Novel fullerene-based dyads: synthesis and electron-transfer processes

Electron- and energy transfer processes involving C-60 has been the subject of an increasing number of works. So far, C-60 has been used unmodified in heterogeneous mixtures with conducting polymers or strong donors like phthalocyanines, or it has been chemically modified to improve its miscibility with conducting polymers or to attach it covalently to a donor, building dyads or triads of various types. The "organic chemistry of fullerenes", in fact, offers the advantage of combining the properties of C-60 with those of other classes of interesting materials such as electro- or photoactive species. We have recently developed a convenient way to functionalize C-60 using azomethine ylide cycloaddition. This reaction is very easily performed, starting from any alfa-amino acid and potentially any aldehyde. Using these approach, several dyads and triads have been prepared. We report here the synthesis, the electrochemical and photophysical properties of a novel fullerene-porphyrin dyad in which the fullerene has been attached to the porphyrin donor through metal coordination.