Abstract
The syntheses of aryl-substituted octaaza analogs of phthalocyanine — tetra-2,3-(4,5-diphenylpyrazino)porphyrazin and its vanadyl complex — and also of the vanadyl complex of tetra-2,3-(4-phenylquinolino)porphyrazin — a tetraaza analog of naphthalocyanine — are described. A modified singlestage method for the synthesis of the previously reported tetra-2,3-(5-tert-butylpyrazino)porphyrazin is put forward. The electronic absorption spectra of the compounds synthesized have been studied in organic solvents and acid media — in sulfuric acid solution and in organic solvents with the addition of phenol or trichloroacetic acid.
Similar content being viewed by others
References
G. Reinert, G. Hoelze, and G. Graf, Ger. Offen. 3518804; Chem. Abs., 105, 25830 (1986).
C. Ward, USA Pat. 4069138; Chem. Abs., 89, 113740 (1978).
V. E. Maizlish, A. B. Korzhenevskii, and V. N. Klyuev, Khim. Geterotsikl. Soedin., No. 9, 1257 (1984).
A. A. Tanaka, C. Fierro, D. A. Scherson, and E. Yaeger, Materials Chem. Phys., 22, No. 3/4, 431 (1989).
M. Yamana, N. Kashiwazaki, M. Yamamoto, and T. Nakano, Jpn. J. Appl. Phys. 26, No. 7, 1113 (1987).
D. Schlettwein, D. Worhle, and N. J. Jaeger, J. Electrochem. Soc., 136, No. 10, 2882 (1989).
T. Murayama, Sh. Maeda, and Y. Kurose, Jpn. Pat. 61291187; Chem. Abs., 107, 68274 (1987).
M. G. Gal'pern and E. A. Luk'yanets, Zh. Obshch. Khim., 39, No. 11, 2536 (1969).
W. Freyer, Z. Chem., 26, No. 6, 217 (1986).
M. G. Gal'pern and E. A. Luk'yanets, Khim. Geterotsikl. Soedin., No. 6, 858 (1972).
E. A. Luk'yanets (ed.), Electronic Spectra of Phthalocyanines and Related Compounds [in Russian], Izd. NIITÉKhIM, Cherkassy (1989), p. 73.
S. Tokita, N. Kai, M. Osa, T. Ohkoshi, M. Kojima, and H. Nishi, Chemistry of Functional Dyes: Ist International Symposium, Osaka (1989), p. 46.
M. Hanack and R. Thies, Chem. Ber., 121, No. 7, 1225 (1988).
A. Bernhard, P. Neumann, and R.-D. Kohler, Ger. Offen. 3829851; Chem. Abs., 114, 91997 (1989).
S. A. Mikhailenko and E. A. Luk'yanets, Zh. Obshch. Khim., 39, No. 9, 2129 (1969).
G. I. Goncharova, M. G. Gal'pern, and E. A. Luk'yanets, Zh. Obshch. Khim., 57, No. 666 (1987).
G. I. Goncharova, M. G. Gal'pern, and E. A. Luk'yanets, Abstracts of Reports at the IIIrd All-Union Conference on the Chemistry and Biochemistry of Porphyrins [in Russian], Samarkand (1982), p. 25.
E. G. Gal'pern, E. A. Luk'yanets, and M. G. Gal'pern, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1976 (1973).
T. Enokida and Sh. Ehashi, Chem. Lett., No. 2, 179 (1988).
H. W. Rothkopf, D. Wohrle, R. Muller, and G. Kopmehl, Chem. Ber., 108, 875 (1975).
J. G. Farbenind, Brit. Pat. 471418; Chem. Abs., 32, 1479 (1938).
E. C. Taylor and H. D. Heindel, J. Org. Chem., 32, No. 5, 1668 (1967).
S. A. Mikhailenko, L. A. Yagodina, and E. A. Luk'yanets, Zh. Obshch. Khim., 26, No. 7, 1598 (1976).
S. V. Vul'fson, O. L. Lebedev, and E. A. Luk'yanets, Zh. Prikl. Spektrosk., 17, No. 5, 903 (1972).
M. G. Gal'pern and E. A. Luk'yanets, Zh. Obshch. Khim., 41, No. 11, 2549 (1971).
A. S. Akopov, V. V. Bykova, and B. D. Berezin, Zh. Org. Khim., 19, No. 3, 581 (1983).
I. V. Surov, A. S. Akopov, and B. D. Berezin, Koordinats. Khim., 12, No. 1, 72 (1986).
B. D. Berezin, V. N. Klyuev, and A. B. Korzhenevskii, Izv. Vyssh. Uchebn. Zaved, Khim. Khim. Tekhnol., 20, No. 3, 357 (1977).
S. S. Iodko, O. L. Kaliya, M. G. Gal'pern, V. N. Kopranenkov, O. L. Lebedev, and E. A. Luk'yanets, Koordinats. Khim., 8, No. 8, 1025 (1982).
R. C. Fuson, H. Gray, and J. J. Gouza, J. Am. Chem. Soc., 61, 1937 (1939).
Ad. Claus and C. Nicolaysen, Chem. Ber., 18, 27006 (1885).
E. A. Fehnel, J. G. Dyrup, and M. B. Davidson, J. Org. Chem., 23, 1996 (1958).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 58–63, January, 1993.
Rights and permissions
About this article
Cite this article
Gal'pern, M.G., Kudrevich, S.V. & Novozhilova, I.G. Synthesis and spectroscopic properties of soluble aza analogs of phthalocyanine and naphthalocyanine. Chem Heterocycl Compd 29, 49–54 (1993). https://doi.org/10.1007/BF00528635
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00528635