Electron Transfer in Reaction of 12H-Quinoxalino[2,3-b]phenoxazines with π-Acceptors

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Abstract

Using the reaction of 2,4-di-(tert-butyl)-12-(4-methoxyphenyl)-10-methoxy-12H-quinoxalino[2,3-b]phenoxazine with π-electron acceptors such as tetracyanoquinodimethane and 3,6-di-(tert-butyl)-o-quinone) as an example it was shown that derivatives of this N,O-pentaheterocyclic system are effective electron donors that, under mild conditions, carry out electron transfer reactions with the formation of stable cation and anion radical structures.

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About the authors

E. P. Ivakhnenko

Institute of Physical and Organic Chemistry, Southern Federal University

Author for correspondence.
Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0003-0338-6466
Russian Federation, Rostov-on-Don, 344091

P. A. Knyazev

Institute of Physical and Organic Chemistry, Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0001-6627-8329
Russian Federation, Rostov-on-Don, 344091

N. I. Makarova

Institute of Physical and Organic Chemistry, Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0002-7196-9842
Russian Federation, Rostov-on-Don, 344091

O. P. Demidov

North-Caucasus Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0002-3586-0487
Russian Federation, Stavropol, 355017

A. G. Starikov

Institute of Physical and Organic Chemistry, Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0002-5613-6308
Russian Federation, Rostov-on-Don, 344091

V. I. Minkin

Institute of Physical and Organic Chemistry, Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0001-6096-503X
Russian Federation, Rostov-on-Don, 344091

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Supplementary files

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2. Fig. 1. Experimental (1) and theoretical (2) EPR spectra of the TCNQ anion radical in complex 2 (CHCl3, g = 2.000, a4N = 1.05 Gs, a4H = 1.46 Gs).

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3. Fig. 2. The molecular structure of complex 2 (a) and the packaging in the crystal (b).

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4. 3. Geometric characteristics of the N14-H and N7-H isomers calculated by the DFT method [B3LYP/6-311G++(d,p)]. Bond lengths are given in Å, hydrogen atoms, with the exception of the determining protonation site, are not shown. The RSA data is shown in red font.

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5. Fig. 4. Evolution of the electronic absorption spectra depending on the molar fraction of TCNQ in the solution of the compound QOPO 1 (acetonitrile, c = 4·10-5 M, l = 1 cm, T = 293 K).

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6. Fig. 5. Experimental (1) and theoretical (2) EPR spectra of the QOPO 3 radical cation (CH3COOH, PbO2, g = 2.000, aN = 7.15 Gs, aH = 3.44 Gs).

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7. 6. Experimental (1) and calculated (2) EPR spectra of radical 4 (CF3COOH, toluene, g = 2.002, aN = 7.59 Gs, aH = 4.64 Gs, aH = 3.79 Gs, a2H = 3.54 Gs, aH = 1.52 Gs).

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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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