Journal of Electroanalytical Chemistry, volume 921, pages 116669

Electrochemical behaviour of 2,2′-bibenzimidazoles: Voltammetric, in situ UV–vis- and EPR-spectroelectrochemical and computational studies

Kagilev A. A. ^{1, 2}

Morozov V I ¹

Zueva Ekaterina M ^{1, 3}

Gafurov Zufar N ¹

Mikhailov I. K. ^{1, 2}

Kantyukov A. O. ^{1, 2}

Sakhapov Ilyas F. ¹

Zhukova Nataliya ¹

Kadyrova Milyausha S ¹

Mamedov V. A. ¹

Yakhvarov Dmitry ^{1, 2}

Hide authors affiliations Show authors affiliations: 3 affiliations

A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str. 8, 420088 Kazan, Russian Federation

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Kazan Scientific Center of the Russian Academy of Sciences

A.M. Butlerov Institute of Chemistry, Kazan Federal University, Kremlyovskaya str. 18, 420008 Kazan, Russian Federation |

Kazan National Research Technological University, Karl Marx str. 68, 420015 Kazan, Russian Federation |

Publication type: Journal Article

Publication date: 2022-09-01

Elsevier

Journal: Journal of Electroanalytical Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 4.5

ISSN: 15726657

DOI: 10.1016/j.jelechem.2022.116669

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General Chemical Engineering

Analytical Chemistry

Electrochemistry

Abstract

• The electrochemical properties of 2,2′-bibenzimidazole and its substituted analogues have been investigated by cyclic voltammetry, square-wave voltammetry and in situ UV–vis- and EPR-spectroelectrochemistry. • The nature of the formed in the electrochemical process radicals has been elucidated. • The formation of 2,2′- bibenzoimidazolylidene species and the mechanism of the electrochemical reduction process have been postulated. The electrochemical properties of 2,2′-bibenzimidazole and its substituted analogues 5,6-dimethyl-2,2′-bibenzimidazole, 5,5′,6,6′-tetramethyl-2,2′-bibenzimidazole as well as 1,1′-dimethyl-2,2′-bibenzimidazole were investigated by cyclic voltammetry (CV) and square-wave voltammetry (SWV) combined with mechanistic studies by means of in situ UV–vis- and EPR-spectroelectrochemistry. The data obtained for N H derivatives suggest the formation of 2,2′-bibenzoimidazolylidene species via ECEC reaction mechanism consisting of two successive one-electron transfers accompanied by proton migration. The resulting species undergo further one-electron reduction with the formation of stable anion-radicals, whose structures have been identified by in situ UV–vis- and EPR-spectroelectrochemical measurements and supported by the computational study using density functional theory (DFT) calculations. In contrast to N H derivatives, the electrochemical reduction of N,N -dimethyl substituted derivative leads to radical anion and dianion species.

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Journal of Molecular Structure	Journal of Molecular Structure, 4, 44.44% Journal of Molecular Structure 4 publications, 44.44%
Current Opinion in Electrochemistry	Current Opinion in Electrochemistry, 1, 11.11% Current Opinion in Electrochemistry 1 publication, 11.11%
Results in Chemistry	Results in Chemistry, 1, 11.11% Results in Chemistry 1 publication, 11.11%
Chemical Physics Impact	Chemical Physics Impact, 1, 11.11% Chemical Physics Impact 1 publication, 11.11%
Journal of Solid State Electrochemistry	Journal of Solid State Electrochemistry, 1, 11.11% Journal of Solid State Electrochemistry 1 publication, 11.11%
Heliyon	Heliyon, 1, 11.11% Heliyon 1 publication, 11.11%
	1 2 3 4

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Elsevier	Elsevier, 8, 88.89% Elsevier 8 publications, 88.89%
Springer Nature	Springer Nature, 1, 11.11% Springer Nature 1 publication, 11.11%
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Kagilev A. A. et al. Electrochemical behaviour of 2,2′-bibenzimidazoles: Voltammetric, in situ UV–vis- and EPR-spectroelectrochemical and computational studies // Journal of Electroanalytical Chemistry. 2022. Vol. 921. p. 116669.

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Kagilev A. A., Morozov V. I., Zueva E. M., Gafurov Z. N., Mikhailov I. K., Kantyukov A. O., Sakhapov I. F., Zhukova N., Kadyrova M. S., Mamedov V. A., Yakhvarov D. Electrochemical behaviour of 2,2′-bibenzimidazoles: Voltammetric, in situ UV–vis- and EPR-spectroelectrochemical and computational studies // Journal of Electroanalytical Chemistry. 2022. Vol. 921. p. 116669.

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RIS Copy

TY - JOUR

DO - 10.1016/j.jelechem.2022.116669

UR - https://doi.org/10.1016%2Fj.jelechem.2022.116669

TI - Electrochemical behaviour of 2,2′-bibenzimidazoles: Voltammetric, in situ UV–vis- and EPR-spectroelectrochemical and computational studies

T2 - Journal of Electroanalytical Chemistry

AU - Kagilev, A. A.

AU - Morozov, V I

AU - Zueva, Ekaterina M

AU - Gafurov, Zufar N

AU - Mikhailov, I. K.

AU - Kantyukov, A. O.

AU - Sakhapov, Ilyas F.

AU - Zhukova, Nataliya

AU - Kadyrova, Milyausha S

AU - Mamedov, V. A.

AU - Yakhvarov, Dmitry

PY - 2022

DA - 2022/09/01 00:00:00

PB - Elsevier

SP - 116669

VL - 921

SN - 1572-6657

ER -

BibTex

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@article{2022_Kagilev,

author = {A. A. Kagilev and V I Morozov and Ekaterina M Zueva and Zufar N Gafurov and I. K. Mikhailov and A. O. Kantyukov and Ilyas F. Sakhapov and Nataliya Zhukova and Milyausha S Kadyrova and V. A. Mamedov and Dmitry Yakhvarov},

title = {Electrochemical behaviour of 2,2′-bibenzimidazoles: Voltammetric, in situ UV–vis- and EPR-spectroelectrochemical and computational studies},

journal = {Journal of Electroanalytical Chemistry},

year = {2022},

volume = {921},

publisher = {Elsevier},

month = {sep},

url = {https://doi.org/10.1016%2Fj.jelechem.2022.116669},

pages = {116669},

doi = {10.1016/j.jelechem.2022.116669}

}

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Publisher

Elsevier

Journal

Journal of Electroanalytical Chemistry

Quartile SCImago

Quartile WOS

Impact factor

4.5

ISSN

15726657 (Print)

Labs

Laboratory of Organometallic and Coordination Compounds

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