Cyclic voltammetry of phenyl-substituted ethylenes in DMF and HMPA

Photochemical and electrochemical Z–E isomerization of 1,4-dialkoxy-2,5-bis[2-(thien-2-yl)ethenyl]benzene stereoisomers

“…Electrochemical properties of stilbene and its derivatives have also been intensively studied [9,10,[25][26][27][28][29], especially their reduction processes [9,[27][28][29]. The studies of the effect of Z-E isomerization on electrochemical properties have demonstrated [30] that the value of oxidation potential only fairly depends on the isomer type.…”

The electrochemical reduction of triphenylethylene in DMSO: a mechanistic study using mercury hemispherical microelectrodes

“…Other competing pathways have also been proposed including the regeneration mechanism [18] but no clear evidence of their operation has been observed [8,18].…”

“…Of the most relevance to the current study are those literature reports on the electrochemical reduction of tetraphenylethylene (TPE) and triphenylethylene (TriPE) [8,9,11,14,[17][18][19]. The electrochemical reduction of TPE has been studied in dimethylformamide (DMF) [8,14,19], hexamethylphosphoric acid triamide (HMPA) [8] and acetonitrile (MeCN) [11].…”

“…The electrochemical reduction of TPE has been studied in dimethylformamide (DMF) [8,14,19], hexamethylphosphoric acid triamide (HMPA) [8] and acetonitrile (MeCN) [11]. In DMF and MeCN, a single reversible two-electron reduction wave is observed, whereas in HMPA, two separate one-electron reduction waves displaying full reversibility are encountered.…”

“…For the electrochemical reduction of phenyl-substituted ethylenes in aprotic solvents in general, a reaction mechanism involving two sequential electron transfers accompanied by disproportionation of the radical anion following the scheme below is found to be in operation where the relative stability of the radical anion to protonation renders the pathway formally DISP2 [8][9][10][11][12][13][14].…”