Reversible Redox Systems, LXII . 2,3‐Disubstituted 1,4‐Benzoquinones and Their N,N′ ‐dicyanimines: Syntheses, Physical Properties, and CT Complexes with TTF

Synthesis, redox potentials, and AM1 calculations for 2,3‐disubstituted 1,4‐benzoquinones 3a–3j are described together with those of N,N′ ‐dicyanimines (DCNQIs) 4 . All data compare well with the corresponding 2,5‐disubstituted derivatives, except R 1 ,R 2 = OMe, SMe. The special effect of these groups is discussed on the basis of low energy out of plane conformers. All DCNQIs 4 occur as syn isomers with respect to the =NCN groups except 4d , where the five membered ring formed with R 1 ,R 2 = −[CH 2 ] 3 – forms 20% anti ‐ 4d in solution. All DNCQIs form CT complexes with TTF (derivatives) with powder conductivities of 10 −1 to 10 −3 Scm −1 .