Diels-Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60

Diels-Alder reaction of endocyclic, acyclic 1,3-dienes or (hetero) o-quitiodiinethanes with the dienophilic fullerene C-60 is presented as an efficient tool for linking electroactive units giving rise to systems where both the donor and C-60 partners take up well defined volumes and orientations with respect to one another. While porphyrin is the most frequently used electron donor in artificial photosynthetic models, C-60-based tetrathiafulvalene (TTF) or pi-conjugated oligomer adducts remain interesting candidates for the preparation of photovoltaic devices. In this account, we focus on the use of the Diels-Alder cycloaddition and its use in the synthesis of TTF-C-60 dyads, (TTF)(n)-C-60 polyads and C-60-TTF-C-60 dumbbells as part of ongoing research into materials which display efficient photo-induced electron transfer.