The Systhesis And Application Properties Of Ambient Stable Perylene Diimides Radicalanions

Perylene diimide radical anion salts had near-infrared absorbance and high electron mobility potentially applied in the organic semiconductor materials.However,the perylene diimide radical anions are prone to react with solvents,oxygen and so on,thereby,the preparation of stable perylene diimide radical anions has been a challenge of science.An isolable and ambient stable bay-substituted perylene diimide adical anion salt was firstly synthesized by base catalysis reduction of N,N-diethylhexyl-1,7-di(pentafluoro-phenoxyl)perylene diimide.Infrared absorption spectroscopy,fluorescence spectroscopy,1H NMR,13 C NMR,EPR,spectroelectro-chemical determined its chemical structure.The effects of temperature and solvent on preparation of perylene diimide radical ion salt were also investigated.The effect of air,acid-base and metal ions on radical anions stablitity was investigated through UV-vis absorption spectra.N,N’-diethylhexyl-perylene diimide,N,N’-diethylhexyl-1,7-dibromo-perylene diimide,N,N’-diethylhexyl-1,7-p-tert-butylphenoxy-perylene diimide,N,N’-diethyl hexyl-1,7-p-hydroxypyridine-perylene diimide were used to study the effect of electron withdrawing substituents and electron-donating substituents on perylene diimide reduction potentials and their radical anion salt preparation,air stability,metal ion sensitivity.Bay electron-withdrawing groups of perylene diimides make their one-electron reduction potentials more positive and higher electron affinity that were beneficial to development of radical anions but bay electron-donating groups make their one-electron reduction potentials more negative and low electron affinity that were beneficial to stability of radical anion salts.Straightforwardly synthesized graphene oxide sheet-immobilized and stabilized perylene diimide radical anion salt exhibited not only ambient stability in air but sensitivity to strong oxidation metal ions,solvatochromism,improved charge mobility.