REVERSIBLE REDOX SYSTEM .62. 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-disubstitute d 1,4-benzoquinones 3a-3j are described together with those of N,N'-di cyanimines (DCNQIs) 4. All data compare well with the corresponding 2, 5-disubstituted derivatives, except R-1,R-2 = OMe, SMe. The special ef fect of these groups is discussed on the basis of low energy out of pl ane conformers. All DCNQIs 4 occur as syn isomers with respect to the =N-CN groups except 4d, where the five membered ring formed with R-1,R -2 = -[CH2](3)- forms 20% anti-4d in solution. All DNCQIs form CT comp lexes with TTF (derivatives) with powder conductivities of 10(-1) to 1 0(-3) Scm(-1).