Accessing New DPP-Based Copolymers by Direct Heteroarylation Polymerization

被引:54
作者
Pouliot, Jean-Remi [1 ]
Mercier, Lauren G. [1 ]
Caron, Samuel [1 ]
Leclerc, Mario [1 ]
机构
[1] Univ Laval, Dept Chem, Quebec City, PQ G1V 0A6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
conjugated polymers; copolymerization; diketopyrrolopyrrole; direct heteroarylation; organic field-effect transistor; FIELD-EFFECT TRANSISTORS; CATALYZED DIRECT ARYLATION; HIGH-PERFORMANCE AMBIPOLAR; CONJUGATED POLYMERS; MOBILITY; ACCEPTOR; SEMICONDUCTORS; DESIGN; HOLE;
D O I
10.1002/macp.201200573
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A diketopyrrolopyrrole derivative was copolymerized with different electron-withdrawing units [i.e., thieno[3,4-c]pyrrole-4,6-dione (TPD), bis(thieno[3,4-c]pyrrole-4,6-dione) (BTPD), and 3,4-dicyanothiophene (DCT)] using direct heteroarylation polymerization (DHAP) methodology. Alternating copolymers with low-lying frontier orbitals suitable for n-type semiconducting behavior were obtained. Under optimized conditions, polymerization reactions were reproducible and high number-average molecular weights (Mn) were achieved. Density functional theory (DFT) calculations indicated that the structures with the lowest conformational energy had planar backbones. Preliminary results showed that these new low-bandgap materials exhibit good n-type behavior.
引用
收藏
页码:453 / 457
页数:5
相关论文
共 45 条
[1]   Easy and versatile synthesis of new poly(thieno[3,4-d]thiazole)s [J].
Allard, Nicolas ;
Najari, Ahmed ;
Pouliot, Jean-Remi ;
Pron, Agnieszka ;
Grenier, Francois ;
Leclerc, Mario .
POLYMER CHEMISTRY, 2012, 3 (10) :2875-2879
[2]   Air-stable ambipolar organic transistors [J].
Anthopoulos, Thomas D. ;
Anyfantis, G. C. ;
Papavassiliou, G. C. ;
de Leeuw, Dago M. .
APPLIED PHYSICS LETTERS, 2007, 90 (12)
[3]   Synthesis of 5-Alkyl[3,4-c]thienopyrrole-4,6-dione-Based Polymers by Direct Heteroarylation [J].
Berrouard, Philippe ;
Najari, Ahmed ;
Pron, Agnieszka ;
Gendron, David ;
Morin, Pierre-Olivier ;
Pouliot, Jean-Remi ;
Veilleux, Justine ;
Leclerc, Mario .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) :2068-2071
[4]   Synthesis and Characterization of 5-Octylthieno[3,4-c]pyrrole-4,6-dione Derivatives As New Monomers for Conjugated Copolymers [J].
Berrouard, Philippe ;
Grenier, Francois ;
Pouliot, Jean-Remi ;
Gagnon, Eric ;
Tessier, Christian ;
Leclerc, Mario .
ORGANIC LETTERS, 2011, 13 (01) :38-41
[5]   Pd-Catalysed Direct Arylation Polymerisation for Synthesis of Low-Bandgap Conjugated Polymers and Photovoltaic Performance [J].
Chang, Shu-Wei ;
Waters, Huw ;
Kettle, Jeff ;
Kuo, Zi-Rui ;
Li, Chun-Han ;
Yu, Chin-Yang ;
Horie, Masaki .
MACROMOLECULAR RAPID COMMUNICATIONS, 2012, 33 (22) :1927-1932
[6]   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
[7]   Recent Developments in Top-Emitting Organic Light-Emitting Diodes [J].
Chen, Shufen ;
Deng, Lingling ;
Xie, Jun ;
Peng, Ling ;
Xie, Linghai ;
Fan, Quli ;
Huang, Wei .
ADVANCED MATERIALS, 2010, 22 (46) :5227-5239
[8]   High-Performance Ambipolar Diketopyrrolopyrrole-Thieno[3,2-b]thiophene Copolymer Field-Effect Transistors with Balanced Hole and Electron Mobilities [J].
Chen, Zhuoying ;
Lee, Mi Jung ;
Ashraf, Raja Shahid ;
Gu, Yun ;
Albert-Seifried, Sebastian ;
Nielsen, Martin Meedom ;
Schroeder, Bob ;
Anthopoulos, Thomas D. ;
Heeney, Martin ;
McCulloch, Iain ;
Sirringhaus, Henning .
ADVANCED MATERIALS, 2012, 24 (05) :647-+
[9]   Effects of the Molecular Weight and the Side-Chain Length on the Photovoltaic Performance of Dithienosilole/Thienopyrrolodione Copolymers [J].
Chu, Ta-Ya ;
Lu, Jianping ;
Beaupre, Serge ;
Zhang, Yanguang ;
Pouliot, Jean-Remi ;
Zhou, Jiayun ;
Najari, Ahmed ;
Leclerc, Mario ;
Tao, Ye .
ADVANCED FUNCTIONAL MATERIALS, 2012, 22 (11) :2345-2351
[10]   Bulk Heterojunction Solar Cells Using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole Copolymer with a Power Conversion Efficiency of 7.3% [J].
Chu, Ta-Ya ;
Lu, Jianping ;
Beaupre, Serge ;
Zhang, Yanguang ;
Pouliot, Jean-Remi ;
Wakim, Salem ;
Zhou, Jiayun ;
Leclerc, Mario ;
Li, Zhao ;
Ding, Jianfu ;
Tao, Ye .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4250-4253