Rational design of π-bridges for ambipolar DPP-RH-based small molecules in organic photovoltaic cells

被引:21
作者
Eom, Yoonho [1 ]
Song, Chang Eun [2 ]
Shin, Won Suk [2 ]
Lee, Sang Kyu [2 ]
Lim, Eunhee [1 ]
机构
[1] Kyonggi Univ, Dept Chem, San 94-6, Suwon 443760, Gyeonggi, South Korea
[2] KRICT, 100 Jang Dong, Daejeon 305600, South Korea
基金
新加坡国家研究基金会;
关键词
Organic photovoltaic cell (OPV); Organic solar cell; Diketopyrrolopyrrole (DPP); Thiophene; Acceptor; POLYMER SOLAR-CELLS; POWER CONVERSION EFFICIENCY; BAND-GAP POLYMER; 11-PERCENT EFFICIENCY; ELECTRON-ACCEPTORS; PERFORMANCE; DIKETOPYRROLOPYRROLE; FULLERENE; BENZOTHIADIAZOLE; OLIGOTHIOPHENES;
D O I
10.1016/j.jiec.2016.10.001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the synthesis of a series of A1-pi-A2-pi-A1-type small molecules, DPP2T-RH, DPPFT-RH, and DPPT-RH, in which thiophene and furan were introduced to bridge the two strong electron-withdrawing units of DPP and rhodanine (RH). Interestingly, these DPP-RH-based small molecules exhibited ambipolar characteristics, showing photovoltaic performance both as donors and acceptors in combination with PC71BM and P3HT, respectively. The best power conversion efficiencies were obtained from DPPFT-RH (1.77%) and DPP2T-RH (1.28%) as donor and acceptor, respectively. Their physical properties, film packing ability, and photovoltaic performances were fine-tuned by rational design of pi-bridges. (C) 2016 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:338 / 348
页数:11
相关论文
共 48 条
[1]   A high-performance ambipolar organic field-effect transistor based on a bidirectional π-extended diketopyrrolopyrrole under ambient conditions [J].
Bai, Jinfeng ;
Liu, Yucun ;
Oh, Sangyoon ;
Lei, Wenwei ;
Yin, Bingzhu ;
Park, Sooyoung ;
Kan, Yuhe .
RSC ADVANCES, 2015, 5 (66) :53412-53418
[2]   Small band gap copolymers based on furan and diketopyrrolopyrrole for field-effect transistors and photovoltaic cells [J].
Bijleveld, Johan C. ;
Karsten, Bram P. ;
Mathijssen, Simon G. J. ;
Wienk, Martijn M. ;
de Leeuw, Dago M. ;
Janssen, Rene A. J. .
JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (05) :1600-1606
[3]   Synthesis and Characterization of Optical and Redox Properties of Bithiophene-Functionalized Diketopyrrolopyrrole Chromophores [J].
Buerckstuemmer, Hannah ;
Weissenstein, Annike ;
Bialas, David ;
Wuerthner, Frank .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2426-2432
[4]   Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications [J].
Cardona, Claudia M. ;
Li, Wei ;
Kaifer, Angel E. ;
Stockdale, David ;
Bazan, Guillermo C. .
ADVANCED MATERIALS, 2011, 23 (20) :2367-2371
[5]   Synthesis and characterization of triphenylamine flanked thiazole-based small molecules for high performance solution processed organic solar cells [J].
Dutta, Pranabesh ;
Yang, Wooseung ;
Eom, Seung Hun ;
Lee, Soo-Hyoung .
ORGANIC ELECTRONICS, 2012, 13 (02) :273-282
[6]   Deep Absorbing Porphyrin Small Molecule for High-Performance Organic Solar Cells with Very Low Energy Losses [J].
Gao, Ke ;
Li, Lisheng ;
Lai, Tianqi ;
Xiao, Liangang ;
Huang, Yuan ;
Huang, Fei ;
Peng, Junbiao ;
Cao, Yong ;
Liu, Feng ;
Russell, Thomas P. ;
Janssen, Rene A. J. ;
Peng, Xiaobin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (23) :7282-7285
[7]   Bandgap and Molecular Level Control of the Low-Bandgap Polymers Based on 3,6-Dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione toward Highly Efficient Polymer Solar Cells [J].
Huo, Lijun ;
Hou, Jianhui ;
Chen, Hsing-Yu ;
Zhang, Shaoqing ;
Jiang, Yang ;
Chen, Teresa L. ;
Yang, Yang .
MACROMOLECULES, 2009, 42 (17) :6564-6571
[8]   Low-Bandgap Small Molecules as Non-Fullerene Electron Acceptors Composed of Benzothiadiazole and Diketopyrrolopyrrole for All Organic Solar Cells [J].
Jung, Jae Woong ;
Jo, Won Ho .
CHEMISTRY OF MATERIALS, 2015, 27 (17) :6038-6043
[9]   A Small Molecule Composed of Dithienopyran and Diketopyrrolopyrrole as Versatile Electron Donor Compatible with Both Fullerene and Nonfullerene Electron Acceptors for High Performance Organic Solar Cells [J].
Jung, Jae Woong ;
Russell, Thomas P. ;
Jo, Won Ho .
CHEMISTRY OF MATERIALS, 2015, 27 (13) :4865-4870
[10]   Highly Crystalline Low Band Gap Polymer Based on Thieno[3,4-c]pyrrole-4,6-dione for High-Performance Polymer Solar Cells with a >400 nm Thick Active Layer [J].
Jung, Jae Woong ;
Russell, Thomas P. ;
Jo, Won Ho .
ACS APPLIED MATERIALS & INTERFACES, 2015, 7 (24) :13666-13674