Abstract
Squarylium dyes based on isomeric di(tert-butyl)methyl-substituted pyrylium, thiopyrylium, and benzopyrylium salts have been synthesized. The dye containing 4, 6-di(tert-butyl)pyrylium residues was converted to its analog with methylpyridinium residues. The PMR and electronic absorption spectra of the dyes obtained were investigated. It was established that deepening of the color from dicarbocyanines to squaraines is characteristic only of dyes containing heterocyclic residues with high or medium electron-donor capacity. For dyes containing heterocyclic residues with low electron-donor capacity the opposite pattern is observed.
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References
M. A. Kudinova, E. I. Maiboroda, Yu. L. Slominskö, and Khim. Geterotsikl. Soedin., No. 1, 96 (1996).
J. Fabian, H. Nakazumi, and M. Matsuoka, Chem. Rev.,92, 1197 (1992).
K.-Y. Law, Chem. Rev.,93, 449 (1993).
M. Emmelius, G. Pavloski, and H. Vollmann, Angew. Chem. Int. Ed. Engl.,28, 1445 (1989).
M. Matsuoka, Infrared Absorption Dyes, Plenum Press, New York (1990).
T. N. Geraimova and V. V. Shelkovnikov, Usp. Khim., No. 6, 102 (1992).
M. R. Derry and B. Henne, Heterocycles,35, 1149 (1993).
S. Yasui, M. Matsuoka, and T. Kitao, Dyes and Pigments,10, 13 (1988).
V. V. Kudryukov, A. A. Ishchenko, M. A. Kudinova, and A. I. Tohuachev, Khim. Geterotsikl. Soedin., No. 7, 760 (1987).
W A. Kudinova, V. V. Kudryukov, A. A. Ishchenko, and A. I. Tolmnachev, Khim. Geterotsikl. Soedin., No. 7, 902 (1990).
M. A. Kudinova, V. V. Kurdynkov, A. A. Ishchenko, and A. I. Tolmachev, Khim. Geterotsikl. Soedin., No. 3, 339 (1992).
H. E. Sprenger and W. Ziegenbein, Angew Chem.,79, 581 (1967).
Japanese Paten No. 58,220,143; Chem. Abstr,101, ,219727a(1984).
Japanese Patent No. 63,168,393; Chem. Abstr.,110, 125550a (1989).
H. Nakazumi, K. Natukawa, K. Nakai, and K. Isagawa, Angew Chem. Int. Ed. Engl.,33, 1001 (1994).
N. Kuramoto, K. Natsukawa, and K. Asao, Dyes and Pigments,11, 21 (1989).
A. T. Balaban, G. D. Mateescu, and M. Elian Tetrahedron,18, 1083 (1962).
V. G. Kharchenko M. E. Stankevich, A. R. Yakoreva, and A. A. Rasadova, Khim. Geterotsikl. Soedin., No. 7, 916 (1972).
Y. Kobayash, V. Gato, and M. Kurahash, Bull. Chem. Soc. Jpn,59, 311 (1986).
D. Keil, H. Hartmann, and T. Moschny, Dyes and Pigments,17, 19 (1991).
K. Law, F. C. Bailey, and L. J. Bluett, Canud. J Chem.,64, 1608 (1986).
S. Das, K. G. Thomas, O. Ranmmahan M. V. George, and P. V. Kamat, J. Phys. Chem.,51, 1362 (1993)
A. D. Kachkovskii, Structure and Color of Polymethine Dyes [in Russian], Kiev, Naukova Dumka (1989).
R. W. Bigelow and H. J. Freund, J. Chem. Phys.,107, 159 (1986).
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Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, 253660. Translated from Khimiya Geterotsklicheskikh Soedinenii, No. 8, pp. 1038–1044, August, 1996. Original article submitted May 8, 1996.
For communication 34, see [1].
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Kurdyukov, V.V., Kudinova, M.A. & Tolmachev, A.I. Pyrylocyanines. 35. Squarylium dyes based on tert-butyl-substituted pyrylium and thiopyrylium salts. Chem Heterocycl Compd 32, 891–896 (1996). https://doi.org/10.1007/BF01176962
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DOI: https://doi.org/10.1007/BF01176962