Electrochemical properties of a liquid-crystalline mixed fullerene–ferrocene material and related species

The electrochemical properties of a fullerene–ferrocene liquid crystal are reported. The electrochemical study was carried out under strictly aprotic conditions: a total of seven reduction peaks were detected in the negative potential region, and two oxidation peaks in the positive potential one. Comparison of the data with those obtained from suitable model compounds (i.e., analogous fullerene- or ferrocene-free materials ) has allowed the assignment of all reduction and oxidation steps. The CV study evidenced the occurrence of a fast follow-up chemical reaction coupled to the third (at 25 °C) or fourth (at –60 °C) reduction of either <b>1</b> or <b>3</b>. Such a reaction, presumably related to the cleavage of one of the cyclopropane bonds, is quantitatively reversed upon re-oxidation. Conversely, under bulk electrolysis conditions (second reduction), the species undergo the retro-Bingel reaction, i.e. the irreversible removal of the bis(alkoxycarbonyl)methano adducts to give the parent C₆₀.