First syntheses and electronic properties of (oligo)phenothiazine–C60 dyads

(Oligo)phenothiazine–C60 dyads 3 can be readily synthesized by a three-component condensation–cycloaddition of the corresponding (oligo)phenothiazinyl carbaldehydes 1, N-hexyl glycine (2), and C60. Cyclic voltammetry of 3 and reference compounds 4 shows that the phenothiazinyl moiety (donor) and the fullerene fragment (acceptor) are electronically decoupled in ground state. However, upon UV excitation the phenothiazinyl fluorescence is considerably quenched, presumably as a consequence of a charge separation by an intramolecular photo-induced electron transfer from phenothiazine to fullerene.