Fullerene-Perylenediimide (C(60)-PDI) Based Systems: An Overview and Synthesis of a Versatile Platform for Their Anchor Engineering

An overview of the different covalent bonding synthetic strategies of two electron acceptors leading to fullerene-perylenediimide (C(60)-PDI)-based systems, essentially dyads and triads, is presented, as well as their more important applications. To go further in the development of such electron and photoactive assemblies, an original aromatic platform 5-benzyloxy-3-formylbenzoic acid was synthesized to graft both the PDI dye and the fullerene C(60). This new C(60)-PDI dyad exhibits a free anchoring phenolic function that could be used to attach a third electro- and photoactive unit to study cascade electron and/or energy transfer processes or to obtain unprecedented side-chain polymers in which the C(60)-PDI dyads are attached as pendant moieties onto the main polymer chain. This C(60)-PDI dyad was fully characterized, and cyclic voltammetry showed the concomitant reduction process onto both C(60) and PDI moieties at identical potential. A quasi-quantitative quenching of fluorescence was demonstrated in this C(60)-PDI dyad, and an intramolecular energy transfer was suggested between these two units. After deprotection of the benzyloxy group, the free hydroxyl functional group of the platform was used as an anchor to reach a new side-chain methyl methacrylate-based polymer in which the PDI-C(60) dyad units are located as pendants of the main polymer chain. Such polymer which associates two complementary acceptors could find interesting applications in optoelectronics and in particular in organic solar cells.