SYNTHESIS OF NOVEL CHLOROSUBSTITUTED N,N-'-DICYANOQUINONEDIIMINES - FORMATION OF CHARGE-TRANSFER COMPLEXES AND COPPER RADICAL-ANION SALTS

Novel chloro-substituted N,N'-dicyanoquinonediimines (DCNQIs) (5) have been synthesized from the corresponding quinones (4) by reaction with bis(trimethylsilyl)carbodiimide (BTC) and titanium tetrachloride. Cyc lic voltammetry (CV) measurements of the prepared DCNQIs (5) exhibited the presence of two one-electron reversible reduction waves to the co rresponding radical anion and dianion. The first reduction potential r evealed a better acceptor ability of compounds 5 than the parent DCNQI , these values being strongly dependent on the presence of chlorine at oms. The H-1 NMR high resolution spectral data showed, when possible, the presence of the syn-anti isomers in these compounds (5). Charge tr ansfer complexes (6) of the novel DCNQIs (5) with the donor tetrathiaf ulvalene (TTF) and also the copper radical-anion salts (7) have been o btained. Room temperature conductivities of the charge transfer comple xes (6) and charge transfer salts (7) were measured and the temperatur e dependence exhibited a semiconducting behaviour.