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Synthesis and spectral properties of 1,2,5-thiadiazolo-, 1,2,5-selenadiazolo-, and benzo-fused β-phenyl-substituted porphyrazines

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Abstract

Cross cyclotetramerization of trans-2,3-diphenylbutanedinitrile with 1,2,5-thia(selena)diazole-3,4-dicarbonitriles or phthalodinitrile in the presence of magnesium butoxide gave mixtures of Mg(II) porphyrazine complexes which were treated with trifluoroacetic acid to isolate unsymmetrical hexaphenyl-substituted 1,2,5-thia(selena)diazolo-and benzo-fused porphyrazines together with diphenyltribenzoporphyrazine. Their 1H NMR and electronic absorption spectra (in the UV and visible regions) were recorded. The effect of benzene and heteroring fusion on the electronic and steric structure and spectral properties of porphyrazine derivatives was studied in terms of the molecular orbital perturbation theory and semiempirical quantum-chemical calculations (AM1, PM3, ZINDO/S, CNDO/S).

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Authors and Affiliations

  1. Ivanovo State University of Chemical Technology, pr. F. Engel’sa 7, Ivanovo, 153460, Russia

    P. A. Stuzhin, I. V. Pimkov, A. Ul’-Khak, S. S. Ivanova & I. A. Popkova

  2. Institute of Molecular and Atomic Physics, National Academy of Belarus, Minsk, Belarus

    D. I. Volkovich & V. A. Kuz’mitskii

  3. Universita di Roma “La Sapienza”, Rome, Italy

    M. -P. Donzello

Authors
  1. P. A. Stuzhin
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  2. I. V. Pimkov
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  3. A. Ul’-Khak
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  4. S. S. Ivanova
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  5. I. A. Popkova
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  6. D. I. Volkovich
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  7. V. A. Kuz’mitskii
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  8. M. -P. Donzello
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Correspondence to P. A. Stuzhin.

Additional information

Original Russian Text © P.A. Stuzhin, I.V. Pimkov, A. Ul’-Khak, S.S. Ivanova, I.A. Popkova, D.I. Volkovich, V.A. Kuz’mitskii, M.-P. Donzello, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 12, pp. 1848–1857.

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Stuzhin, P.A., Pimkov, I.V., Ul’-Khak, A. et al. Synthesis and spectral properties of 1,2,5-thiadiazolo-, 1,2,5-selenadiazolo-, and benzo-fused β-phenyl-substituted porphyrazines. Russ J Org Chem 43, 1854–1863 (2007). https://doi.org/10.1134/S1070428007120202

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  • DOI: https://doi.org/10.1134/S1070428007120202

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