A Redox Switchable Dihydrobenzo[b]pyrazine Push-Pull System

The synthesis and spectroscopic properties of a dissymmetrically core-extended naphthalene diimides derived from o-phenylenediamine and cyanoethene dithiolate were explored. The push-pull nature of the peripheral substituents allows these naphthalene diimide dyes and their progenitors to display interesting photophysical and electrochemical properties, with the target system acting as a highly reversible and quantitative molecular switch with clear absorption and emission readouts based on chemical oxidation and reduction processes.