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Regioselective bromination of (Tetraphenyltetrabenzoporphyrinato)palladium(II). Synthesis of a new octabromo derivative of the tetraphenyltetrabenzoporphyrin series

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Abstract

Bromination of (meso-tetraphenyltetrabenzoporphyrinato)palladium(II) with bromine in the presence of tetramethylammonium bromide occurs exclusively at the benzene rings fused to the porphyrin system while the phenyl rings in the meso positions are not involved. The corresponding octabromo-substituted complex was obtained using a large excess of bromine on prolonged reaction time. The complex was isolated and characterized by 1H NMR spectra, electronic absorption spectra in the UV and visible regions, and MALDI-TOF mass spectra. It was assigned the structure of symmetric (22,23,72,73,122,123,172,173-octabromo-5,10,15,20-tetraphenyltetrabenzoporphyrinato)palladium(II).

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References

  1. Vinogradov, S.A., Lo, L.-W., Jenkins, W.T., Evans, S.M., Koch, C., and Wilson, D.F., Biophys. J., 1996, vol. 70, no. 4, p. 1609.

    Article  CAS  Google Scholar 

  2. Wilson, D.F., Lee, W.M.F., Makonnen, S., Finikova, O., Apreleva, S., and Vinogradov, S.A., J. Appl. Physiol., 2006, vol. 101, no. 6, p. 1648.

    Article  CAS  Google Scholar 

  3. Shea, P.B., Kanicki, J., Cao, Y., and Ono, N., Appl. Phys. Lett., 2005, vol. 87, no. 17, p. 1.

    Article  CAS  Google Scholar 

  4. Shea, P.B., Kanicki, J., and Ono, N., J. Appl. Phys., 2005, vol. 98, no. 1, 014 503.

  5. Shea, P.B., Kanicki, J., Pattison, L.R., Petroff, P., Kawano, M., Yamada, H., and Ono, N., J. Appl. Phys., 2006, vol. 100, no. 3, 034 502.

  6. Galanin, N.E., Kudrik, E.V., and Shaposhnikov, G.P., Russ. J. Org. Chem., 2001, vol. 37, no. 5, p. 687.

    Article  CAS  Google Scholar 

  7. Kopranenkov, V.N., Dashkevich, S.N., and Luk’yanets, E.A., Zh. Obshch. Khim., 1981, vol. 51, no. 11, p. 2513.

    CAS  Google Scholar 

  8. Kopranenkov, V.N., Makarova, E.A., and Luk’yanets, E.A., Zh. Obshch. Khim., 1981, vol. 51, no. 12, p. 2727.

    CAS  Google Scholar 

  9. Finikova, O., Cheprakov, A., Beletskaya, I., and Vinogradov, S., Chem. Commun., 2001, no. 3, p. 261.

  10. Finikova, O.S., Cheprakov, A.V., Beletskaya, I.P., Carroll, P.J., and Vinogradov, S.A., J. Org. Chem., 2004, vol. 69, no. 2, p. 522.

    Article  CAS  Google Scholar 

  11. Vicente, M.G.H., Tome, A.C., Walter, A., and Cavaleiro, J.A.S., Tetrahedron Lett., 1997, vol. 38, no. 20, p. 3639.

    Article  CAS  Google Scholar 

  12. Ito, S., Ochi, N., Murashima, T., Uno, H., and Ono, N., Heterocycles, 2000, vol. 52, no. 1, p. 399.

    CAS  Google Scholar 

  13. Uno, H., Ishikawa, T., Hoshi, T., and Ono, N., Tetrahedron Lett., 2003, vol. 44, no. 28, p. 5163.

    Article  CAS  Google Scholar 

  14. Khoroshutin, A.V., Vinogradov, S.A., and Wilson, D.F., ACS National Meeting, Dallas, US, 1998.

  15. Fischer, H. and Halbig, P., Justus Liebig’s Ann. Chem., 1926, vol. 450, no. 1, p. 151.

    Article  CAS  Google Scholar 

  16. Tse, M.K., Zhou, Z.Y., Mak, T.C.W., and Chan, K.S., Tetrahedron, 2000, vol. 56, no. 39, p. 7779.

    Article  CAS  Google Scholar 

  17. Shanmugathasan, S., Johnson, C.K., Edwards, C., Matthews, E.K., Dolphin, D., and Boyle, R.W., J. Porphyrins Phthalocyanines, 2000, vol. 4, no. 3, p. 228.

    Article  CAS  Google Scholar 

  18. Zhou, X.A., Tse, M.K., Wan, T.S.M., and Chan, K.S., J. Org. Chem., 1996, vol. 61, no. 11, p. 3590.

    Article  CAS  Google Scholar 

  19. DiMagno, S.G., Lin, V.S.Y., and Therien, M.J., J. Org. Chem., 1993, vol. 58, no. 22, p. 5983.

    Article  CAS  Google Scholar 

  20. D’souza, F., Vllard, A., Van Caemelbecke, E., Franzen, M., Boschi, T., Tagliatesta, P., and Kadish, K.M., Inorg. Chem., 1993, vol. 32, no. 19, p. 4042.

    Article  CAS  Google Scholar 

  21. Bhyrappa, P. and Krishnan, V., Inorg. Chem., 1991, vol. 30, no. 2, p. 239.

    Article  CAS  Google Scholar 

  22. Hoffmann, P., Labat, G., Robert, A., and Meunier, B., Tetrahedron Lett., 1990, vol. 31, no. 14, p. 1991.

    Article  CAS  Google Scholar 

  23. Nudy, L.R., Hutchinson, H.G., and Schieber, C., Tetrahedron, 1984, vol. 40, no. 12, p. 2359.

    Article  CAS  Google Scholar 

  24. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.

    Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1/3, Moscow, 119992, Russia

    A. V. Khoroshutin & A. V. Anisimov

  2. Moscow State Textile University, Moscow, Russia

    D. E. Chumakov & K. I. Kobrakov

Authors
  1. A. V. Khoroshutin
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  2. D. E. Chumakov
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  3. A. V. Anisimov
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  4. K. I. Kobrakov
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Correspondence to A. V. Khoroshutin.

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Original Russian Text © A.V. Khoroshutin, D.E. Chumakov, A.V. Anisimov, K.I. Kobrakov, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 11, pp. 1909–1914.

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Khoroshutin, A.V., Chumakov, D.E., Anisimov, A.V. et al. Regioselective bromination of (Tetraphenyltetrabenzoporphyrinato)palladium(II). Synthesis of a new octabromo derivative of the tetraphenyltetrabenzoporphyrin series. Russ J Gen Chem 77, 1959–1964 (2007). https://doi.org/10.1134/S1070363207110205

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  • DOI: https://doi.org/10.1134/S1070363207110205

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