Abstract
It was demonstrated by means of the IR and PMR spectra that 1-phenyl-3,5-diaryl-2-pyrazolines that contain a grouping with a strong electron-acceptor effect, viz. a 4-nitrophenyl or 4-naphthalanhydride group or a 1,8-naphthoylene-1′,2′-benzimidazole fragment, in the 3 position undergo Vilsmeier formylation, like unsubstituted 1,3,5-triphenyl-2-pyrazoline, in the para position of the 1-phenyl ring. An investigation of the spectral-luminescence properties of the synthesized 1-(4′-formylphenyl)-3,5-diaryl-2-pyrazolines showed that the introduction in the 1-phenyl ring of an electron-acceptor aldehyde group, which is inferior with respect to its acceptor effect to the groupings in the 3 position of the heteroring, does not change the nature of the long-wave absorption band. Substantial hypsochromic and hypsofluoric effects as compared with the corresponding 1-phenyl-unsubstituted compounds are noted in the electronic spectra of these compounds.
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L. A. Kutulya, A. E. Shevchenko, and Yu. N. Surov, Khim. Geterotsikl. Soedin., No. 2, 250 (1975).
L. A. Kutulya, A. E. Shevchenko, T. P. Zubanova, and D. G. Pereyaslova, in: Scinttllators and Organic Luminophores [in Russian], Vol. 3, Kharkov (1974), p. 8.
L. A. Kutulya and A. E. Shevchenko, USSR Inventor's Certificate No. 717046; Byull Izobret., No. 7 (1980).
S. V. Tsukerman, E. G. Buryakovskaya, Yu. S. Rozum, and V. F. Lavrushin, Zh. Prikl. Spektrosk., 8, 453 (1968).
A. Hassner and M. J. Michelson, J. Org. Chem., 27, 3974 (1963).
R. Sustmann, R. Huisgen, and H. Huber, Chem. Ber., 100, 1802 (1967).
F. Pragst, H. Köppel, W. Jugelt, and F. G. Weber, J. Electroanal. Chem., 60, 323 (1975).
E. G. Buryakovskaya, Author's Abstract of Master's Dissertation, Kharkov (1970).
E. E. Baroni and K. A. Kovyrzina, Zh. Obshch. Khim., 33, 959 (1963).
Toshihiko Kimura, Yasushi Kai, Noritake Yasuoka, and Nobutami Kasai, Acta Crystallogr., B33, 1786 (1977).
S. V. Tsukerman, E. G. Buryakovskaya, and V. F. Lavrushin, Opt. Spektrosk., 26, 541 (1969).
L. M. Kutsyna, L. V. Voevoda, V. G. Tishchenko, and A. V. Shepel', Opt. Spektrosk., 26, 168 (1969).
É. A. Shevchenko, Author's Abstract of Master's Dissertation, Moscow (1970).
L. A. Kutulya, V. F. Morina, A. E. Shevchenko, and Yu. N. Surov, Zh. Prtkl. Spektrosk., 27, 76 (1977).
L. A. Kutulya, Yu. N. Surov, A. E. Shevchenko, and V. F. Lavrushin, Reakts. Sposobn. Org. Soedin., Tartu, 15, 464 (1978).
B. M. Krasovitskii, L. A. Kutulya, A. E. Shevchenko, L. D. Pchelinova, and L. I. Bogdanova, USSR Inventor's Certificate No. 825523; Byull. Izobret., No. 16 (1981).
R. N. Nurmukhametov, Absorption and Luminescence of Aromatic Compounds [in Russian], Khimiya, Moscow (1971), p. 185.
B. M. Krasovitskii and B. M. Bolotin, Organic Luminophores [in Russian], Khimiya, Leningrad (1976).
G. F. Slez'ko, Author's Abstract of Master's Dissertation, Kharkov (1971).
B. M. Krasovitskii and É. A. Shevchenko, Khim. Geterotsikl. Soedin., No. 4, 756 (1968).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 807–811, June, 1982.
The authors thank I. D. Kalikhman for recording the PMR spectra.
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Kutulya, L.A., Shevchenko, A.E. & Pchelinova, L.D. Synthesis and spectral-luminescence properties of 1-(4′-formylphenyl)-3,5-diaryl-2-pyrazolines. Chem Heterocycl Compd 18, 612–615 (1982). https://doi.org/10.1007/BF00506155
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DOI: https://doi.org/10.1007/BF00506155