Abstract
Spironaphthoxazines linked with aza-15(18)-crown-5(6) fragments were synthesized and studied for the first time. Addition of alkaline-earth cations to solutions of crown-containing spironaphthoxazines causes a hypsochromic shift of the absorption band of the spiro form and a bathochromic shift of the absorption band of the merocyanine form, shifts the equilibrium to the merocyanine form, and changes the lifetime of the photoexcited merocyanine form. The spectral and kinetic data were used to propose a mechanism of complexation and calculate the stability constants of the resulting complexes. The complexation involves the crown fragment and the merocyanine oxygen atom. The type of the complex is determined by the cation nature and size.
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O. A. Fedorova, S. P. Gromov, Yu. P. Strokach, Yu. V. Pershina, S. A. Sergeeva, V. A. Barachevsky, G. Pepe, A. Samat, R. Guglielmetti, and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 1999, 1974 [Russ. Chem. Bull., 1999, 48, 1950 (Engl. Transl.)].
R. C. Bertelson, Photochromism, Techniques in Chemistry, Ed. G. H. Brown, Wiley Interscience, New York, 1971, 3, 45.
R. Guglielmetti, in Photochromism-Molecules and Systems, Studies in Organic Chemistry, Eds. H. Durr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990, 40, 314.
V. A. Barachevsky, in Spektroskopiya fotoprevrashchenii v molekulakh [Spectroscopy of Phototransformations in Molecules], Ed. A. A. Krasnovskii, Nauka, Leningrad, 1977, 182 (in Russian).
L. Cazaux, M. Faher, A. Lopez, C. Picard, and P. Tisnes, J. Photochem. Photobiol. A: Chem., 1994, 77, 217.
J. Bourson, F. Badaoui, and B. Valear, J. Fluorescence, 1994, 4, 275.
A. P. de Silva and S. K. R. A. Sandanayake, Angew. Chem., Int. Ed. Engl., 1990, 29, 1173.
S. Das, G. K. Thomas, K. Y. Thomas, P. V. Kamat, and M. V. George, J. Phys. Chem., 1994, 98, 9291.
S. P. Gromov and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 1997, 641 [Russ. Chem. Bull., 1997, 46, 611 (Engl. Transl.)].
M. Inouye, M. Ueno, K. Tsuchiya, N. Nakayama, T. Konishi, and T. Kitao, J. Org. Chem., 1992, 57, 5377.
B. F. Nazarov, B. F. Soldatenkova, M. V. Alfimov, P. Lareginie, A. Samat, and R. Guglielmetti, Izv. Akad. Nauk, Ser. Khim., 1996, 2220 [Russ. Chem. Bull., 1996, 45, 2105 (Engl. Transl.)].
O. A. Fedorova, S. P. Gromov, Yu. V. Pershina, S. A. Sergeev, Yu. P. Strokach, V. A. Barachevsky, M. V. Alfimov, G. Pepe, A. Samat, and R. Guglielmetti, J. Chem. Soc., Perkin Trans. 2, 2000, 563.
M. Rickwood, S. D. Marsden, M. E. Ormsby, A. L. Staunton, D. W. Wood, J. D. Hepworth, and C. D. Gabbut, Mol. Cryst. Liq. Cryst., 1994, 246, 17.
Yu. P. Strokach, T. M. Valova, V. A. Barachevsky, M. V. Alfimov, V. Lokshin, A. Samat, and R. Guglielmetti, Zh. Nauchn. Prikl. Fotograf., 1999, 44, 1 (in Russian).
J. Bourson, J. Pouget, and B. Valeur, J. Phys. Chem., 1993, 97, 4552.
Handbook of Chemistry and Physics, Ed. R. C. Weast, 66th ed., CRC Press, Boca Raton, 1985, F-164.
Host-Guest Complex Chemistry. Macrocycles, Synthesis, Structures, Applications, Eds. F. Vögtle and E. Weber, Springer, Berlin, 1985.
R. L. Zaichenko, F. V. Lyubimov, V. S. Marevtsev, and M. I. Cherkashin, Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 1040 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 37, No. 10 (Engl. Transl.)].
J. W. Zhou, Y. T. Li, and X. Q. Song, J. Photochem. Photobiol. A: Chem., 1995, 87, 37.
H. Ono and C. Osada, Fuji Photo Film Co., Ltd, Ger. Offen. 1, 954, 220 (Cl. C 07d), May, 1970, Jpn.; Chem. Abstr., 1970, 73, 26617p.
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Strokach, Y.P., Fedorova, O.A., Gromov, S.P. et al. Crown-containing spironaphthoxazines and spiropyrans. 2. Influence of metal cations on the photochromic properties of spironaphthoxazines linked with aza-15(18)-crown-5(6) ethers. Russian Chemical Bulletin 51, 58–66 (2002). https://doi.org/10.1023/A:1015001527963
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DOI: https://doi.org/10.1023/A:1015001527963