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Two new, rigid donor−bridge−C60(acceptor) dyads are presented. In one system (C60[3]TMPD) a 3-σ-bond bridge separates the fullerene from a powerful tetraalkyl-p-phenylenediamine donor; in the other (C60[11]DMA) the bridge comprises an extended array of 11 bonds, while the donor unit is a dimethylaniline group. Photoexcitation of the 3-bond system induces fast (kcs ≥ 1.6 × 1010 s-1) and virtually complete intramolecular charge separation, irrespective of solvent polarity. It is concluded that this charge separation occurs under nearly “optimal” conditions. Charge recombination, however, is also very fast, preventing the detection of the charge-separated state on a nanosecond time scale. For the 11-bond system, photoinduced charge separation only occurs in polar solvents, reaching kcs = 5.5 × 109 s-1 in benzonitrile, which still implies a charge separation yield of ∼90%. Interestingly, charge recombination is now slowed down considerably, thereby allowing easy detection of the “giant dipolar” charge-separat...

Photoinduced Electron Transfer to C60 across Extended 3- and 11-Bond Hydrocarbon Bridges: Creation of a Long-Lived Charge-Separated State

Photoinduced Electron Transfer to C₆₀ across Extended 3- and 11-Bond Hydrocarbon Bridges: Creation of a Long-Lived Charge-Separated State