Skip to main content

Oxidative degradation of porphyrins and metalloporphyrins under polythermal conditions

Abstract

Influence of structure on the thermal properties of a large group of natural and synthetic porphyrins (H2P) and metalloporphyrins (MP) was analyzed on the ground of thermogravimetric studies. The initial stage of thermal degradation of “classical” porphyrin containing a flat or pseudo-planar macrocycle is a result of oxidative degradation of the macrocyclic structure with the formation of linear tetrapyrrols. The negative effect on the thermal stability of porphyrins exerts the violation of the planar structure of the macrocycle, and the presence of bulky alkyl and polar pseudoalkyl substituents. In many cases, the general trend in the decrease in the stability of metalloporphyrins (MP) in comparison with the corresponding H2P is a consequence of intramolecular metal ↔ ligand redox processes.

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

References

  1. Askarov, K.A., Berezin, B.D., Bystritskaya, E.V. Kuz’minskii, V.A., Solov’ev, K.N., Golubchikov, O.A., Koifman, O.I., and Ponomarev, G.V., Porfiriny: spektroskopiya, spektrokhimiya, primenenie (Porphyrins: Spectroscopy, Spectrochemistry, and Application), Moscow: Nauka, 1987.

    Google Scholar 

  2. Falk, J.E., Porphyrins and Metalloporphyrins, Amserdam: Elsevier Publishing Co., 1964.

    Google Scholar 

  3. V’yugin, A.I., Antina, E.V., Berezin, M.B., Lebedeva, N.Sh., and Barannikov, V.P., in Khimiya rastvorov i tekhnologiya zhidkofaznykh materialov. Dostizheniya i perspektivy (Chemistry of Solutions and Technology of Liquid-Phase Materials. Results and Perspectives), Ivanovo, 2006, p. 86.

  4. Khelevina, O.G., Antina, E.V., Rumyantseva, S.V., and Lebedeva, N.Sh., Zh. Obshch. Khim., 2001, vol. 71, no. 7, p. 1124.

    Google Scholar 

  5. Antina, E.V., Barannikov, V.N., Berezin, M.B., and V’yugin, A.I., Fizicheskaya khimiya rastvorov makrotsiklicheskikh soedinenii (Physical Chemistry of Solutions of Macrocyclic Compounds), in Problemy khimii rastvorov i tekhnologii zhidkofaznykh materialov (Problems of the Chemistry of Solutions and Technology of Liquid-Phase Materials), Ivanovo: Inst. of Solution Chemistry, Russian Academy of Sciences, 2001, p. 217.

    Google Scholar 

  6. Balantseva, E.V., Antina, E.V., Berezin, M.B., and V’yugin, A.I., Zh. Fiz. Khim., 2004, vol. 78, no. 10, p. 1811.

    Google Scholar 

  7. Balantseva, E.V., Guseva, G.B., Antina, E.V., and Berezin, M.B., Abstract of Papers, 9th Int. Conf. on the Chemistry of Porphyrins and Their Analogues, Suzdal’, 2003, p. 41.

  8. Mis’ko, E.N., Berezin, D.B., and Antina, E.V., Abstract of Papers, 9th Int. Conf. on the Chemistry of Porphyrins and Their Analogues, Suzdal’, 2003, p.58.

  9. Mis’ko, E.N., Berezin, D.B., Antina, E.V., and Berezin, M.B., Deposited VINITI, Moscow, 2003, no. 1003B2003.

  10. Berezina, N.M., Balantseva, E.V., Antina, E.V., Berezin, M.B., and Semeikin, A.S., Abstract of Papers, 24th Sci. Session of Russian Seminar on the Chemistry of Pophyrins and Their Analogues, Ivanovo, 2006, p. 16.

  11. Berezin, D.B., Mis’ko, E.N., Antina, E.V., and Berezin, M.B., Zh. Obshch. Khim., 2006, vol. 76, no. 3, p. 506.

    Google Scholar 

  12. Berezina N.M., Antina, E.V., Balantseva, E.V., Berezin, M.B., Semeikin, A.S., Bazanov, M.I., and V’yugin, A.I., Izv. Vuzov. Khimiya i Khim. Tekhnol., 2008, vol. 51, no. 3, p. 15.

    CAS  Google Scholar 

  13. Golubchikov, O.A. and Perlovich, G.L., Termodinamika sublimatsii porfirinov (Thermodynamics of Sublimation of Porphyrins), in Uspekhi khimii porfirinov (Progress in the Chemistry of Porphyrins), Golubchikov, O.A., Ed., St. Petersburg: Inst. of Chemistry, St. Peteresburg State Univ., 1997, vol. 1, p. 223.

    Google Scholar 

  14. Edwards, L. and Dolphin, D.H., J. Molec. Spectr., 1971, vol. 38, p. 16.

    Article  CAS  Google Scholar 

  15. Berezin, B.D. and Enikolopyan, N.S., Metalloporfiriny (Metalloporphyrins), Moscow: Nauka, 1988.

    Google Scholar 

  16. Rabek, J.F., Methods in Polymer Chemistry, Moscow: Mir, 1983, part 2.

    Google Scholar 

  17. Ellis, J., Jackson, A.H., Jain, A.C., and Kenner, G.W., J. Chem. Soc., 1964, no. 6, p. 1935.

  18. Balantseva, E.V., Candidate Sci. (Chem.) Dissertation, Ivanovo, 2005.

  19. Askarov, K.A., Berezin, B.D., Evstigneeva, R.P., Enikolopyan, N.S., Kirillova, G.V., Koifman, O.I., Mironov, A.F., Ponomarev, G.V., Semeikin, A.S., and Khelevina, O.G., Porfiriny: struktura, svoistva, sintez (Porphyrins: Structure, Properties, and Synthesis), Moscow: Nauka, 1985.

    Google Scholar 

  20. Fiziko-khimicheskie svoistva okislov (Physico-Chemical Properties of Oxides), Samsonov, G.V., Ed., Moscow: Metallurgiya, 1978.

    Google Scholar 

  21. Kreshkov, A.P. and Yaroslavtsev, A.A., Kurs analiticheskoi khimii. Kachestvennyi analiz (Course of Analytical Chemistry. Qualitative Analysis), Kreshkov, A.P., Ed., Moscow: Khimiya, 1975.

    Google Scholar 

  22. Hambright, P., Chemistry of Water Soluble Porphyrins, in The Porphyrin Hand Book, 2000, vol. 3,ch. 18, p. 132.

    Google Scholar 

  23. Biesaga, M., Talanta, 2000, vol. 51, no. 1, p. 209.

    Article  CAS  Google Scholar 

  24. Merchat, M., Bertolini, G., and Gioacomini, P., Photochem. and Photobiol., B: Biology, 1996, vol. 32, p. 153.

    Article  CAS  Google Scholar 

  25. Balantseva, E.V. and Antina, E.V., Abstract of Papers, 3rd Int. Conf. “Extraction of Organic Compounds”(EOS-2005), Voronezh, 2005, p. 234.

  26. Balantseva, E.V., Antina, E.V., and Berezin, M.B., Abstract of Papers, 4th School on the Chemistry of Porphyrins and Related Compounds, and Conf. “New Acievements in the Synthesis of Tetrapyrrols,” St. Petersburg: St. Petersburg State Univ., 2005, p. 24.

    Google Scholar 

  27. Ekimova, M.S., Balantseva, E.V., Kuznetsov, O.Yu., and Antina, E.V., Abstract of Papers, 4th Congress of Ovchinnikov Biotechnology Society of Russia, Pushchino, 2006, p. 73.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V. Antina.

Additional information

Original Russian Text © E.V. Antina, E.V. Balantseva, M.B. Berezin, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 6, pp. 1029–1037.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Antina, E.V., Balantseva, E.V. & Berezin, M.B. Oxidative degradation of porphyrins and metalloporphyrins under polythermal conditions. Russ J Gen Chem 81, 1222–1230 (2011). https://doi.org/10.1134/S1070363211060260

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363211060260

Keywords

  • Porphyrin
  • General Chemistry
  • Macrocycle
  • Oxidative Degradation
  • Porphin