Donor/acceptor fulleropyrrolidine triads

New C-60-based triads, constituted by a fulleropyrrolidine moiety and two d ifferent electroactive units [donor I-donor 2 (10, 15a,b), or donor 1-accep tor (17, 21)], have been synthesized by 1,3-dipolar cycloaddition reaction of azomethyne ylides to C-60 and further acylation reaction on the pyrrolid ine nitrogen. The electrochemical study reveals some electronic interaction between the redox-active chromophores. Triads bearing tetrathiafulvalene ( TTF) and ferrocene (Fe) (10) or pi-extended TTFs and Fe (15a,b) show reduct ion potentials for the C-60 moiety which are cathodically shifted in compar ison to the parent C-60 In contrast, triads endowed with Fe and anthraquino ne (AQ) (17) or Fe and tetracyanoanthraquinodimethane (TCAQ) (21) present r eduction potentials for the C-60 moiety similar to C-60 Fluorescence experi ments and time-resolved transient absorption spectroscopy reveal intramolec ular electron transfer (ET) processes from the stronger electron donor (i.e ., TTF or extended TTF) to the fullerene singlet excited state, rather than from the poorer ferrocene donor in 10, 15a,b. No evidence for a subsequent ET from ferrocene to TTF.+ or pi-extended TTF.+ was observed.