Efficient Tuning of LUMO Levels of 2,5,8,11-Substituted Perylenediimides via Copper Catalyzed Reactions

Via one-step copper catalyzed procedures it was possible to synthesize 2,5,8,11-tetrabromo, tetrachloro, and tetracyano derivatives of perylenediimides. Characterization of optical and electrochemical properties of these materials proves substantial enhancement of the electron affinity, with a LUMO level as low as -4.4 eV in the case of the tetracyano perylenediimide.