An efficient and high yield protocol for the synthesis of 1,6,9,12-tetrabromo-3,4,9,10-tetracarboxylic acid perylenebisimides and anhydrides using N-bromosuccinamide

Abstract

Due to the importance of tetrabromo perylene bisimides, in this letter, we report an efficient protocol for the synthesis of various bromo derivatives particularly, 1,6,7,12-tetrabromoperylene-3,4,9,10-tetracarboxylic acid bisimides (perylene bisimides, or PBIs) in high yield with short reaction time using N-bromosuccinimide (NBS) in Conc. H2SO4. By controlling the reaction time, mono, di, tri, and tetrabromo PBI derivatives could be isolated in moderate to good yield. Under the same condition, perylenebisanhydride brominated with NBS afforded tetrabromoperylenebisanhydride quantitatively in a short reaction time.