Facile Transformation of Perylene Tetracarboxylic Acid Dianhydride into Strong Donor–Acceptor Chromophores

Abstract

An efficient synthesis of 9,10-dibromo-1,6,7,12-tetrachloro-perylene-3,4-dicarboxylic acid monoimides from easily available 1,6,7,12-tetrachloro-perylene-3,4,9,10-tetracarboxylic acid dianhydride is reported. Therefrom, unprecedented perylene monoimides with pronounced donor-acceptor character were obtained via twofold aromatic amination. The halogen substituents in the 1,6,7,12-positions of perylene were removed under basic conditions. To the best of our knowledge, this is the first efficient synthetic route toward 9,10-doubly functionalized perylene-3,4-dicarboxylic acid monoimides.