Balanced Ambipolar Poly(diketopyrrolopyrrole-alt-tetrafluorobenzene) Semiconducting Polymers Synthesized via Direct Arylation Polymerization

被引:48
作者
Wang, Kai [1 ]
Wang, Guojie [1 ]
Wang, Mingfeng [1 ]
机构
[1] Nanyang Technol Univ, Sch Chem & Biomed Engn, Div Chem & Biomol Engn, Singapore 637457, Singapore
关键词
diketopyrrolopyrroles; direct arylation polymerization; OFETs; semiconducting polymers; CROSS-COUPLING REACTIONS; LIGHT-EMITTING-DIODES; CONJUGATED POLYMERS; SOLAR-CELLS; HIGH HOLE; EFFICIENT APPROACH; BANDGAP; MOBILITY; POLYCONDENSATION; (HETERO)ARYLATION;
D O I
10.1002/marc.201500377
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The synthesis of an ambipolar pi-conjugated copolymer consisting of alternating diketopyrrolopyrrole and tetrafluorobenzene via direct arylation polymerization (DAP) is reported. Two different combinations of monomers are investigated under various catalytic conditions for DAP. The target polymer obtained under an optimized catalytic condition shows minimal structural defects, a number-average molecular weight of 33.2 kDa, and balanced electron and hole mobility of 1 x 10(-2) cm 2 V-1 S-1 in the organic field-effect transistors fabricated and tested under ambient conditions.
引用
收藏
页码:2162 / 2170
页数:9
相关论文
共 64 条
[31]   Polycondensation of Dibromofluorene Analogues with Tetrafluorobenzene via Direct Arylation [J].
Lu, Wei ;
Kuwabara, Junpei ;
Kanbara, Takaki .
MACROMOLECULES, 2011, 44 (06) :1252-1255
[32]   High-efficiency white-light emission from a single copolymer: Fluorescent blue, green, and red chromophores on a conjugated polymer backbone [J].
Luo, Jie ;
Li, Xianzhen ;
Hou, Qiong ;
Peng, Junbiao ;
Yang, Wei ;
Cao, Yong .
ADVANCED MATERIALS, 2007, 19 (08) :1113-1117
[33]   Direct (Hetero)Arylation: A New Tool for Polymer Chemists [J].
Mercier, Lauren G. ;
Leclerc, Mario .
ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (07) :1597-1605
[34]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[35]   Emeraldicene as an Acceptor Moiety: Balanced-Mobility, Ambipolar, Organic Thin-Film Transistors [J].
Mohebbi, Ali Reza ;
Yuen, Jonathan ;
Fan, Jian ;
Munoz, Cedric ;
Wang, Ming Feng ;
Shirazi, Rahau S. ;
Seifter, Jason ;
Wudl, Fred .
ADVANCED MATERIALS, 2011, 23 (40) :4644-+
[36]   Palladium-catalyzed Direct Arylation Approach to Synthesize Naphthalene Bisimide-based Low-band-gap Polymers [J].
Nakabayashi, Kazuhiro ;
Mori, Hideharu .
CHEMISTRY LETTERS, 2013, 42 (07) :717-718
[37]   Recent Advances in the Development of Semiconducting DPP-Containing Polymers for Transistor Applications [J].
Nielsen, Christian B. ;
Turbiez, Mathieu ;
McCulloch, Iain .
ADVANCED MATERIALS, 2013, 25 (13) :1859-1880
[38]   C-H Arylation Reaction: Atom Efficient and Greener Syntheses of π-Conjugated Small Molecules and Macromolecules for Organic Electronic Materials [J].
Okamoto, Ken ;
Zhang, Junxiang ;
Housekeeper, Jeremy B. ;
Marder, Seth R. ;
Luscombe, Christine K. .
MACROMOLECULES, 2013, 46 (20) :8059-8078
[39]   A Fluorinated Phenylene Unit as a Building Block for High-Performance n-Type Semiconducting Polymer [J].
Park, Jung Ha ;
Jung, Eui Hyuk ;
Jung, Jae Woong ;
Jo, Won Ho .
ADVANCED MATERIALS, 2013, 25 (18) :2583-2588
[40]   Efficiency enhancement in low-bandgap polymer solar cells by processing with alkane dithiols [J].
Peet, J. ;
Kim, J. Y. ;
Coates, N. E. ;
Ma, W. L. ;
Moses, D. ;
Heeger, A. J. ;
Bazan, G. C. .
NATURE MATERIALS, 2007, 6 (07) :497-500