Practical Preparation of Octa- and Tetrabromoperylene Diimides and Derivatives Thereof

Abstract

A mild synthesis of fully brominated perylene dianhydride and diimides in one step from easily available unsubstituted precursors is presented. The partial reduction of ortho-bromo substituents with hydrazine hydrate allowed for a gram-scale synthesis of a valuable intermediate, 1,6,7,12-tetrabromoperylene diimide. Several new twisted fully core-substituted perylene diimide derivatives having sulfur, nitrogen, or oxygen substituents were synthesized using regioselective nucleophilic substitution reactions.