通过邻位和湾区位置连接的联二萘二亚胺铋的光学和电化学性质比较

Comparison of the Optical and Electrochemical Properties of Bi(perylene diimide)s Linked through Ortho and Bay Positions.

作者信息

Fan Yeli, Ziabrev Kostiantyn, Zhang Siyuan, Lin Baoping, Barlow Stephen, Marder Seth R

机构信息

School of Chemistry and Chemical Engineering, Southeast University, Nanjing, Jiangsu 211189, P. R. China.

Center for Organic Photonics and Electronics and School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, United States.

出版信息

ACS Omega. 2017 Feb 3;2(2):377-385. doi: 10.1021/acsomega.6b00537. eCollection 2017 Feb 28.

The Ullmann homocoupling of 2-bromo-perylene diimides (PDIs) gave [2,2'-biperylene]-3,4:9,10:3',4':9',10'-tetrakis(dicarboximide)s, 2,2'-bi(PDI)s, and the Suzuki coupling of a PDI-2-boronic ester and a 1-bromo-PDI gave a [1,2'-biperylene]-3,4:9,10:3',4':9',10'-tetrakis(dicarboximide), 1,2'-bi(PDI). These were compared with [1,1'-biperylene]-3,4:9,10:3',4':9',10'-tetrakis(dicarboximide)s, 1,1'-bi(PDI)s. Solution absorption spectra suggest that the PDIs in 2,2'-bi(PDI)s are more planar and less strongly coupled than those in 1,1'-bi(PDI)s, which is consistent with density functional theory calculations. 2,2'-Bi(PDI)s are less easily reduced than 1,1'- and 1,2'-bi(PDI)s by ca. 70-90 mV. Bulk heterojunction organic solar cells incorporating a 2,2'-bi(PDI) acceptor behaved similarly to those employing its 1,1'-bi(PDI) analogue.

2-溴苝二酰亚胺（PDIs）的乌尔曼自偶联反应生成了[2,2'-联苝]-3,4:9,10:3',4':9',10'-四羧酸二酰亚胺、2,2'-联（PDI），而PDI-2-硼酸酯与1-溴-PDI的铃木偶联反应生成了[1,2'-联苝]-3,4:9,10:3',4':9',10'-四羧酸二酰亚胺、1,2'-联（PDI）。将这些产物与[1,1'-联苝]-3,4:9,10:3',4':9',10'-四羧酸二酰亚胺、1,1'-联（PDI）进行了比较。溶液吸收光谱表明，2,2'-联（PDI）中的PDIs比1,1'-联（PDI）中的PDIs更平面化且耦合作用更弱，这与密度泛函理论计算结果一致。2,2'-联（PDI）比1,1'-和1,2'-联（PDI）更难被还原，约低70 - 90 mV。包含2,2'-联（PDI）受体的本体异质结有机太阳能电池的性能与其1,1'-联（PDI）类似物的性能相似。