Influence of heteroatoms on photovoltaic performance of donor-acceptor copolymers based on 2,6-di(thiophen-2-yl)benzo[1,2-b:4,5-b′]difurans and diketopyrrolopyrrole

被引:26
作者
Kobilka, Brandon M. [1 ]
Hale, Benjamin J. [1 ]
Ewan, Monique D. [1 ]
Dubrovskiy, Anton V. [1 ]
Nelson, Toby L. [2 ]
Duzhko, Volodimyr [3 ]
Jeffries-El, Malika [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
[2] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
[3] Univ Massachusetts, Dept Polymer Sci & Engn, Amherst, MA 01003 USA
基金
美国国家科学基金会;
关键词
POLYMER SOLAR-CELLS; FIELD-EFFECT TRANSISTORS; OPEN-CIRCUIT VOLTAGE; CONJUGATED POLYMERS; SEMICONDUCTING POLYMERS; ORGANIC PHOTOVOLTAICS; ALPHA-OLIGOFURANS; BANDGAP; EFFICIENCY; DESIGN;
D O I
10.1039/c3py00138e
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Donor-acceptor conjugated polymers based on the novel donor 3,7-didodecyl-2,6-di(thiophen-2-yl)benzo [1,2-b:4,5-b']difuran, and 1,4-diketopyrrolo[3,4-c]pyrrole as the acceptor were synthesized via the Stille cross-coupling reaction. The alkyl chains on the diketopyrrolopyrrole monomers were varied to engineer the solubility and morphology of the materials. Thiophene and furan moieties were used to flank the DPP group and the impact of these heterocycles on the polymers' properties evaluated. All of the polymers have similar optoelectronic properties with optical band-gaps of 1.3-1.4 eV, LUMO levels of -3.7 to -3.8 eV and HOMO levels of -5.5 to -5.6 eV. The furan-containing polymers have better solubility than the all-thiophene polymers, as significantly higher molecular weight materials of the former were readily dissolved. When the polymers were used as donor materials along with PC71BM as the electron-acceptor in bulk-heterojunction photovoltaic cells, power conversion efficiencies of up to 2.9% were obtained, with the furan-containing polymers giving the best results.
引用
收藏
页码:5329 / 5336
页数:8
相关论文
共 51 条
[1]   Spectral Engineering in π-Conjugated Polymers with Intramolecular Donor-Acceptor Interactions [J].
Beaujuge, Pierre M. ;
Amb, Chad M. ;
Reynolds, John R. .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (11) :1396-1407
[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]   Efficient Solar Cells Based on an Easily Accessible Diketopyrrolopyrrole Polymer [J].
Bijleveld, Johan C. ;
Gevaerts, Veronique S. ;
Di Nuzzo, Daniele ;
Turbiez, Mathieu ;
Mathijssen, Simon G. J. ;
de Leeuw, Dago M. ;
Wienk, Martijn M. ;
Janssen, Rene A. J. .
ADVANCED MATERIALS, 2010, 22 (35) :E242-+
[4]   High-mobility ambipolar near-infrared light-emitting polymer field-effect transistors [J].
Buergi, Lukas ;
Turbiez, Mathieu ;
Pfeiffer, Reto ;
Bienewald, Frank ;
Kirner, Hans-Joerg ;
Winnewisser, Carsten .
ADVANCED MATERIALS, 2008, 20 (11) :2217-2224
[5]   α-Oligofurans: Molecules without a Twist [J].
Bunz, Uwe H. F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (30) :5037-5040
[6]   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
[7]   Polymer solar cells with enhanced open-circuit voltage and efficiency [J].
Chen, Hsiang-Yu ;
Hou, Jianhui ;
Zhang, Shaoqing ;
Liang, Yongye ;
Yang, Guanwen ;
Yang, Yang ;
Yu, Luping ;
Wu, Yue ;
Li, Gang .
NATURE PHOTONICS, 2009, 3 (11) :649-653
[8]   A new benzo[1,2-b:4,5-b′]difuran-based copolymer for efficient polymer solar cells [J].
Chen, Xuewen ;
Liu, Bo ;
Zou, Yingping ;
Xiao, Lu ;
Guo, Xiuping ;
He, Yuehui ;
Li, Yongfang .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (34) :17724-17731
[10]   α-Oligofurans [J].
Gidron, Ori ;
Diskin-Posner, Yael ;
Bendikov, Michael .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (07) :2148-+