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以3,4,9,10-苝四酸二酐为原料,通过在分子两端芳香环(bay位)分别连接2-甲氧基乙氧基和硝基,合成了两个不对称苝酰亚胺小分子N,N’-二(2-乙基己基)-1-(2-甲氧基乙氧基)-7-硝基-3,4,9,10-苝四羧酸二酰亚胺(Ⅲ)和N,N’-二(2-乙基己基)-1-(2-甲氧基乙氧基)-6,7-二硝基-3,4,9,10-苝四羧酸二酰亚胺(Ⅳ)。利用1HNMR,13CNMR和MS对其结构进行了表征。通过密度泛函理论计算优化了分子空间立体构象、扭曲结构和电子云分布;紫外-可见吸收光谱结果表明,Ⅲ和Ⅳ的最大吸收峰红移至559和572 nm,半峰宽变宽,为104和112 nm;经循环伏安(CV)测试估算,分子Ⅲ和Ⅳ的HOMO、LUMO能级分别为-5.85、-3.55 e V和-5.87、-3.62 e V;在相对湿度为50%的大气环境中,Ⅲ和Ⅳ分别与窄带隙聚合物(PTB7-Th)共混构建了有机太阳能电池器件,Ⅲ与PTB7-Th共混时对应的短路电流密度Jsc=3.6 m A/cm2,开路电压Voc=0.30 V,填充因子FF=0.40,光电转换效率η=0.42%;Ⅳ与PTB7-Th共混时对应的Jsc=4.00 m A/cm2,Voc=0.25 V,FF=0.41,η=0.40%。
Using 3,4,9,10-perylenetetracarboxylic dianhydride as starting material, two asymmetric peryl acrylates were synthesized by coupling 2-methoxyethoxy and nitro groups to the aromatic rings at both ends of the molecule Imine small molecule N, N’-bis (2-ethylhexyl) -1- (2-methoxyethoxy) -7-nitro-3,4,9,10-perylene tetracarboxylic diacyl Imine (III) and N, N’-bis (2-ethylhexyl) -1- (2- methoxyethoxy) -6,7-dinitro-3,4,9,10-perylene Tetracarboxylic diimide (IV). Its structure was characterized by 1HNMR, 13CNMR and MS. The three-dimensional conformation, the twisted structure and the electron cloud distribution were optimized by density functional theory calculations. The results of UV-vis absorption spectra showed that the maximum absorption peaks of Ⅲ and Ⅳ were red shifted to 559 and 572 nm, 104 and 112 nm, respectively. The cyclic voltammetry (CV) test estimated that the HOMO and LUMO energy levels of molecules III and IV were -5.85, -3.55 eV and -5.87, -3.62 eV, respectively; at relative humidity of 50% In the atmospheric environment, organic solar cells were fabricated by blending III and IV with narrow bandgap polymer (PTB7-Th), respectively. The corresponding short-circuit current density Jsc = 3.6 m A / cm2 when blended with PTB7-Th, Voc = 0.30 V, fill factor FF = 0.40 and photoelectric conversion efficiency η = 0.42%; Jsc = 4.00 m A / cm2, Voc = 0.25 V, FF = 0.41 and η = 0.40% when Ⅳ and PTB7- .