Self anion radical induced breaking carbon–oxygen bond in bay area of perylene diimide, and nucleophilic substitution with SRN1 mechanism

Abstract Perylene diimide and its various derivatives tend to form their anion radicals after obtaining one electron, which will alter their chemical properties. Herein, we reported firstly synthesis of the unsymmetrically substituted perylene diimide in bay area using the degradation of the symmetrically substituted perylene diimide. The perylene diimide anion radical that is obtained by thermal electron transfer can induce breaking carbon-oxygen bond at bay area, and to form new perylene diimide derivative by nucleophilic substitution with SRN1 Mechanism. Experimental and theoretical simulation indicated that anion radical can promote the C–O bond breaking in this system.