摘要
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%。
Two asymmetric nitryl substituted perylene diimide derivatives,N,N＇-di（ 2-ethylhexyl）-1-（ 2-methoxyethoxy）-7-nitryl-perylene-3,4,9,10-tertracarboxylic acid diimide（ Ⅲ） and N,N＇-di（ 2-ethylhexyl）-1-（ 2-methoxyethoxy）-6,7-dinitryl-perylene-3,4,9,10-tertracarboxylic acid diimide（ Ⅳ）,were successfully synthesized. They were characterized by1 HNMR,13CNMR and MS. The molecular stereoscopic conformation,the molecular twisted structure and distribution of electron cloud were also studied by density functional theory（ DFT） calculations. Additionally,the Ultraviolet-Visible absorption spectra（ UV-Vis） of the compounds were investigated. The results showed that the largest absorption band of compound Ⅲ occurred at 559 nm,and that of compound Ⅳ was at 572 nm,which displayed a full width at half maximum of 104 nm and 112 nm. The HOMO energy levels for compound Ⅲ and Ⅳwere-5. 85 e V and-5. 87 e V,respectively. And the corresponding LUMO energy levels were-3. 55 e V and-3. 62 e V. Finally,the organic solar cells were fabricated by using compounds Ⅲ and Ⅳblending with benzodithiophene-alt-polythiophene（ PTB7-Th） in atmospheric environment at a controlled relative humidity of 50%,respectively. The device based on compound Ⅲ gave a power conversion efficiency（ η） of 0. 42%,with short-circuit photocurrent density（ Jsc） of 3. 6 m A/cm2,open-circuit photovoltage（ Voc） of 0. 30 V,and fill factor（ FF） of 0. 40. While the device for compound Ⅳ achieved a power conversion efficiency of 0. 40%,with Jsc= 4. 00 m A/cm2,Voc= 0. 25 V,and FF = 0. 41.
作者
吴启超
丘海玲
谢博文
朱惠丹
张伟明
海杰峰
陆振欢
WU Qi-chao QIU Hai-ling XIE Bo-wen ZHU Hui-dan ZHANG Wei-ming HAI Jie-feng LU Zhen-huan(Guangxi Key Laboratory of Electrochemical and Magneto-chemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 54100, Guangxi , China)
出处
《精细化工》
EI
CAS
CSCD
北大核心
2017年第10期1180-1184,共5页
Fine Chemicals
基金
国家自然科学基金(21563007)
广西自然科学基金(2015GXNSFBA139021,2015GXNSFBA139228)
桂林理工大学博士科研启动基金
2016年国家级大学生创新创业训练计划项目(201610596017)~~
关键词
苝酰亚胺
小分子
偶极矩
光电性能
不对称电子云
有机太阳能电池
有机电化学与工业
perylene diimide
small molecule
dipole moment
photoelectric property
asymmetric electronic cloud
organic solar cells
electro-organic chemistry and industry
