Abstract
The electrochemical behavior of tetra-4-[4-(2,4,5-trichlorophenoxy)]phthalocyaninates of cobalt(II) (CoPc) and copper(II) (CuPc) in N,N-dimethylformamide with 0.1 M nBu4NBF4 as a supporting electrolyte is studied by cyclic voltammetry. It is shown experimentally that both metal complexes are capable of irreversible reduction. In this case, the reverse CV-scan for CoPc demonstrates an oxidation peak which is absent in the anodic scan and corresponds to the cathodic reaction product. The metal complexes themselves are not oxidized under these conditions.
Similar content being viewed by others
REFERENCES
De la Torre, G., Claessens, C.G., and Torres, T., Phthalocyanines: old dyes, new materials. Putting color in nanotechnology, Chem. Commun., 2007, vol. 20, p. 2000. https://doi.org/10.1039/B614234F
Wöhrle, D., Schnurpfeil, G., Makarov, S.G., Kazarin, A., and Suvorova, O.N., Practical applications of phthalocyanines – from dyes and pigments to materials for optical, electronic and photo-electronic devices, Macroheterocycles, 2012, vol. 5, no. 3, p. 191. https://doi.org/10.6060/mhc2012.120990w
Koifman, O.I., Ageeva, T.A., Beletskaya, I.P., Averin, A.D., Yakushev, A.A., Tomilova, L.G., Dubinina, T.V., Tsivadze, A.Yu., Gorbunova, Yu.G., Martynov, A.G., Konarev, D.V., Khasanov, S.S., Lyubovskaya, R.N., Lomova, T.N., Korolev, V.V., et al., Macroheterocyclic compounds a key building block in new functional materials and molecular devices, Macroheterocycles, 2020, vol. 13, no. 4, p. 311. https://doi.org/10.6060/mhc200814k
Kondratenko, N.V., Nemykin, V.N., Lukyanets, E.A., Kostromina, N.A., Volkovan, S.V., and Yagupolskii, L.M., The synthesis and properties of some polyfluoroalkoxy substituted phthalocyanines, J. Porphyrins Phthalocyanines, 1997, vol. 1, no. 4, p. 341. https://doi.org/10.1002/(SICI)1099-1409(199710)1:4<341::AID-JPP37>3.0.CO;2-K
Furuyama, T., Satoh, K., Kushiya, T., and Kobayashi, N., Design, synthesis, and properties of phthalocyanine complexes with main-group elements showing main absorption and fluorescence beyond 1000 nm, J. Amer. Chem. Soc., 2014, vol. 136, no. 2, p. 765. https://doi.org/10.1021/ja411016f
Sorokin, A.B., Phthalocyanine metal complexes in catalysis, Chem. Rev., 2013, vol. 113, no. 10, p. 8152. https://doi.org/10.1021/cr4000072
Koifman, O.I. and Ageeva, T.A., Common approaches to the synthesis of tetrapyrrole macroheterocyclic compounds: promising materials for photovoltaic devices, Polym. Sci., Ser. C, 2014, vol. 56, no. 1, p. 84. https://doi.org/10.1134/S1811238214010056
Vashurin, A.S., Badaukaite, R.A., Futerman, N.A., Pukhovskaya, S.G., Shaposhnikov, G.P., and Golubchikov, O.A., Catalytic properties of polymer matrix-immobilized cobalt complexes with sulfonated phthalocyanines, Pet. Chem., 2013, vol. 53, no. 3, p. 197. https://doi.org/10.1134/S0965544113030122
Botnar, A., Tikhomirova, T., Kazaryan, K., Bychkova, A., Maizlish, V., Abramov, I., and Vashurin, A., Synthesis and properties of tetrasubstituted phthalocyanines containing cyclohexylphenoxy-groups on the periphery, J. Mol. Struct., 2021, vol. 1238, p. 130438. https://doi.org/10.1016/j.molstruc.2021.130438
Erzunov, D., Tikhomirova, T., Filippov, D., Maizlish, V., Abramov, I., and Vashurin, A., Tetrasubstituted (4‑chlorophenoxy)- and (2,4,5-trichlorophenoxy)phthalocyanine metal(II) complexes and their sulphonated derivatives: synthesis and properties, Eur. Chem. Bull., 2019, vol. 8, no. 11, p. 376. https://doi.org/10.17628/ecb.2019.8.376-382
Vashurin, A.S., Kuzmin, I.A., Litova, N.A., Petrov, O.A., Pukhovskaya, S.G., and Golubchikov, O.A., Catalytic properties of cobalt complexes with tetrapyrazino porphyrazine and phthalocyanine derivatives, Russ. J. Phys. Chem. A, 2014, vol. 88, no. 12, p. 2064. https://doi.org/10.1134/S0036024414120395
Vashurin, A., Maizlish, V., Pukhovskaya, S., Voronina, A., Kuzmin, I., Futerman, N., Golubchikov, O., and Koifman, O., Novel aqueous soluble cobalt(II) phthalocyanines of tetracarboxyl-substituted: Synthesis and catalytic activity on oxidation of sodium diethyldithiocarbamate, J. Porphyrins Phthalocyanines, 2015, vol. 19, no. 4, p. 573. https://doi.org/10.1142/S1088424614501028
Petrov, A.V., Bazanov, M.I., and Yurina, E.S., Electrochemical and electrocatalytic properties of metal-polymer and macroheterocyclic complexes with cobalt, Elektrohim. Energ., 2010, vol. 10, no. 3, p. 141.
Turchaninova, I.V., Filimonov, D.A., Bazanov, M.I., and Maizlish, V.E., Study of electrochemical and electrocatalytic properties of certain copper phthalocyanine derivatives, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 2011, vol. 54, no. 2, p. 105.
Gogin, K.K., Znoiko, S.A., Nakonechnaya, A.N., Kustova, T.V., Akopova, O.B., Bumbina, N.V., and Usol’tseva, N.V., Synthesis and properties of tetra[4,5](2,4,5-trichlorophenoxy)phthalocyanine metal complexes, Zhidk. Krist. Ikh Prakt. Ispol’z., 2020, vol. 20, no. 4, p. 35. https://doi.org/10.18083/LCAppl.2020.4.35
Alpatova, N.M., Ovsyannikova, E.V., Semenikhin, O.A., Tomilova, L.G., Korenchenko, O.V., and Kazarinov, V.E., Effect of solvent and supporting electrolyte on redox conversions of electropolymerized copper tetraaminophthalocyanine, Russ. J. Electrochem., 2000, vol. 36, p. 155.] https://doi.org/10.1007/BF02756899
Nevin, W.A., Hempstead, M.R., Liu, W., Leznoff, C.C., and Lever, A.B.P., Electrochemistry and spectroelectrochemistry of mononuclear and binuclear cobalt phthalocyanines, Inorg. Chem., 1987, vol. 26, no. 4, p. 570. https://doi.org/10.1021/ic00251a017
Bazanov, M.I., Filimonov, D.A., Volkov, A.V., and Koifman, O.I., Makrotsiklicheskie soedineniya: elektrokhimiya, elektrokataliz, termokhimiya (Macroheterocyclic Compounds: Electrochemistry, Electrocatalysis, Thermochemistry), Moscow: LENAND, 1974.
ACKNOWLEDGMENTS
The study was carried out using the resoursces of the Center for Shared Use of Scientific Equipment of the Ivanovo State University of Chemistry and Technology (with the support of the Ministry of Science and Higher Education of the Russian Federation, grant no. 075-15-2021-671). The studies by I.F. Sakhapov, Z.N. Gafurov, and D.G. Yakhvarov were supported by the State Project of the Federal Research Center of the Kazan Scientific Center of the Russian Academy of Sciences.
Funding
This study was financially supported by the Council for Grants of the President of the Russian Federation (project no. MK-4839.2022.1.3).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interest.
Additional information
Translated by T. Safonova
Rights and permissions
About this article
Cite this article
Kovanova, M.A., Tikhomirova, T.V., Sakhapov, I.F. et al. Peculiarities of the Electrochemical Behavior of Chlorophenoxy-Substituted Phthalocyanines of Cobalt and Copper in Non-Aqueous Media. Russ J Electrochem 59, 646–650 (2023). https://doi.org/10.1134/S1023193523090070
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1023193523090070