A simple protocol for the synthesis of perylene bisimides from perylene tetracarboxylic dianhydride

Abstract

Perylene bisimides are highly attractive polycyclic aromatic hydrocarbons due to their photostability associated to unique and characteristic photochemical properties. They have been widely used for analytical purposes, despite the hydrophobicity of most of these compounds. The ring substitution pattern plays an important role in fine-tuning the physicochemical properties that govern solubility and aggregation. In this work, a selection of perylene bisimides were prepared from the reaction of perylenetetracarboxylic dianhydride with α-amino acids or primary aliphatic and aromatic amines. These molecules were obtained in good yield by a simple synthetic protocol based on the use of imidazole as a green solvent and avoiding the need for complex purification methods, a major advantage for future applications. Functionalization of the exocyclic substituent can also be performed and was exemplified by the incorporation of the maleimide and anthraquinone moieties.