Phenothiazine-Aromatic Hydrocarbon Acceptor Dyads as Photo-induced Electron Transfer Systems by Ugi Four-Component Reaction

A phenothiazinyl donor moiety can be covalently coupled to aromatic hydrocarbon acceptor units via Ugi four-component reaction in an efficient, rapid, and highly convergent fashion. These novel phenothiazine-acceptor dyads are electronically decoupled in the electronic ground state according to UV/Vis spectroscopy and cyclic voltammetry. In the excited state the inherent acceptor luminescence is substantially quenched. Calculations of the Gibbs energy of photo-induced electron transfer from readily available UV/Vis spectroscopic and cyclovoltammetric data according to the Weller approximation rationalizes the feasibility of the reductive electron transfer from phenothiazine to the aromatic hydrocarbon upon photoexcitation.