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Through Bond Mechanism Versus Exciplex Formation in the Photochemistry of Fullerene / Ferrocene Donor-Bridge-Acceptor Dyads

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A systematic fluorescence and flash photolytic investigation of a series of covalently linked fullerene / ferrocene based donor-bridge-acceptor dyads is reported as a function of the nature of the bridge between the donor site and acceptor site. The fluorescence of the investigated dyads 2 (Φrel = 0.17 x 10-4), 3 (Φrel = 0.78 x 10-4), 4 (Φrel = 1.5 x 10-4), 5 (Φrel = 0.7 x 10-4), and 6 (Φrel = 2.9 x 10-4) were substantially quenched, relative to N-methyl fulleropyrrolidine (1) (Φrel = 6.0 x 10-4). Photolysis of N-methyl fulleropyrrolidine (1) in toluene revealed formation of the excited singlet state which was followed by a rapid intersystem crossing to the excited triplet state. On the other hand, the fate of the excited singlet state of 2, 3, 4, 5, and 6 was found to be governed by rapid intramolecular quenching, with rate constants of 28 x 109 S-1, 6.9 x 109 s-1, and 3.4 x 109 s-1, 14 x 109 s-1, 2.3 x 109 s-1 respectively. The electron transfer process and the charge separation were confirmed by monitoring the characteristic π-radical anion bands at λmax = 400 and 1055 nm in degassed benzonitrile with τ1/2 = 1.8 μs (3) and 2.5 μs(4).

Affiliations: 1: Radiation Laboratory, University of Notre Dame, Notre Dame, IN 46656, U.S.A.; 2: Centro Meccanismi di Reazioni Organiche del CNR, Dipartimento di Chimica Organica, Via Marzolo 1, 35131 Padova, ITALY; 3: Dipartimento di Scienze Farmaceutiche, Universitadi Trieste Piazzale Europa 1, 3412 Trieste, ITALY


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