Details

Autor(en) / Beteiligte

• Kagilev, Alexey A.
• Morozov, Vladimir I.
• Zueva, Ekaterina M.
• Gafurov, Zufar N.
• Mikhailov, Ilya K.
• Kantyukov, Artyom O.
• Sakhapov, Il'yas F.
• Zhukova, Nataliya A.
• Kadyrova, Milyausha S.
• Mamedov, Vakhid A.
• Yakhvarov, Dmitry G.

Titel

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

Ist Teil von

• Journal of electroanalytical chemistry (Lausanne, Switzerland), 2022-09, Vol.921, p.116669, Article 116669

Ort / Verlag

Amsterdam: Elsevier B.V

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• [Display omitted] •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 NH 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 NH derivatives, the electrochemical reduction of N,N-dimethyl substituted derivative leads to radical anion and dianion species.