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Synthesis and Spectral Properties of meso-Nitro-Substituted Octaethylporphyrins and Their Co(II) Complexes

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Abstract

The reaction of 2,3,7,8,12,13,17,18-octaethylporphyrin with sodium nitrite in trifluoroacetic acid produced 5-nitro-2,3,7,8,12,13,17,18-octaethylporphyrin, 5,15-dinitro-2,3,7,8,12,13,17,18-octaethylporphyrin, and 5,10,15-trinitro-2,3,7,8,12,13,17,18-octaethylporphyrin. Reactions of octaethylporphyrin, mono-, di-, tri-, and tetranitro-substituted porphyrins coordination to cobalt(II) acetate in a chloroform–methanol mixture were studied. The corresponding Co(II) porphyrinates were obtained and identified. It was shown that, upon dissolution of Co(II) octaethylporphyrinates in dimethylformamide in the presence of NaOH, the Co(II)→Co(III) oxidation occurs in the coordination site of the macrocycle.

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REFERENCES

  1. Lu-Lin, Li. and Wei-Guang Diau, E., Chem. Soc. Rev., 2013, vol. 42, no. 1, p. 291. https://doi.org/10.1039/C2CS35257E

    Article  Google Scholar 

  2. Zdanovich, S.A., Mamardashvili, N.Z., and Golubchikov, O.A., Russ. J. Org. Chem., 1996, vol. 32, no. 5, p. 756.

    Google Scholar 

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

    Article  CAS  Google Scholar 

  4. Lyubimtsev, A., Semeikin, A., Zhglova, N., Sheinin, V., Rulikova, O., and Syrbu, S., Makrogeterotsikly, 2018, vol. 11, no. 1, p. 103. https://doi.org/10.6060/mhc171151l

    Article  CAS  Google Scholar 

  5. Luguya, R., Jaquinod, L., Fronczek, F.R., Graca, M., Vicente, 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 

  6. Gong, L.Ch. and Dolphin, D., Can. J. Chem., 1985, vol. 63, no. 2, p. 401. https://doi.org/10.1139/v85-066

    Article  CAS  Google Scholar 

  7. Watanabe, E., Nichimura, S., Ogoshi, H., and Yoshida, Z., Tetrahedron, 1975, vol. 31, nos. 11–12, p. 1385. https://doi.org/10.1016/0040-4020(75)87068-2

    Article  CAS  Google Scholar 

  8. Chizhova, N.V., Kumeev, R.S., and Mamardashvili, N.Z., Russ. J. Inorg. Chem., 2013, vol. 58, no. 6, p. 740. https://doi.org/10.1134/S0036023613060089

    Article  CAS  Google Scholar 

  9. Chizhova, N.V., Zvezdina, S.V., and Mamardashvili, N.Z., Russ. J. Gen. Chem., 2016, vol. 86, no. 5, p. 1091. https://doi.org/10.1134/S1070363216050182

    Article  CAS  Google Scholar 

  10. Mamardashvili, G.M., Simonova, O.R., Chizhova, N.V., and Mamardashvili, N.Z., Russ. J. Gen. Chem., 2018, vol. 88, no. 6, p. 1154. https://doi.org/10.1134/S107036321806018X

    Article  CAS  Google Scholar 

  11. Chizhova, N.V., Khelevina, O.G., Kumeev, R.S., Berezin, B.D., and Mamardashvili, N.Z., Russ. J. Gen. Chem., 2010, vol. 80, no. 11, p. 2387. https://doi.org/10.1134/S1070363210110253

    Article  CAS  Google Scholar 

  12. Porfiriny: Spektroskopiya, electrokhimiya, primenenie (Porphyrins: Spectroscopy, Electrochemistry, Application), Enikolopyan, N.S., Ed., Moscow: Nauka, 1987.

  13. Mann, Ch.K. and Barnes, K.K., Electrochemical Reactions in Nonaqueous Systems, New York: Marcel Dekker, 1970.

  14. 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

  15. Cao, Y., Peterson, J.L., and Stolzenberg, A.M., Inorg. Chem., 1998, vol. 37, p. 5173. https://doi.org/10.1021/ic980538u

    Article  CAS  Google Scholar 

  16. Koordinatsionnye soedineniya porfirinov i ftalotsianina (Coordination Compounds of Porphyrins and Phthalocyanine), Moscow: Nauka, 1978.

  17. Sheinin, V.B., Chizhova, N.V., and Romanova, A.O., Russ. J. Gen. Chem., 2010, vol. 80, no. 2, p. 351. https://doi.org/10.1134/S107036321002026X

    Article  CAS  Google Scholar 

  18. Chizhova, N.V., Maltceva, O.V., Zvezdina, S.V., Mamardashvili, N.Z., and Koifman, O.I., J. Coord. Chem., 2018, vol. 71, no. 19, p. 3222. https://doi.org/10.1080/00958972.2018.1519186

    Article  CAS  Google Scholar 

  19. Mamardashvili, G.M., Chizhova, N.V., Kaigorodova, E.Y., and Mamardashvili, N.Zh., Russ. J. Inorg. Chem., 2017, vol. 62, no. 3, p. 301. https://doi.org/10.1134/S0036023617030123

    Article  CAS  Google Scholar 

  20. Chizhova, N.V., Mal’tseva, O.V., Zav’yalov, A.V., and Mamardashvili, N.Z., Russ. J. Inorg. Chem., 2017, vol. 62, no. 5, p. 683. https://doi.org/10.1134/S0036023617050072

    Article  CAS  Google Scholar 

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Funding

The work was supported by the Russian science Foundation (project no. 19-73-20079) using the equipment of the collective use center of the Zelinsky Institute of organic chemistry of the Russian Academy of Sciences.

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  1. G.A. Krestov Institute of Chemistry of Solutions of the Russian Academy of Sciences, 153040, Ivanovo, Russia

    N. V. Chizhova, A. I. Rusanov & N. Zh. Mamardashvili

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  1. N. V. Chizhova
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  2. A. I. Rusanov
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  3. N. Zh. Mamardashvili
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Correspondence to N. V. Chizhova.

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Chizhova, N.V., Rusanov, A.I. & Mamardashvili, N.Z. Synthesis and Spectral Properties of meso-Nitro-Substituted Octaethylporphyrins and Their Co(II) Complexes. Russ J Gen Chem 90, 1878–1883 (2020). https://doi.org/10.1134/S1070363220100102

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