Electron Acceptors Based on α-Substituted Perylene Diimide (PDI) for Organic Solar Cells

被引:204
作者
Zhao, Donglin [1 ,2 ]
Wu, Qinghe [1 ,2 ]
Cai, Zhengxu [1 ,2 ]
Zheng, Tianyue [1 ,2 ]
Chen, Wei [3 ,4 ]
Lu, Jessica [1 ,2 ]
Yu, Luping [1 ,2 ]
机构
[1] Univ Chicago, Dept Chem, 929 East 57th St, Chicago, IL 60637 USA
[2] Univ Chicago, James Franck Inst, 929 East 57th St, Chicago, IL 60637 USA
[3] Argonne Natl Lab, Div Mat Sci, 9700 Cass Ave, Lemont, IL 60439 USA
[4] Univ Chicago, Inst Mol Engn, 5747 South Ellis Ave, Chicago, IL 60637 USA
基金
美国国家科学基金会;
关键词
POWER CONVERSION EFFICIENCY; NONFULLERENE ACCEPTORS; PYRENE DERIVATIVES; SMALL-MOLECULE; DONOR; GENERATION; FULLERENES; TRANSPORT; SINGLET; DESIGN;
D O I
10.1021/acs.chemmater.5b04570
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Perylene diimide (PDI) derivatives functionalized at the ortho-position (alpha PPID, alpha PBDT) were synthesized and used as electron acceptors in non-fullerene organic photovoltaic cells. Because of the good planarity and strong pi-stacking of ortho-functionalized PDI, the alpha PPID and alpha PBDT exhibit a strong tendency to form aggregates, which endow the materials with high electron mobility. The inverted OPVs employing alpha PDI-based compounds as the acceptors and PBT7-Th as the donor give the highest power conversion efficiency (PCE) values: 4.92% for alpha PBDT-based devices and 3.61% for alpha PPID-based devices, which are, respectively, 39% and 4% higher than that of their beta-substituted counterparts beta PBDT and beta PPID. Charge separation studies show more efficient exciton dissociation at interfaces between alpha PDI-based compounds and PTB7-Th. The results suggest that alpha-substituted PDI derivatives are more promising electron acceptors for organic photovoltaic (OPV) components than beta-isomers.
引用
收藏
页码:1139 / 1146
页数:8
相关论文
共 57 条
[1]   Design of New Electron Acceptor Materials for Organic Photovoltaics: Synthesis, Electron Transport, Photophysics, and Photovoltaic Properties of Oligothiophene-Functionalized Naphthalene Diimides [J].
Ahmed, Eilaf ;
Ren, Guoqiang ;
Kim, Felix S. ;
Hollenbeck, Emily C. ;
Jenekhe, Samson A. .
CHEMISTRY OF MATERIALS, 2011, 23 (20) :4563-4577
[2]   2,5,8,11-Tetraboronic Ester Perylenediimides: A Next Generation Building Block for Dye-Stuff Synthesis [J].
Battagliarin, Glauco ;
Li, Chen ;
Enkelmann, Volker ;
Muellen, Klaus .
ORGANIC LETTERS, 2011, 13 (12) :3012-3015
[3]   An Efficient Triple-Junction Polymer Solar Cell Having a Power Conversion Efficiency Exceeding 11% [J].
Chen, Chun-Chao ;
Chang, Wei-Hsuan ;
Yoshimura, Ken ;
Ohya, Kenichiro ;
You, Jingbi ;
Gao, Jing ;
Hong, Zirou ;
Yang, Yang .
ADVANCED MATERIALS, 2014, 26 (32) :5670-+
[4]   Photoluminescence and conductivity of self-assembled π-π stacks of perylene bisimide dyes [J].
Chen, Zhijian ;
Stepanenko, Vladimir ;
Dehm, Volker ;
Prins, Paulette ;
Siebbeles, Laurens D. A. ;
Seibt, Joachim ;
Marquetand, Philipp ;
Engel, Volker ;
Wuerthner, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) :436-449
[5]   Synthesis of 2-and 2,7-Functionalized Pyrene Derivatives: An Application of Selective C-H Borylation [J].
Crawford, Andrew G. ;
Liu, Zhiqiang ;
Mkhalid, Ibraheem A. I. ;
Thibault, Marie-Helene ;
Schwarz, Nicolle ;
Alcaraz, Gilles ;
Steffen, Andreas ;
Collings, Jonathan C. ;
Batsanov, Andrei S. ;
Howard, Judith A. K. ;
Marder, Todd B. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) :5022-5035
[6]   Polymer-Fullerene Bulk-Heterojunction Solar Cells [J].
Dennler, Gilles ;
Scharber, Markus C. ;
Brabec, Christoph J. .
ADVANCED MATERIALS, 2009, 21 (13) :1323-1338
[7]   Recent advances of non-fullerene, small molecular acceptors for solution processed bulk heterojunction solar cells [J].
Eftaiha, Ala'a F. ;
Sun, Jon-Paul ;
Hill, Ian G. ;
Welch, Gregory C. .
JOURNAL OF MATERIALS CHEMISTRY A, 2014, 2 (05) :1201-1213
[8]   Polymer donor-polymer acceptor (all-polymer) solar cells [J].
Facchetti, Antonio .
MATERIALS TODAY, 2013, 16 (04) :123-132
[9]   PHOTOCHEMISTRY OF 3,4,9,10-PERYLENETETRACARBOXYLIC DIANHYDRIDE DYES .3. SINGLET AND TRIPLET EXCITED-STATE PROPERTIES OF THE BIS(2,5-DI-TERT-BUTYLPHENYL)IMIDE DERIVATIVE [J].
FORD, WE ;
KAMAT, PV .
JOURNAL OF PHYSICAL CHEMISTRY, 1987, 91 (25) :6373-6380
[10]  
Frisch MJ, 2013, Gaussian 09