Taming C₆₀fullerene: tuning intramolecular photoinduced electron transfer process with subphthalocyanines

Abstract

Two subphthalocyanine-C₆₀ conjugates have been prepared by means of the 1,3-dipolar cycloaddition reaction of (perfluoro) or hexa(pentylsulfonyl) electron deficient subphthalocyanines to C₆₀. Comprehensive assays regarding the electronic features - in the ground and excited state - of the resulting conjugates revealed energy and electron transfer processes upon photoexcitation. Most important is the unambiguous evidence - in terms of time-resolved spectroscopy - of an ultrafast oxidative electron transfer evolving from C₆₀ to the photoexcited subphthalocyanines. This is, to the best of our knowledge, the first case of an intramolecular oxidation of C₆₀ within electron donor-acceptor conjugates by means of only photoexcitation.