Design, synthesis, and electrochemical studies of a new [60] fullerene pyrrolidine as a precursor for the construction of supramolecular systems

Abstract

One of the challenges in fullerene chemistry is to prepare derivatives soluble in common solvents to study their chemical and physical properties in solution. In this context, a new highly soluble fullerene adduct was synthesized by the cycloaddition of a hydrazone-aldehyde derivative, which is prepared from the condensation of pyridincarboxaldehyde and pyridinhydrazine derivatives, and C60 in the presence of N-octyl glycine. The hydrazone derivative acting as a 1,3-dipole and [60] fullerene as a dipolarophile yielded adduct 7 with a 32% yield. The synthesized compounds were characterized by nuclear magnetic resonance (NMR) spectroscopy (1H, 13C, and COSY), elemental analysis, and mass spectrometry. The electronic properties of the fullerene adduct 7 were analyzed by UV-Vis spectroscopy in toluene and compared to those of [60]fullerene. The electrochemical properties of the fulleropyrrolidine were studied using cyclic and square wave voltammetry in tetrahydrofuran (THF) showing three reduction peaks at -1.11, -1.70, and -2.28 V, which are cathodically shifted when compared to [60]fullerene.