Synthesis and properties of asymmetricly substituted Mn(III)-nitro-phenylporphirins

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Abstract

Mn(III)-5-(4-nitrophenyl)-10,15,20-triphenylporphyrin and Mn(III)-5,10,15-tri-(4-nitrophenyl)-20-phenylporphyrin were synthesized using the reactions of complex formation of corresponding porphyrins and metal exchange of their Cd complexes with MnCl2 in dimethylformamide. Partial reduction of Mn(III) to Mn(II) is observed upon dissolution of manganese(III) complexes in dimethylformamide. When NaOH solid is added to a solution of dimethylformamide and in ethanolamine unstable Mn(II) porphyrins are formed. The photochemical stability and oxidative degradation of Mn(III)-porphyrins have been studied. The metal exchange reaction of asymmetricaly substituted Cd(II)-porphyrins with manganese chloride in dimethylformamide has been studied. The kinetic parameters of the reaction were calculated. The influence of substituends and the nature of the salt on the kinetic parameters of the metal exchange reaction was revealed. The synthesized compounds were identified by methods UV-Vis, IR, 1H NMR spectroscopy and mass spectrometry.

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About the authors

N. V. Chizhova

Krestov Institute of Solutions Chemistry Russian Academy of Sciences

Email: ngm@isc-ras.ru
Russian Federation, Ivanovo, 153040

S. V. Zvezdina

Krestov Institute of Solutions Chemistry Russian Academy of Sciences

Email: ngm@isc-ras.ru
Russian Federation, Ivanovo, 153040

A. E. Likhonina

Krestov Institute of Solutions Chemistry Russian Academy of Sciences

Email: ngm@isc-ras.ru
Russian Federation, Ivanovo, 153040

N. Zh. Mamardashvili

Krestov Institute of Solutions Chemistry Russian Academy of Sciences

Author for correspondence.
Email: ngm@isc-ras.ru
Russian Federation, Ivanovo, 153040

O. I. Koifman

Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Email: ngm@isc-ras.ru
Russian Federation, Moscow, 119991

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Supplementary files

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2. Fig. 1. ESP of the complex: a - manganese(III) 5 in chloroform (C = 3 × 10–5 mol/l), 25C; b - mixtures of Mn(II) and Mn(III) complexes with 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin in DMF during dissolution (C ~ 5.5–6.0 × 10–5 mol/l), 25 C; c — Mn(II) complex 8 in ethanolamine (C = 4.1 × 10–5 mol/l), 25C.

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3. Fig. 2. ESP of a mixture of Mn(II) and Mn(III) complexes with 5,10,15-tri-(4-nitrophenyl)-20-phenylporphyrin in DMF (a): 1 — upon dissolution (C = 3.6 × 10–5 mol/l), 2 — after 20 minutes, 3 — after 1 hour, 25C. Change in the ESP of the Mn(III) 6 complex in DMF + NaOHsol: 1 — after 5 min (C ~ 3.4 × 10–5 mol/l), 2 — 15 min, 3 — 30 min, 25C.

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4. Fig. 3. Mass spectrum of manganese-5,10,15-tri-(4-nitrophenyl)-20-phenylporphyrin.

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5. Fig. 4. IR spectra of complexes 6, 7 in KBr tablets.

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6. Fig. 5. Change in the ESP of compound 7 in chloroform–H2O2 (С = 0.22 mol/l), 25C.

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7. Fig. 6. Dependence of log(C0CdP/CCdP) on the time of the metal exchange reaction of compound 3 with MnCl2 in DMF: CMnCl2 = 2.0 × 10–3 mol/l, T = 288 (1), 298 (2), 308 K (3).

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8. Fig. 7. Dependence of log keff on log CMnCl2 metal exchange of complex 3 with MnCl2 in DMF at T = 288 (1), 298 (2), 308 K (3).

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9. Scheme

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