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 R1,R2 = 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 =NCN groups except 4d, where the five membered ring formed with R1,R2 = −[CH2]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.