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

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. 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. 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. 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

    CAS  Article  Google Scholar 

  4. 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

    CAS  Article  Google Scholar 

  5. 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

    CAS  Article  Google Scholar 

  6. 6

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

    CAS  Article  Google Scholar 

  7. 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

    CAS  Article  Google Scholar 

  8. 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

    CAS  Article  Google Scholar 

  9. 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

    CAS  Article  Google Scholar 

  10. 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

    CAS  Article  Google Scholar 

  11. 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

    CAS  Article  Google Scholar 

  12. 12

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

  13. 13

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

  14. 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. 15

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

    CAS  Article  Google Scholar 

  16. 16

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

  17. 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

    CAS  Article  Google Scholar 

  18. 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

    CAS  Article  Google Scholar 

  19. 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

    CAS  Article  Google Scholar 

  20. 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

    CAS  Article  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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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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Keywords:

  • octaethylporphyrin
  • meso-nitro-substituted porphyrins
  • cobalt complexes
  • nitration reactions
  • complexation