Darstellung von bis-hydrazonen über die reduktion von benzalazin

Phenyl- and Thienyl-Ended Symmetric Azomethines and Azines as Model Compounds for n-Channel Organic Field-Effect Transistors: An Electrochemical and Computational Study

“…In organic media radical anions of azomethines and azines have shown dimerization, ,, but 1,4-dimethyl-substituted azines undergo successive reduction to their radical anion and then dianion . In such cases, where no acidic azomethine proton is present, the formation of the radical anion is completely reversible.…”

“…For A2 the process is fully reversible even at low scan rates, as reported in the literature. 15 Dimer is in fact produced by one-electron reduction electrolysis of A1, 31 whereas the radical anion is stable in A2, obviously due to the methyl substitution. The same picture is observed for the thienyl-ended azines A3 and A4.…”

“…It is thus evident that reversibility is provided by methyl capping of the azine moieties. The one-electron reduction of A1 in aprotic medium produces the dimer, 31 and it is argued that the same reaction takes place also for the thiophene homologue A3.…”