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

被引:47
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
[1]   Novel oxadiazole side chain conjugated polymers as single-layer light-emitting diodes with improved quantum efficiencies [J].
Bao, ZA ;
Peng, ZH ;
Galvin, ME ;
Chandross, EA .
CHEMISTRY OF MATERIALS, 1998, 10 (05) :1201-1204
[2]   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
[3]  
Brabec CJ, 2001, ADV FUNCT MATER, V11, P15, DOI 10.1002/1616-3028(200102)11:1<15::AID-ADFM15>3.0.CO
[4]  
2-A
[5]   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
[6]   Triazatruxene-Diketopyrrolopyrrole Dumbbell-Shaped Molecules as Photoactive Electron Donor for High-Efficiency Solution Processed Organic Solar Cells [J].
Bura, Thomas ;
Leclerc, Nicolas ;
Bechara, Rony ;
Leveque, Patrick ;
Heiser, Thomas ;
Ziessel, Raymond .
ADVANCED ENERGY MATERIALS, 2013, 3 (09) :1118-1124
[7]   LIGHT-EMITTING-DIODES BASED ON CONJUGATED POLYMERS [J].
BURROUGHES, JH ;
BRADLEY, DDC ;
BROWN, AR ;
MARKS, RN ;
MACKAY, K ;
FRIEND, RH ;
BURN, PL ;
HOLMES, AB .
NATURE, 1990, 347 (6293) :539-541
[8]   Stille Polycondensation for Synthesis of Functional Materials [J].
Carsten, Bridget ;
He, Feng ;
Son, Hae Jung ;
Xu, Tao ;
Yu, Luping .
CHEMICAL REVIEWS, 2011, 111 (03) :1493-1528
[9]   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
[10]   Development of Novel Conjugated Donor Polymers for High-Efficiency Bulk-Heterojunction Photovoltaic Devices [J].
Chen, Junwu ;
Cao, Yong .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (11) :1709-1718