Abstract
Novel crown-containing styryl dyes (CSD) based on 15-crown-5-substituted benzothiazole with various electron-donating groups in thepara-position of the benzene ring were synthesized. Spectral and photochemical properties ofcis- andtrans-isomers of CSD and their complexes with Mg2+ ions in solutions were studied. By analysis of spectral parameters and the magnitudes and directions of the shifts of absorption (fluorescence) maxima, the effects of substituents and complex formation on the photochromism of CSD were elucidated. Using quantum-chemical calculations, the possibility of controlling the degree of participation of either of the two chromophores in the long-wave electron transition by complex formation was analyzed.
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E. N. Ushakov, S. P. Gromov, O. A. Fedorova, and M. V. Alfimov,Izv. Akad. Nauk, Ser. Khim., 1997, 484 [Russ. Chem. Bull., 1997, 463 (Engl. Transl.)].
S. P. Gromov, M. V. Fomina, E. N. Ushakov, I. K. Lednev, and M. V. Alfimov,Dokl. Akad. Nauk SSSR, 1990,314, 1135 [Dokl. Chem., 1990 (Engl. Transl.)].
S. P. Gromov, M. V. Fomina, and M. V. Alfimov,Izv. Akad. Nauk, Ser. Khim., 1993, 1625 [Russ. Chem. Bull., 1993,42, 1561 (Engl. Transl.)].
S. P. Gromov, A. A. Golosov, O. A. Fedorova, D. E. Levin, and M. V. Alfimov,Izv. Akad. Nauk, Ser. Khim., 1995, 129 [Russ. Chem. Bull., 1995,44, 124 (Engl. Transl.)].
S. P. Gromov, O. A. Fedorova, M. V. Alfimov, S. I. Druzhinin, M. V. Rusalov, and B. M. Uzhinov,Izv. Akad. Nauk, Ser. Khim., 1995, 2003 [Russ. Chem. Bull., 1995,44, (Engl. Transl.)].
H. Hsu and Q. Lin,Huaxue Xuebao, 1982,10, 952.
R. Ungaro, B. El Haj, and J. Smid,J. Am. Chem. Soc., 1976,98, 5198.
H. Günther,NMR Spectroscopy. An Introduction, J. Wiley and Sons, New York, 1980, Ch. 2.
I. I. Baskin, K. Ya. Burshtein, A. A. Bagatur'yants, S. P. Gromov, and M. V. Alfimov,J. Mol. Struct., 1992,274, 93.
The Theory of the Photographic Process, Ed. T. H. James. Macmillan Publ., New York, 1977, Ch. 8.
J. Del Bene and H. H. Jaffe,J. Chem. Phys., 1968,48, 1807.
G. K. Klopman,Chem. Phys. Lett., 1967,1, 200.
B. M. Bolotin and B. M. Krasovitskii.Organicheskie lyuninofory [Organic Luminophors], Khimiya, Moscow, 1984, 334 pp. (in Russian).
C. A. Parker,Photoluminescence of Solutions, Elsevier, Amsterdam, 1968, Ch. 3.
P. I. Voskresenskii,Tekhnika laboratornykh rabot [Laboratory Procedures], Khimiya, Moscow, 1969, 720 pp. (in Russian).
E. N. Ushakov, Ph. D. (Chem.) Thesis, Institute of Chemical Physics in Chernogolovka of the RAS, Chernogolovka, 1995, 47 (in Russian).
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For Part 19, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 999–1006, May, 1997.
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Gromov, S.P., Levin, D.E., Burshtein, K.Y. et al. Crown-ether styryl dyes. Russ Chem Bull 46, 959–966 (1997). https://doi.org/10.1007/BF02496128
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DOI: https://doi.org/10.1007/BF02496128