Syntheses, electrochemistry and molecular modeling of N,N′-dicyanoquinonediimine (DCNQI) derivatives of substituted 1,4-anthracenediones: Precursors for organic metals

Article abstract of DOI:10.1016/S0040-4020(01)80405-1

The title compounds (10) have been obtained from the corresponding 1,4-anthracenedione derivatives (3), prepared by different synthetic routes, by reaction with bis(trimethylsilyl) carbodiimide (BTC). The cyclic voltammetry of these compounds (3 and 10) reveals the presence of two reduction waves to the corresponding anion-radical and dianion. The acceptor ability of compounds 10 can be modulated by the presence of substituents on the DCNQI ring. The syn/anti isomers have been studied by molecular mechanics and the results are in good agreement with the ¹H-NMR high resolution spectral data.