Synthesis and Redox Properties of Azino-Chalcogenoazafulvalenes: an Entry to Electroactive Azino Macrocyclic Compounds

The synthesis of a series of dimers containing two redox active moieties, such as azino-chalcogenoazafulvalenes, connected through one or two non conjugated spacer group is reported. Various heterocycles have been used to build these donor molecules incorporating an azino spacer group between two thiazole moieties or a thiazole core and a selenazole one or two selenazole cores or a thiazole and a dithiole moiety. Cyclic voltammetry experiments have evidenced the influence of the nature of the heterocycle on the donating ability of these dimers. Moreover, sizable intramolecular interactions between the two electroactive moieties are observed depending on the length and the number of the non conjugated spacer group.