Amphoteric tetrazole-substituted eleven-ring-fused acene derivatives with multiple fluorescent protonation states

Abstract

We synthesized novel tetrazole-substituted diacenaphthoanthracenediimides 2 by azide cycloaddition to the corresponding cyano-substituted precursors. Reversible protonation/deprotonation of the tetrazole moieties provides distinct fluorescent species with photoluminescence quantum yields of 12–34%. The facile deprotonation of 2 enables its processing in non-halogenated solvents (alcohol).