水溶性苝酰亚胺化合物电子转移与长寿命自由基阴离子的生成

Electron transfer of water-soluble perylene diimide compound and long-life radical anion generation

利用紫外可见吸收光谱研究了一种结构新颖的以聚乙二醇(polyethylene glycol,PEG)链为取代基的水溶性苝酰亚胺化合物N,N’-二(聚乙二醇)-1-(4-巯基苯)苝酰亚胺(N,N’-Di(polyethylene glycol)-1-(4-mercaptobenzene)-perylene-3,4,9,10-tetracarboxylic diimide,BFL)的聚集行为,溶剂极性、表面活性剂对聚集行为有显著影响。结果表明:在水溶液中BFL在530 nm只出现一个与单体聚集体比例相关的特征峰;浓度增加,溶液中聚集体比例增加不明显;而有机溶剂和表面活性剂能够分散化合物,明显提高单体的数量。在水溶液中硫化钠使BFL发生电子转移反应,能够捕捉到超长寿命的中间产物一价阴离子自由基,之后BFL进一步被还原为二价阴离子。这种能够在还原反应中产生超长寿命自由基的特性使BFL成为优异的n型材料。

A novel water-soluble perylene diimide compound,N,N'-di(polyethylene glycol)-1-(4-mercaptobenzene)-perylene-3,4,9,10-tetracarboxylic diimide(BFL),was synthesized by introducing PEG chains.Solvent-and temperature-dependent visible spectra were investigated and aggregation states were analysed.The results show that BFL in aqueous solution has only one absorption band at 530 nm,which is related to the ratio of monomer/aggregates.However,the change in the monomer/aggregates ratio with increasing concentration of BFL molecules is not obvious.Organic solvents and surfactants can disperse the compound,thereby significantly increasing the amount of the monomer.BFL can react with sodium sulfide in water;BFL is first reduced to anion radicals and then to dianions.The ability to produce a long-life free radical in the reduction reaction will make the BFL an excellent n-type material.