., Int. Ed., 2008, vol. 57, p. 1435.
Balenko, S.K., Makarova, N.I., Rybalkin, V.P., Shepelenko, E.N., Popova, L.L., Tkachev, V.V., Aldoshin, S.M., Metelitsa, A.V., Bren’, V.A., and Minkin, V.I., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, p. 954.
Rybalkin, V.P., Makarova, N.I., Pluzhnikova, S.Yu., Popova, L.L., Metelitsa, A.V., Bren’, V.A., and Minkin, V.I., Russ. Chem. Bull., Int. Ed., 2014, vol. 63, p. 1780.
Zmeeva, S.Yu., Rybalkin, V.P., Popova, L.L., Tkachev, V.V., Revinskii, Yu.V., Tikhomirova, K.S., Starikov, A.G., Dubonosov, A.D., Bren, V.A., Aldoshin, S.M., and Minkin, V.I., Tetrahedron, 2016, vol. 72, p. 5776.
Glaze, A.P., Harris, S.A., Heller, H.G., Johncock, W., Oliver, S.N., Strydom, P.J., and Whittall, J., J. Chem. Soc., Perkin Trans. 1, 1985, p. 957.
Bren’, V.A., Dubonosov, A.D., Minkin, V.I., Popova, L.L., Revinskii, Yu.V., Rybalkin, V.P., Tolpygin, I.E., Tsukanov, A.V., and Shepelenko, E.N., Russ. J. Org. Chem., 2002, vol. 38, p. 1813.
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Original Russian Text © V.P. Rybalkin, S.Yu. Zmeeva, L.L. Popova, K.S. Tikhomirova, Yu.V. Revinskii, A.D. Dubonosov, V.A. Bren’, V.I. Minkin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 1, pp. 36–41.
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Rybalkin, V.P., Zmeeva, S.Y., Popova, L.L. et al. Photochromic benzo[g]indolyl fulgimide with modulated fluorescence. Russ J Org Chem 53, 29–34 (2017). https://doi.org/10.1134/S1070428017010067
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DOI: https://doi.org/10.1134/S1070428017010067