5-(2-quinolyl)tetrabenzoporphyrin and Its complexes with zinc, cobalt, copper and manganese. Synthesis, spectral, electrochemical and electrocatalytic properties

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Abstract

By reacting phthalimide with quinaldine in the presence of zinc oxide, 3-(quinolin-2-ylmethylene)isoindolin-1-one was synthesized. Heating its mixture with excess phthalimide and zinc acetate leads to the formation of zinc 5-(2-quinolyl)tetrabenzoporphyrinate, which, when treated with acid, is converted to 5-(2-quinolyl)tetrabenzoporphyrin. The latter, when interacting with cobalt(II), copper(II) and manganese(II) chlorides in DMF, forms the corresponding metal complexes. The composition and structure of the obtained compounds were confirmed by a complex of physicochemical methods of analysis. The results of quantum-chemical calculations of complexes by DFT and TD-DFT methods are presented. The first absorption bands in theoretical electronic spectra are assigned to the corresponding electronic transitions in molecules. All synthesized tetrabenzoporphyrins have catalytic activity in the electroreduction reaction of oxygen; the cobalt complex exhibits the greatest activity.

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T. A. Rumyantseva

Ivanovo State University of Chemistry and Technology

Author for correspondence.
Email: taisialeb@mail.ru
ORCID iD: 0000-0002-4110-0572
Russian Federation, Ivanovo, 153000

N. M. Berezina

Ivanovo State University of Chemistry and Technology

Email: taisialeb@mail.ru
ORCID iD: 0000-0003-1784-7091
Russian Federation, Ivanovo, 153000

M. I. Bazanov

Ivanovo State University of Chemistry and Technology

Email: taisialeb@mail.ru
ORCID iD: 0000-0003-0425-2021
Russian Federation, Ivanovo, 153000

N. E. Galanin

Ivanovo State University of Chemistry and Technology

Email: taisialeb@mail.ru
ORCID iD: 0000-0001-6117-167X
Russian Federation, Ivanovo, 153000

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Supplementary files

Supplementary Files
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2. Additional Materials
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3. Fig. 1. Electronic absorption spectra of porphyrin 1 (1) and complex 3 (2) in chloroform.

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4. Fig. 2. Electronic absorption spectra of complexes 4 (1), 5 (2) and 6 (3) in chloroform.

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5. Fig. 3. Forms and energies of frontier orbitals (eV) in molecules of complexes 3–6. ΔE = EHOMO – ELUMO, eV.

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6. Fig. 4. Calculated electronic absorption spectra of complexes 3 (a), 4 (b), 6 (c).

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7. Fig. 5. I–E curves for an electrode with complex 4 in an argon atmosphere (1) and with saturation of the electrolyte with oxygen (2).

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8. Scheme 1.

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9. Scheme 2.

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10. Scheme 3.

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