Taming C ₆₀ fullerene: tuning intramolecular photoinduced electron transfer process with subphthalocyanines†

Abstract

Two subphthalocyanine–C ₆₀ fullerene electron donor–acceptor conjugates have been prepared from electron deficient subphthalocyanines and C ₆₀, with evidence of an ultrafast oxidative electron transfer from C ₆₀ to the subphthalocyanines.

Abstract

Two subphthalocyanine–C ₆₀ conjugates have been prepared by means of the 1,3-dipolar cycloaddition reaction of (perfluoro) or hexa(pentylsulfonyl) electron deficient subphthalocyanines to C ₆₀. 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 C ₆₀ to the photoexcited subphthalocyanines. This is, to the best of our knowledge, the first case of an intramolecular oxidation of C ₆₀ within electron donor–acceptor conjugates by means of only photoexcitation.

Notes

†Electronic supplementary information (ESI) available. CCDC 1014106. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00223k