Skip to main content

Halogenation of metalloporphyrins


We found that thionyl chloride can chlorinate porphyrin complexes with transient metals (Pd, Ni, or Cu) at the free β andmeso-positions of the porphyrin macrocycle. A more prolonged or rigorous treatment also causes the chlorination of side alkyl substituents, mainly, methyl groups.

This is a preview of subscription content, access via your institution.


  1. Nastri, F., Lombardi, A., D’Andrea, L.D., D’Agostino, B., Falciani, M., Rossi, F., Pavone, V., and Filipelli, A.,Biopolymers (Peptide Science), 1998, vol. 47, pp. 5–22.

    Article  CAS  Google Scholar 

  2. Roberts, W.G. and Smith, K.M.,Photochem. Photobiol., 1989, vol. 49, pp. 431–438.

    PubMed  CAS  Google Scholar 

  3. Akhlynina, T.V., Jans, D.A., Rosenkranz, A.A., Statsyuk, N.V., Balashova, I.Y., Pavo, I., Rubin, A.B., and Sobolev, A.S.,J. Biol. Chem., 1997, vol. 272, pp. 20 328–20 331.

    Article  CAS  Google Scholar 

  4. Eastwood, D. and Gouterman, M.,J. Mol. Spektrosc., 1970, vol. 35, pp. 359–375.

    Article  CAS  Google Scholar 

  5. Kravitskii, B.M. and Bolotik, B.M.,Organicheskie lyuminofory (Organic Luminophores), Moscow: Khimiya, 1984.

    Google Scholar 

  6. Proshina, E.Yu., Osin, N.S., Rumyantseva, V.D., and Mironov, A.F., RF Patent 1 707 539, 1993.

  7. Papkovsky, D.B.,Sens. Actuators, B, 1993, vol. 11, pp. 293–300.

    Article  Google Scholar 

  8. Papkovsky, D.B., Desyaterik, J.V., Ponomarev, G.V., Kurochkin, I.N., and Korpela, T.,Anal. Chim. Acta, 1995, vol. 310, pp. 233–239.

    Article  CAS  Google Scholar 

  9. Vanderkooi, J., Maniara, G., Green, T.J., and Wilson, D.F.,J. Biol. Chem., 1987, vol. 262, pp. 5476–5482.

    PubMed  CAS  Google Scholar 

  10. Khalil, G.E., Gouterman, M.P., and Green, E., US Patent 4 810 655, 1989.

  11. Ponamoreva, O.N., Rumyantseva, V.D., Mironov, A.F., and Chudinov, A.V.,Bioorg. Khim., 1995, vol. 21, pp. 296–300.

    CAS  Google Scholar 

  12. Ponamoreva, O.N., Synthesis of Phosphorescing Markers on the Basis of Metalloporphyrins,Cand. Sci. (Chem.) Dissertation, Moscow: Lomonosov State Academy of Fine Chemical Technology, 1995, p. 44.

    Google Scholar 

  13. Robic, N., Bied-Charreton, C., Perree-Fauvet, M., Verchere-Beaur, C., Salmon, L., and Gaudemer, A.,Tetrahedron Lett., 1990, vol. 31, pp. 4739–4742.

    Article  CAS  Google Scholar 

  14. Ivasita, Yu., Jpn. Patent 53-112900, cl. 16 E64 (S07D487/22),R. Zh. Khim., 1980, vol. 3, p. 30247P.

  15. Mironov, A.F., Rumyantseva, V.D., and Ponamoreva, O.N.,Mendeleev Commun., 1998, no. 5, pp. 187–188.

  16. Meunier, B.,Chem. Rev., 1992, vol. 92, p. 1411.

    Article  CAS  Google Scholar 

  17. Perie, K., Barbe, J.-V., Cocolios, P., and Guilard, R.,Bull. Soc. Chim. Fr., 1996, vol. 133, p. 697.

    CAS  Google Scholar 

  18. Bhirappa, P. and Krishnan, V.,Inorg. Chem., 1991, vol. 30, p. 239.

    Article  Google Scholar 

  19. Bartoli, J., Brigaud, O., Battioni, P., and Monsuy, D.,J. Chem. Soc. Chem. Commun., 1991, no. 2, p. 440.

  20. Buchler, J.W., Lay, K.-L., and Stoppa, H.,Z. Naturforschung Anorg. Chem. Org. Chem., 1980, vol. 35B, pp. 435–438.

    Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to A. F. Mironov.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Rumyantseva, V.D., Aksenova, E.A., Ponamoreva, O.N. et al. Halogenation of metalloporphyrins. Russ J Bioorg Chem 26, 423–428 (2000).

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI:

Key words

  • chlorination
  • metalloporphyrins
  • thionyl chloride
  • transient metals