Tuning The Lumo Levels Of Z-Shaped Perylene Diimide Via Stepwise Cyanation

The central dogma in constructing organic electron acceptors is to attach electron-withdrawing groups to polycyclic aromatic hydrocarbons. Yet, the full potentials of many organic acceptors were never realized due to synthetic obstacles. By combining the Wittig-Knoevenagel benzannulation, the Pd(0)-catalyzed cyanation, and nucleophilic addition/oxidation cyanation, six polynitrile Z-shaped perylene diimide were synthesized. These stable and soluble electron acceptors possess LUMO energy levels comparable with those of benchmark compounds. Electro-chemical investigation reveals that each additional nitrile group reduces the LUMO energy by 0.2 eV.