Facile synthesis of an isolable and ambient stable bay-substituted perylene diimide radical anion salt and its optical response to base–acid and metal ions

Abstract

An isolable and ambient stable bay-substituted perylene diimide adical anion salt was straightforwardly synthesized by base catalysis reduction of N,N-diethylhexyl-1,7-di(pentafluoro-phenoxyl) perylene diimide (DFPDI) in polar solvents, such as acetone, DMF, DMSO, NMP in yields of 48.7 %. Elemental analysis and 1H NMR, 13C NMR and EPR were carried out to confirm the formation of the compounds. Solvent-dependent cyclic voltammetries revealed the only condition for generating DFPDI radical anion in polar solvents—the reduction potential (DFPDI/DFPDI−) is more positive than −0.36 V (vs. Ag/AgCl). Redox studies revealed that DFPDI radical anion was not only ambient stable to moderate oxidants air (O2) and moisture for prolonged existence but also sensitive to strong oxidants-acid H+ and strong oxidization metal ions with low limit value.