Supramolecular triads bearing porphyrin and fullerene via ‘two-point’ binding involving coordination and hydrogen bonding

Supramolecular triads composed of fullerene (C60) as primary electron acceptor, zinc porphyrin (ZnP) as primary electron donor, and either a ferrocene (Fc), or N,N-dimethylaminophenyl (DMA), or N,N-diphenylaminophenyl (DPA) entity as a second electron donor were constructed via a ‘two-point’ binding motif involving axial coordination and hydrogen bonding. The B3LYP/3-21G(*) optimized structures revealed disposition of the three entities of the triads in a triangular fashion. The redox behavior of the different components was studied using cyclic voltammetry in o-dichlorobenzene containing 0.1 M (n-C4H9)4NClO4. The oxidation potentials of the second electron donor followed the trend: Fc