Novel soluble and thermally-stable fullerene dyad containing perylene

A novel fullerene dyad C-60-P1 in which a perylene moiety is attached to C-60 through a pyrrolidine ring has been prepared by 1,3-dipolar cycloaddition of the azomethine ylides generated in situ from the corresponding aldehyde and sarcosine. Electrochemical and photophyscial studies of the dyad in solution have revealed that there is no significant ground-state electronic interaction between the covalently bonded perylene moiety and the fullerene. The photophysical investigations have also shown that there exists an effective photoinduced energy transfer from the perylene moiety to C-60. A photovoltaic device made with the dyad has confirmed that photoinduced electron transfer does take place within the dyad; however, the efficiency of the electron transfer is negligible relative to the energy transfer.