Synthesis, electrochemical properties and effect of substituents on π-extended TCNQ and DCNQI systems

Abstract The synthesis of novel π -extended TCNQ and DCNQI derivatives from the corresponding 1,4-anthraquinones is described. The cyclic voltammetric data reveal that both TCNQ-type and DCNQI-type acceptors present two one-electron reduction waves to the corresponding anion-radical and dianion. These novel 2,3-fused TCNQ and DCNQI π -extended systems are, according to the electrochemical values, better acceptors than the previously reported 2,3–5,6-fused TCNQ and DCNQI molecules. A good linear correlation between the first reduction potential of the substituted DCNQI-type derivatives versus the Hammett's σ 3 constant has been found.