Skip to main content
SpringerLink
Log in

Electrochemical route to Co(II) polyporphine

  • Original Paper
  • Published:
Journal of Solid State Electrochemistry Aims and scope Submit manuscript

Abstract

Novel synthetic route towards electroactive films of Co(II) polyporphine has been elaborated. It is based on the electrochemical transformation of the metal-free polyporphine film with replacement of protons inside the macrocycles by Co(II) cations. Compared to the conventional procedure of such ion exchange based on extended thermal treatment of macrocycles in the presence of the saturated solution of the metal salt, the developed approach allows one to use dilute solutions of the metal cation at ambient conditions. The resulting Co(II) polyporphine possesses a very high concentration of CoN4 functional groups which are known as prospective catalysts of various processes.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Suslick KS, Rakow NA, Kosal ME, Chou JH (2000) The materials chemistry of porphyrins and metalloporphyrins. J Porphyr Phthalocyanines 4:407–413

    Article  CAS  Google Scholar 

  2. Lin S, Diercks CS, Zhang YB, Kornienko N, Nichols EM, Zhao Y, Paris AR, Kim D, Yang P, Yaghi OM, Chang CJ (2015) Covalent organic frameworks comprising cobalt porphyrins for catalytic CO2 reduction in water. Science 349:1208–1213

    Article  CAS  Google Scholar 

  3. Rocklin RD, Murray RW (1979) Chemically modified carbon electrodes: part XVII. Metallation of immobilized tetra (aminophenyl) porphyrin with manganese, iron, cobalt, nickel, copper and zinc, and electrochemistry of diprotonated tetraphenylporphyrin. J. Electroanal. Chem. Interfacial Electrochem. 100:271–282

    Article  CAS  Google Scholar 

  4. Jester CP, Rocklin RD, Murray RW (1980) Electron transfer and axial coordination reactions of cobalt tetra (aminophenyl) porphyrins covalently bonded to carbon electrodes. J Electrochem Soc 127:1979–1985

    Article  CAS  Google Scholar 

  5. Tarasevich MR, Bogdanovskaya VA (1987) The surface-modified carbon materials for electrocatalysis. Russ Chem Rev 56:653–669

    Article  Google Scholar 

  6. Bettelheim A, White BA, Raybuck SA, Murray RW (1987) Electrochemical polymerization of amino-, pyrrole-, and hydroxy-substituted tetraphenylporphyrins. Inorg Chem 26:1009–1017

    Article  CAS  Google Scholar 

  7. Armengaud C, Moisy P, Bedioui F, Devynck J, Bied-Charreton C (1990) Electrochemistry of conducting polypyrrole films containing cobalt porphyrin. J Electroanal Chem Interfacial Electrochem 277:197–211

    Article  CAS  Google Scholar 

  8. Walter M.G., Wamser C.C. (2007) Synthesis and characterization of electropolymerized porphyrin nanofibers, MRS Proceedings. Cambridge University Press 1013 Z04-07

  9. Dogutan DK, Ptaszek M, Lindsey JS (2007) Direct synthesis of magnesium porphine via 1-formyldipyrromethane. J Org Chem 72:5008–5011

    Article  CAS  Google Scholar 

  10. Vorotyntsev MA, Konev DV, Devillers CH, Bezverkhyy I, Heintz O (2010) Magnesium(II) polyporphine: the first electron-conducting polymer with directly linked unsubstituted porphyrin units obtained by electrooxidation at a very low potential. Electrochim Acta 55:6703–6714

    Article  CAS  Google Scholar 

  11. Konev DV, Istakova OI, Sereda OA, Shamraeva MA, Devillers CH, Vorotyntsev MA (2015) In situ UV-visible spectroelectrochemistry in the course of oxidative monomer electrolysis. Electrochim Acta 179:315–325

    Article  CAS  Google Scholar 

  12. Vorotyntsev MA, Konev DV, Devillers CH, Bezverkhyy I, Heintz O (2011) Electroactive polymeric material with condensed structure on the basis of magnesium (II) polyporphine. Electrochim Acta 56:3436–3442

    Article  CAS  Google Scholar 

  13. Konev DV, Vorotyntsev MA, Devillers CH, Zyubina TS, Zyubin AS, Lizgina KV, Volkov AG (2013) Synthesis of new polyporphines by replacing central ion in magnesium polyporphine. Russ J Electrochem 49:753–758

    Article  CAS  Google Scholar 

  14. Konev DV, Devillers CH, Lizgina KV, Zyubina TS, Zyubin AS, Valkova LA, Vorotyntsev MA (2014) Synthesis of new electroactive polymers by ion-exchange replacement of Mg(II) by 2H+ or Zn(II) cations inside Mg(II) polyporphine film, with their subsequent electrochemical transformation to condensed-structure materials. Electrochim Acta 122:3–10

    Article  CAS  Google Scholar 

  15. Rolle SD, Konev DV, Devillers CH, Lizgina KV, Lucas D, Stern C, Herbst F, Vorotyntsev MA (2016) Efficient synthesis of a new electroactive polymer of Co (II) porphine by in-situ replacement of Mg (II) inside Mg (II) polyporphine film. Electrochim Acta 204:276–286

    Article  CAS  Google Scholar 

  16. Ji Y, Li Z, Wang S, Xu G, Yu X (2010) Thermal treatment of Co (II) tetracarboxyphenyl porphyrin supported on carbon as an electrocatalyst for oxygen reduction. Int J Hydrog Energy 35:8117–8121

    Article  CAS  Google Scholar 

  17. Bennett JE, Malinski T (1991) Conductive polymeric porphyrin films: application in the electrocatalytic oxidation of hydrazine. Chem Mater 3:490–495

    Article  CAS  Google Scholar 

  18. Di Natale C, Paolesse R, Burgio M, Martinelli E, Pennazza G, D’Amico A (2004) Application of metalloporphyrins-based gas and liquid sensor arrays to the analysis of red wine. Anal Chim Acta 513:49–56

    Article  CAS  Google Scholar 

  19. Paolesse R, Di Natale C, Burgio M, Martinelli E, Mazzone E, Palleschi G, D’Amico A (2003) Porphyrin-based array of cross-selective electrodes for analysis of liquid samples. Sens Actuators B-Chem 95:400–405

    Article  CAS  Google Scholar 

  20. Dostal A, Hermes M, Scholz F (1996) The formation of bilayered nickel-iron, cadmium-iron and cadmium-silver hexacyanoferrates by an electrochemically driven insertion-substitution mechanism. J Electroanal Chem 415:133–141

    Article  CAS  Google Scholar 

  21. Hermes M, Lovric M, Hartl M, Retter U, Scholz F (2001) On the electrochemically driven formation of bilayered systems of solid Prussian-blue-type metal hexacyanoferrates: a model for Prussian blue _ cadmium hexacyanoferrate supported by finite difference simulations. J Electroanal Chem 501:193–204

    Article  CAS  Google Scholar 

  22. Todd WJ, Bailly F, Pavez J, Faguy PW, Baldwin RP, Buchanan RM (1998) Electrochemically induced metallation of polymeric phthalocyanines. J Am Chem Soc 120:4887–4888

    Article  CAS  Google Scholar 

  23. Konev DV, Devillers CH, Lizgina KV, Baulin VE, Vorotyntsev MA (2015) Electropolymerization of non-substituted Mg (II) porphine: effects of proton acceptor addition. J Electroanal Chem 737:235–242

    Article  CAS  Google Scholar 

  24. Kadish K. M., Caemelbecke E. V., Royal G. (2000) Electrochemistry of metalloporphyrins in Nonaqueous Media. In: The Porphyrin Handbook / Eds Kadish K. M., Smith K. M. Guilard R. Academic Press, V. 8. Chapter 55. P. 1–114

  25. Kalaji M, Peter LM, Abrantes LM, Mesquita JC (1989) Microelectrode studies of fast switching in polyaniline films. J Electroanal Chem 274:289–295

    Article  CAS  Google Scholar 

  26. Aoki K, Cao J, Hoshino Y (1993) Coulombic irreversibility at polyaniline-coated electrodes by electrochemical switching. Electrochim Acta 38:1711–1716

    Article  CAS  Google Scholar 

  27. Vorotyntsev MA, Skompska M, Pousson E, Goux J, Moise C (2003) Memory effects in functionalized conducting polymer films: titanocene derivatized polypyrrole in contact with THF solutions. J Electroanal Chem 552:307–317

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The study has been carried out with the financial support of the Russian Science Foundation (project: 14-13-01244). CHD thanks the CNRS for granting him the opportunity to work as a full-time researcher for 1 year (“delegation CNRS,” September 2015).

Author information

Authors and Affiliations

  1. D. I. Mendeleev Russian University of Chemical Technology of Russia, Moscow, Russia

    O. I. Istakova, D. V. Konev & M. A. Vorotyntsev

  2. Institute for Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Russia

    O. I. Istakova, D. V. Konev, A. S. Zyubin & M. A. Vorotyntsev

  3. ICMUB, UMR 6302 CNRS-Université de Bourgogne-Franche-Comté, Dijon, France

    C. H. Devillers & M. A. Vorotyntsev

  4. M. V. Lomonosov Moscow State University, Moscow, Russia

    M. A. Vorotyntsev

Authors
  1. O. I. Istakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Konev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. S. Zyubin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. C. H. Devillers
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. A. Vorotyntsev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to D. V. Konev, C. H. Devillers or M. A. Vorotyntsev.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Istakova, O.I., Konev, D.V., Zyubin, A.S. et al. Electrochemical route to Co(II) polyporphine. J Solid State Electrochem 20, 3189–3197 (2016). https://doi.org/10.1007/s10008-016-3397-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10008-016-3397-y

Keywords

Search

Navigation