Synthesis and Electrochemical Properties of Benzo[b]naphtho[2,3-e][1,4]dioxin-6,11-quinones and Their N, N′-Dicyano Quinone Diimine Derivatives

The reaction of 2,3-dichloro-1,4-naphthoquinone (1) and catechols 2 in pyridine affords a series of substituted benzo[b]naphtho[2,3-e][1,4]dioxin-6,1l-quinones 3. The latter compounds are transformed to the corresponding N, N′-dicyano quinone diimines 4, by treating them with N, N′-bis(trimethylsilyl)carbodiimide. The electrochemical studies of compounds of the type 3 and 4 in DMF and CH₂Cl₂, respectively, by means of cyclic voltammetry are reported. The experimental reduction potentials provide information on electron-electron repulsion in the dianionic states of 3 and 4, and hence on their potential use as acceptor components in charge-transfer complexes and organic conductors.