Twisted terrylene dyes: synthesis and application in organic solar cells

被引:25
作者
Feng, Jiajing [1 ,2 ]
Liang, Ningning [1 ,2 ]
Jiang, Wei [1 ]
Meng, Dong [1 ,2 ]
Xin, Rui [3 ]
Xu, Bowei [1 ]
Zhang, Jianqi [4 ]
Wei, Zhixiang [4 ]
Hou, Jianhui [1 ]
Wang, Zhaohui [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, CAS Res Educ Ctr Excellence Mol Sci, Key Lab Organ Solids,Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Beijing Univ Chem Technol, State Key Lab Chem Resource Engn, Beijing 100029, Peoples R China
[4] Chinese Acad Sci, Natl Ctr Nanosci & Technol, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
PERYLENE BISIMIDE DYES; NON-FULLERENE-ACCEPTOR; ELECTRON-ACCEPTOR; PERFORMANCE; DIIMIDES; MOLECULE;
D O I
10.1039/c7qo00118e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two twisted terrylene diimides (TDIs), namely TDI2 and BTDI3, have been designed and synthesized. In comparison to monomeric TDI, their molecular geometries and optoelectronic properties have been systematically investigated. BTDI3, with a highly twisted 3D geometry, shows the best light-absorbing capability in the range of 500-700 nm and a suitable LUMO level. Simultaneously, a preliminary exploration of their photovoltaic performances was carried out. The optimized device based on PBDT-TS1/BTDI3 produces a power conversion efficiency (PCE) of 3.64%, demonstrating the potential of terrylene dyes in the photovoltaics field.
引用
收藏
页码:811 / 816
页数:6
相关论文
共 30 条
[1]   White-Light Emitting Hydrogen-Bonded Supramolecular Copolymers Based on π-Conjugated Oligomers [J].
Abbel, Robert ;
Grenier, Christophe ;
Pouderoijen, Maarten J. ;
Stouwdam, Jan W. ;
Leclere, Philippe E. L. G. ;
Sijbesma, Rint P. ;
Meijer, E. W. ;
Schenning, Albertus P. H. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :833-843
[2]   Ortho- vs Bay-Functionalization: A Comparative Study on Tetracyano-Terrylenediimides [J].
Battagliarin, Glauco ;
Puniredd, Sreenivasa Reddy ;
Stappert, Sebastian ;
Zajaczkowski, Wojciech ;
Wang, Suhao ;
Li, Chen ;
Pisula, Wojciech ;
Muellen, Klaus .
ADVANCED FUNCTIONAL MATERIALS, 2014, 24 (47) :7530-7537
[3]   Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors:: Studies on structural, electrochemical and charge transport properties [J].
Chen, ZJ ;
Debije, MG ;
Debaerdemaeker, T ;
Osswald, P ;
Würthner, F .
CHEMPHYSCHEM, 2004, 5 (01) :137-140
[4]  
Fernandez-Lazaro F., 2016, J MATER CHEM A, V4, P9336
[5]  
Frisch MJ, 2013, Gaussian 09
[6]   Detailed study of N,N′-(diisopropylphenyl)-terrylene-3,4:11,12-bis(dicarboximide) as electron acceptor for solar cells application [J].
Gorenflot, J. ;
Sperlich, A. ;
Baumann, A. ;
Rauh, D. ;
Vasilev, A. ;
Li, C. ;
Baumgarten, M. ;
Deibel, C. ;
Dyakonov, V. .
SYNTHETIC METALS, 2012, 161 (23-24) :2669-2676
[7]   Terrylenimides: New NIR fluorescent dyes [J].
Holtrup, FO ;
Muller, GRJ ;
Quante, H ;
Defeyter, S ;
DeSchryver, FC ;
Mullen, K .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (02) :219-225
[8]   Tailor-Made Rylene Arrays for High Performance n-Channel Semiconductors [J].
Jiang, Wei ;
Li, Yan ;
Wang, Zhaohui .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (10) :3135-3147
[9]   Bay-linked perylene bisimides as promising non-fullerene acceptors for organic solar cells [J].
Jiang, Wei ;
Ye, Long ;
Li, Xiangguang ;
Xiao, Chengyi ;
Tan, Fang ;
Zhao, Wenchao ;
Hou, Jianhui ;
Wang, Zhaohui .
CHEMICAL COMMUNICATIONS, 2014, 50 (08) :1024-1026
[10]   A new photostable terrylene diimide dye for applications in single molecule studies and membrane labeling [J].
Jung, C ;
Müller, BK ;
Lamb, DC ;
Nolde, F ;
Müllen, K ;
Bräuchle, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :5283-5291