Skip to main content
Log in

Synthesis and Spectral Properties of Unsymmetrically Substituted Mn(II) and Mn(III) Octaethylporphyrins

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

5-Mononitro-2,3,7,8,12,13,17,18-octaethylporphyrin, 5,10,15-trinitro-2,3,7,8,12,13,17,18-octaethylporphyrin, and their Cd(II) complexes were synthesized. The coordination reactions of 2,3,7,8,12,13,17,18-octaethylporphyrin and its mono- and trinitro-substituted derivatives and the metal-exchange reactions of the synthesized Cd(II) octaethylporphyrin complexes with Mn(II) chloride in DMF were investigated by spectrophotometry. The corresponding Mn(II) and Mn(III) porphyrins were obtained and identified. The kinetic parameters of the studied reactions were determined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme
Scheme
Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

REFERENCES

  1. Li, L.-L. and Diau, E.W.-G., Chem. Soc. Rev., 2013, vol. 42, p. 291. https://doi.org/10.1039/C2CS35257E

    Article  CAS  PubMed  Google Scholar 

  2. Stuzhin, P.A., Goryachev, M.Yu., Ivanova, S.S, Nazarova, A., Pimkov, I., and Koifman, O.I., J. Porphyr. Phthalocyanines, 2013, vol. 17, p. 905. https://doi.org/10.1142/S1088424613500892

    Article  CAS  Google Scholar 

  3. Luguya, R., Jaquinod, L., Fronczek, F.R., Vicente, M.G.H., and Smith, K.M., Tetrahedron, 2004, vol. 60, p. 2757. https://doi.org/10.1016/j.tet.2004.01.080

    Article  CAS  Google Scholar 

  4. Lyubimtsev, A., Semeikin, A., Zheglova, N., Sheinin, V., Kulikova, O., and Syrbu, S., Macroheterocycles, 2018, vol. 11, p. 103. https://doi.org/10.6060/mhc171151

    Article  CAS  Google Scholar 

  5. Gong, L.Ch. and Dolphin, D., Can. J. Chem., 1985, vol. 63, p. 401. https://doi.org/10.1139/v85-066

    Article  CAS  Google Scholar 

  6. Watanabe, E., Nichimura, S., Ogoshi, H., and Yoshida, Z., Tetrahedron, 1975, vol. 31, p. 1385. https://doi.org/10.1016/0040-4020(75)87068-2

    Article  CAS  Google Scholar 

  7. Yatsimirskii, K.B., Vvedenie v bioneorganicheskuyu khimiyu (Introduction to Bioinorganic Chemistry), Kiev: Naukova Dumka, 1976.

  8. da Silva, V.S., Teixeira, L.I., do Nascimentoa, E., Idemoria, Y.M., and De Freitas-Silva, G., Appl. Catal. A: Gen., 2014, vol. 469, p. 124. https://doi.org/10.1016/j.apcata.2013.09.033

    Article  CAS  Google Scholar 

  9. Chizhova, N.V., Zvezdina, S.V., and Kataleva, Y.S., Russ. J. Gen. Chem., 2015, vol. 85, p. 1132. https://doi.org/10.1134/S1070363215050217

    Article  CAS  Google Scholar 

  10. Chizhova, N.V., Maltceva, O.V., Zvezdina, S.V., Mamardashvili, N.Z., and Koifman, O.I., J. Coord. Chem., 2018, vol. 71, p. 3222. https://doi.org/10.1080/00958972.2018.1519186

    Article  CAS  Google Scholar 

  11. Cheng, B., Cukiernik, F., Fries, P.H., Marchon, J.C., and Scheidt, W.R., Inorg. Chem., 1995, vol. 34, p. 4627. https://doi.org/10.1021/ic00122a020

    Article  CAS  Google Scholar 

  12. Berezin, B.D., Koordinatsionnye soedineniya porfirinov i ftalotsianina (Coordination Compounds of Porphyrins and Phthalocyanine), Moscow: Nauka, 1978.

  13. Mamardashvili, G.M., Mamardashvili, N.Zh., and Koifman, O.I.,Russ. Chem. Rev., 2008, vol. 77, p. 59. https://doi.org/10.1070/RC2008v077n01ABEH003743

    Article  CAS  Google Scholar 

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

  15. Berezin, B.D., Rumyantseva, S.V., and Berezin, M.B., Russ. J. Coord. Chem., 2004, vol. 30, p. 291. https://doi.org/10.1023/B:RUCO.0000022806.85114.93

    Article  CAS  Google Scholar 

  16. Boucher, L.J., Coord. Chem. Rev., 1972, vol. 7, p. 289. https://doi.org/10.1016/S0010-8545(00)80024-7

    Article  CAS  Google Scholar 

  17. Doro, F.G., Lindsay Smith, J.R., Ferreira, A.G., and Assis, M.D.,J. Mol. Catal. Chem., 2000, vol. 164, p. 97. https://doi.org/10.1016/S1381-1169(00)00352-6

    Article  CAS  Google Scholar 

  18. Berezin, B.D., Karmanova, T.V., Gromova, T.V., Syrbu, S.A., and Semeikin, A.S., Russ. J. Coord. Chem., 2002, vol. 28, p. 608. https://doi.org/10.1023/A:1020030714257

    Article  CAS  Google Scholar 

  19. Hambright, R., The Porphyrin Handbook, Chemistry of Water Soluble Porphyrins. Kadish, K.M., Smith, K.M., and Guilard, R., Eds., New York: Academic Press, 2000, vol. 3, p. 129.

  20. Yatismirskii, K.B. and Lampeka, Ya.D., Fizikokhimiya kompleksov metallov s makrotsilicheskimi ligandami (Physicochemistry of Metal Complexes with Macrocyclic Ligands), Kiev: Naukova Dumka, 1985.

  21. Basolo, F. and Pearson, R.G., Mechanisms of Inorganic Reactions a Study of Metal Complexes in Solution, New York: John Wiley and Sons, Inc., 1967.

  22. Gubin, S.P., Khimiya klasterov. Osnovy klassifikatsii i stroeniya (Cluster chemistry. Basics of Classification and Structure), Moscow: Nauka, 1987.

  23. Entelis, S.G., Kinetika reaktsii v zhidkoi faze (Kinetics of Reactions in the Liquid Phase), Entelis, S.G. and Tiger, R.P., Eds., Moscow: Khimiya, 1973, p. 416.

  24. Chizhova, N.V., Khelevina, J.G., and Berezin, B.D., Russ. J. Gen. Chem., 2003, vol. 73, p. 1645. https://doi.org/10.1023/B:RUGC.0000016039.52090.d2

    Article  CAS  Google Scholar 

  25. Linstead, R.P. and Weiss, F.T., J. Chem. Soc., 1950, p. 2975. https://doi.org/10.1039/JR9500002975

  26. Cook, A.H. and Linstead, R.P., J. Chem. Soc., 1937, p. 929. https://doi.org/10.1039/JR9370000929

  27. Ali, B.B., Belkhiria, M.S., Giorgi, M., and Nasri, H., Open J. Inorg. Chem., 2011, p. 39. https://doi.org/10.4236/ojic.2011.13006

  28. Zvezdina, S.V., Berezin, M.B., and Berezin, B.D., Russ. J. Inorg. Chem., 2007, vol. 52, p. 1269. https://doi.org/10.1134/S0036023607080177

    Article  Google Scholar 

  29. Zvezdina, S.V. and Mamardashvili, N.Zh., Russ. J. Coord. Chem., 2012, vol. 38, p. 323. https://doi.org/10.1134/S1070328412050120

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The work was performed using the equipment of the “Upper Vologa Regional Center for Physical and Chemical Research” Center for Collective Use.

Funding

The work was financially supported by the Russian Foundation for Basic Research: project no. 19-03-00078_A [synthesis of porphyrin ligands and their Cd(II), Mn(II), and Mn(III) complexes] and project no. 1843370001_r-a [study of the metal-exchange reaction of the Cd(II) complexes of the synthesized porphyrins with Mn(II) chloride].

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. V. Zvezdina.

Ethics declarations

The authors declare no conflict of interest.

Supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zvezdina, S.V., Chizhova, N.V. & Mamardashvili, N.Z. Synthesis and Spectral Properties of Unsymmetrically Substituted Mn(II) and Mn(III) Octaethylporphyrins. Russ J Org Chem 56, 1374–1382 (2020). https://doi.org/10.1134/S1070428020080072

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020080072

Keywords:

Navigation