Russian Journal of Organic Chemistry

, Volume 49, Issue 6, pp 913–921 | Cite as

Synthesis, acid-base properties, and deselenation of 5,6,8,9,11,12-hexakis(4-tert-butylphenyl)[1,2,5]selenadiazolo[3,4-b]porphyrazine



Cross cyclotetramerization of bis(4-tert-butylphenyl)fumaronitrile with 1,2,5-selenadiazole-3,4-dicarbonitrile in the presence of magnesium butoxide as template afforded a mixture of magnesium(II) porphyrazine complexes, from which magnesium complex of 5,6,8,9,11,12-hexakis(4-tert-butylphenyl)[1,2,5]selenadiazolo[3,4-b]porphyrazine was isolated by column chromatography and was subjected to demetalation on treatment with trifluoroacetic acid. The free ligand was found to undergo protonation at one meso-nitrogen atom in acid medium and deprotonation of one pyrrole ring to form monoanion by the action of bases. Reductive deselenation of the title compound with formation of vicinal diamino porphyrazine was studied by spectral and kinetic methods, and a mechanism involving two hydrosulfide ions was proposed.


Hydrogen Sulfide Electronic Absorption Spectrum Azine Spectrophotometric Titration Porphyrazine 
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  1. 1.
    Haman, S., Hietschol, M., Mrwa, A., Müller, M., Starke, M., and Kilper, R., Molecular Electronics. Materials and Methods, Lazarev, P.I., Ed., Dordrecht: Springer Science+Business Media, 1991, p. 129.Google Scholar
  2. 2.
    Wöhrle, D., Schnurpfeil, G., Makarov, S.G., Kazarin, A., and Suvorova, O.N., Macroheterocycles, 2012, vol. 5, p. 191.CrossRefGoogle Scholar
  3. 3.
    De la Torre, G., Vazquez, P., Agullo-Lopez, F., and Torres, T., J. Mater. Chem., 1998, vol. 8, p. 1671.CrossRefGoogle Scholar
  4. 4.
    Sternberg, E., Dolphin, D., and Brucker, C., Tetrahedron, 1998, vol. 54, p. 4151.CrossRefGoogle Scholar
  5. 5.
    Lukyanets, E.A., J. Porphyrins Phthalocyanines, 1999, vol. 3, p. 424.CrossRefGoogle Scholar
  6. 6.
    Zhou, R., Josse, F., Goepel, W., Ozturk, Z.Z., and Bekaroglu, O., Appl. Organomet. Chem., 1996, vol. 10, p. 557.CrossRefGoogle Scholar
  7. 7.
    Sorokin, A.B. and Kudrik, E.V., Catal. Today, 2011, vol. 159, p. 37.CrossRefGoogle Scholar
  8. 8.
    Mack, J. and Kobayashi, N., Chem. Rev., 2011, vol. 111, p. 281.CrossRefGoogle Scholar
  9. 9.
    Stuzhin, P.A. and Ercolani, C., The Porphyrin Handbook, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., San Diego: Academic, 2003, vol. 15, p. 263.Google Scholar
  10. 10.
    Donzello, M.P., Ercolani, C., and Stuzhin, P.A., Coord. Chem. Rev., 2006, vol. 250, p. 1530.CrossRefGoogle Scholar
  11. 11.
    Miyoshi, Y., Fujimoto, T., Yoshikawa, H., Matsushita, M.M., Awaga, K., Yamada, T., and Ito, H., Org. Electronics, 2011, vol. 12, p. 239.CrossRefGoogle Scholar
  12. 12.
    Stuzhin, P.A., Mikhailov, M.S., Yurina, E.S., Bazanov, M.I., Koifman, O.I., Pakhomov, G.L., Travkin, V.V., and Sinelshchikova, A.A., Chem. Commun., 2012, vol. 48, p. 10 135.CrossRefGoogle Scholar
  13. 13.
    Stuzhin, P.A., Mikhailov, M.S., Travkin, V.V., Gudkov, E.Y., and Pakhomov, G.L., Macroheterocycles, 2012, vol. 5, p. 162.CrossRefGoogle Scholar
  14. 14.
    Kudrik, E.V., Bauer, E.M., Ercolani, C., Chiesi-Villa, A., Rizzoli, C., Gaberkorn, A., and Stuzhin, P.A., Mendeleev Commun., 2001, p. 43.Google Scholar
  15. 15.
    Stuzhin, P.A., Pimkov, I.V., Ul’-Khak, A., Ivanova, S.S., Popkova, I.A., Volkovich, D.I., Kuz’mitskii, V.A., and Donzello, M.-P., Russ. J. Org. Chem., 2007, vol. 43, p. 1854.CrossRefGoogle Scholar
  16. 16.
    Knyukshto, V.N., Volkovich, D.I., Gladkov, L.L., Kuz’mitskii, V.A., Ul’-Khak, A., Popkova, I.A., Stuzhin, P.A., and Solov’ev, K.N., Opt. Spektrosk., 2012, vol. 113, p. 401.CrossRefGoogle Scholar
  17. 17.
    Solovyov, K.N., Stuzhin, P.A., Kuzmitskiy, V.A., Volkovich, D.I., Knyukshto, V.N., Borisevich, E.A., and Ul-Haque, A., Macroheterocycles, 2010, vol. 3, p. 51.Google Scholar
  18. 18.
    Baum, S.M., Trabanco, A.A., Montalban, A.G., Micallef, A.S., Zhong, C., Meunier, H.G., Suhling, K., Phillips, D., White, A.J.P., Williams, D.J., Barrett, A.G.M., and Hoffman, B.M., J. Org. Chem., 2003, vol. 68, p. 1665.CrossRefGoogle Scholar
  19. 19.
    Bauer, E.M., Ercolani, C., Galli, P., Popkova, I.A., and Stuzhin, P.A., J. Porphyrins Phthalocyanines, 1999, vol. 3, p. 371.CrossRefGoogle Scholar
  20. 20.
    Ul-Haq, A., Donzello, M.P., and Stuzhin, P.A., Mendeleev Commun., 2007, vol. 17, p. 337.CrossRefGoogle Scholar
  21. 21.
    Ul-Haq, A. and Stuzhin, P.A., Macroheterocycles, 2008, vol. 1, p. 82.Google Scholar
  22. 22.
    Zhao, M., Stern, C., Barrett, A.G.M., and Hoffman, B.M., Angew. Chem., Int. Ed., 2003, vol. 42, p. 462.CrossRefGoogle Scholar
  23. 23.
    Zhao, M., Zhong, C., Stern, C., Barrett, A.G.M., and Hoffman, B.M., J. Am. Chem. Soc., 2005, vol. 127, p. 9769.CrossRefGoogle Scholar
  24. 24.
    Baumann, T.F., Barrett, A.G.M., and Hoffman, B.M., Inorg. Chem., 1997, vol. 36, p. 5661.CrossRefGoogle Scholar
  25. 25.
    Marinina, L.E., Mikhalenko, S.A., and Luk’yanets, E.A., Zh. Obshch. Khim., 1973, vol. 43, p. 2025.Google Scholar
  26. 26.
    Gaberkorn, A.A., Donzello, M.-P., and Stuzhin, P.A., Russ. J. Org. Chem., 2006, vol. 42, p. 929.CrossRefGoogle Scholar
  27. 27.
    Berezin, B.D., Stuzhin, P.A., and Khelevina, O.G., Khim. Geterotsikl. Soedin., 1986, vol. 22, p. 1677.Google Scholar
  28. 28.
    Stuzhin, P.A., Khelevina, O.G., and Berezin, B.D., Phthalocyanines: Properties and Applications, Leznoff, C.C. and Lever, A.B.P., Eds., Weinheim: VCH, 1996, vol. 4, p. 19.Google Scholar
  29. 29.
    Khelevina, O.G., Rumyantseva, S.V., Chizhova, N.V., Stuzhin, P.A., and Migalova, I.S., Russ. J. Gen. Chem., 2003, vol. 73, p. 478.CrossRefGoogle Scholar
  30. 30.
    Stuzhin, P.A., Ivanova, Yu.B., Migalova, I.S., and Sheinin, V.B., Russ. J. Gen. Chem., 2005, vol. 75, p. 1300.CrossRefGoogle Scholar
  31. 31.
    Khelevina, O.G., Bubnova, A.S., Makarova, O.N., Lukina, S.A., Vagin, S.I., and Stuzhin, P.A., Koord. Khim., 2006, vol. 32, no. 6, p. 468.Google Scholar
  32. 32.
    Pesin, V.G., Usp. Khim., 1970, vol. 39, p. 1950.CrossRefGoogle Scholar
  33. 33.
    Montalban, A.G., Lange, S.J., Beall, L.S., Mani, N.S., Williams, D.J., White, A.J.P., Barrett, A.G.M., and Hoffman, B.M., J. Org. Chem., 1997, 62, p. 9284.CrossRefGoogle Scholar
  34. 34.
    Montalban, A.G., Meunier, H.G., Ostler, R.B., Barrett, A.G.M., Hoffman, B.M., and Rumbles, G., J. Phys. Chem., 1999, vol. 103, p. 4352.CrossRefGoogle Scholar
  35. 35.
    Suturina, E.A., Semenov, N.A., Lonchakov, A.V., Bagryanskaya, I.Yu., Gatilov, Y.V., Irtegova, I.G., Vasilieva, N.V., Lork, E., Mews, R., Gritsan, N.P., and Zibarev, A.V., J. Phys. Chem., 2011, vol. 115, p. 4851.CrossRefGoogle Scholar

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© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  1. 1.Ivanovo State University of Chemistry and TechnologyIvanovoRussia

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