From the electrochemical generation of calix[4]arenedihydroquinone to the electrodeposition of calix[4]arenediquinone–calix[4]arenedihydroquinone assembly

The reduction of dimethoxycalix[4]arenediquinone in acetonitrile solution and the subsequent electrodeposition of calix[4]arenequinhydrone association on platinum electrode has been investigated. The formation of calix[4]arenedihydroquinone has been detected during the electrochemical generation calix[4]arenediquinone by the anodic oxidation of 5,11,17,23-tetra-tert-butyl-26,28-dimethoxycalix[4]arene-25,27-diol. By using cyclic voltammetry study, it is shown that in potentiodynamic and potentiostatic experiments, the electrochemical reduction of calix[4]arenediquinone leads to the formation of its corresponding calix[4]arenedihydroquinone and the subsequent organization of quinhydrone, which electrodeposits on the surface of disk electrode. In both solutions, the generation of protonated form of the reduced product has been detected by the appearance of two successive oxidation/reduction systems at about 0.7 and 1.2 vs SCE/V, respectively. Besides, the electroactive films showed during the anodic scanning one oxidation/reduction system at 1.0 vs SCE/V and two overlapped waves between 1.7 and 2.2 vs SCE/V. Two reduction/oxidation systems are also noted in the cathodic direction between −0.7 and −1.6 vs SCE/V.

► Electrochemical elaboration of calixarenediquinone and calixarenedihydroquinone deposit.
► The electroactivity of the donor–acceptor film indicates the presence of quinhydrone complex.
► This assumption is supported by the presence of strong absorption band.