A new fullerene C60-didodecyloxy benzene dyad: An evidence for ground state electron transfer

Synthesis, complete spectroscopic characterization and cyclic voltammetric measurements of a new didodecyloxybenzene-C60 dyad is described. The dyad showed distinct ground state intramolecular charge transfer as predicted from molecular orbital calculations and complimented by absorption and fluorescence spectroscopic behavior along with cyclic voltammetric studies, in solvents of varying polarity. The ab initio B3LYP/3-21G(d) electronic structure calculations are indicative of a non-planar ground state structure, 8 kJ/mol lower in energy than the planar structure. A ∼13° dihedral angle between the benzene ring and the oxygen of the alkoxybenzene moieties of the dyad is attributed to the antibonding interactions associated with the HOMO components.