Abstract
Stable 2,7-diaminobenzopyrylium tetrafluoroborates were obtained by the successive treatment of 7-diethylaminocoumarin, 4-methyl-7-diethylaminocoumarin, and 9-methyl-1H,5H-quinolizino[9,9a,1-gh]coumarin with triethyloxonium tetrafluoroborate and amines, viz., diethylamine, piperidine, morpholine, benzylamine, and aniline. The spectral-luminescence characteristics of the synthesized compounds were investigated. The data from the 13C NMR spectra and x-ray diffraction analysis confirm the greater participation of the 2-amino group as compared with the 7-amino group in stabilization of the positive charge of the pyrylium system.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
M. A. KirpichËnok, S. K. Gorozhankin, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 6, 751 (1988).
M. Maeda, Laser Dyes, Academic Press, New York (1984).
S. K. Gorozhankin, M. A. KirpichËnok, N. A. Klyuev, and I. I. Grandberg, Izv. Timiryazev. Skh. Akad., No. 4, 151 (1986).
S. K. Gorozhankin, M. A. Kirpichenök, N. A. Klyuek, and V. G. Zhil'nikov, Izv. Timiryazev. Skh. Akad., No. 5, 181 (1987).
G. Hvistendahl, P. Gyorösi, and K. Undheim, Org.Mass Spectrom., 90, 80 (1974).
G. Jones, W. R. Jackson, Ch.-yoo Choi, and W. R. Bergmark, J. Phys. Chem., 89, 294 (1985).
A. T. Balaban, G. D. Mateescu, and M. Elian, Tetrahedron, 18, 1083 (1962).
M. A. Kirpichenok, I. I. Grandberg, L. K. Denisov, and L. M. Mel'nikova, Izv. Timiryazev. Skh. Akad., No. 3, 173 (1985).
M. A, Kirpichenök, D. S. Yufit, Yu. I. Struchkov, S. K. Gorozhankin, and I. I. Grandberg, Khim. Geterotskl. Soedin., No. 8, 1028 (1988).
B. I. Ionin, B. A. Ershov, and A. I. Kol'tov, NMR Spectroscopy in Organic Chemistry [in Russian], Khimiya, Leningrad (1983).
G. J. Martin, M. L. Martin, and S. Odiot, J. Org. Magn. Reson., 7, 2 (1975).
A. T. Balaban and V. Wray, J. Org. Magn. Reson., 9, 16 (1977).
M. Th. Chenon, S. Sib, and M. Simalty, J. Org. Magn. Reson., 12, 71 (1979).
J. C. Messager and Y. Delugeard, Cryst. Struct. Commun., 3, 391 (1974).
A. V. Goncharvo, D. S. Yufit, and Yu. T. Struchkov, Summaries of Papers Presented at the 5th All-Union Conference on Organic Crystal Chemistry [in Russian], Chernogolovka (1987), p. 86.
S. Parker, Photoluminescence of Solutions [Russian translation], Mir, Moscow (1972).
R. G. Gerr, A. I. Yanovskii, and Yu. T. Struchkov, Kristallografiya, 28, 1029 (1983).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 755–766, June, 1989.
Rights and permissions
About this article
Cite this article
KirpichËok, M.A., Gorozhankin, S.K., Yufit, D.S. et al. Synthesis and spectral-luminescence properties of 2,7-diaminobenzopyrylium tetrafluoroborates. Chem Heterocycl Compd 25, 621–631 (1989). https://doi.org/10.1007/BF00470018
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00470018