Electroactive and Photoactive Poly[lsoindigo-alt-EDOT] Synthesized Using Direct (Hetero)Arylation Polymerization in Batch and in Continuous Flow

被引:79
作者
Grenier, Francois [1 ]
Aich, Badrou Reda [1 ,2 ]
Lai, Yu-Ying [3 ]
Guerette, Maxime [1 ]
Holmes, Andrew B. [3 ]
Tao, Ye [2 ]
Wong, Wallace W. H. [3 ]
Leclerc, Mario [1 ]
机构
[1] Univ Laval, Dept Chim, Quebec City, PQ G1V 0A6, Canada
[2] Natl Res Council Canada, Informat & Commun Technol Portfolio, Ottawa, ON K1A 0R6, Canada
[3] Univ Melbourne, Sch Chem, Inst Bio21, Parkville, Vic 3010, Australia
基金
加拿大自然科学与工程研究理事会; 澳大利亚研究理事会;
关键词
DIRECT ARYLATION POLYMERIZATION; CONJUGATED POLYMERS; PHOTOVOLTAIC PROPERTIES; HOLE MOBILITIES; SOLAR-CELLS; BAND-GAP; POLYCONDENSATION; OLIGOMERS; EFFICIENT; PERFORMANCE;
D O I
10.1021/acs.chemmater.5b00083
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this work, a combined approach was used to obtain a low-cost material for organic electronics by focusing on inexpensive monomers, short synthetic pathway, high-yielding polymerization method, low waste, and easy scalability. To achieve this, a new material, poly[isoindigo-alt-3,4-ethylenedioxythiophene], was synthesized using direct (hetero)arylation polymerization (DHAP). Only a few synthetic steps are required to obtain this material, and no organometallic intermediates are used. In order to make a bigger step toward a truly inexpensive technology, continuous flow methods were applied for the first time to DHAP. This method helped solving a common problem encountered in conjugated polymers synthesis, namely, batch-to-batch variations. Electronic properties of this polymeric material were evaluated using field effect transistors (mu(h) = 7 x 10(-3) cm(2).V-1.s(-1)) and solar cells (eta = 3.0%).
引用
收藏
页码:2137 / 2143
页数:7
相关论文
共 61 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]   The Influence of Polymer Purification on Photovoltaic Device Performance of a Series of Indacenodithiophene Donor Polymers [J].
Ashraf, Raja Shahid ;
Schroeder, Bob C. ;
Bronstein, Hugo A. ;
Huang, Zhenggang ;
Thomas, Stuart ;
Kline, R. Joseph ;
Brabec, Christoph J. ;
Rannou, Patrice ;
Anthopoulos, Thomas D. ;
Durrant, James R. ;
McCulloch, Iain .
ADVANCED MATERIALS, 2013, 25 (14) :2029-2034
[3]   Palladium-catalysed direct polyheteroarylation of di- or tribromobenzene derivatives: a one step synthesis of conjugated poly(hetero)aromatics [J].
Baloch, Marya ;
Roy, Reny Jacob ;
Roy, David ;
Beydoun, Kassem ;
Doucet, Henri .
RSC ADVANCES, 2011, 1 (08) :1527-1536
[4]   Continuous Synthesis of Device-Grade Semiconducting Polymers in Droplet-Based Microreactors [J].
Bannock, James H. ;
Krishnadasan, Siva H. ;
Nightingale, Adrian M. ;
Yau, Chin Pang ;
Khaw, Kevin ;
Burkitt, Daniel ;
Halls, Jonathan J. M. ;
Heeney, Martin ;
de Mello, John C. .
ADVANCED FUNCTIONAL MATERIALS, 2013, 23 (17) :2123-2129
[5]   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
[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]   Cyclopentadithiophene-benzothiadiazole oligomers: Synthesis via direct arylation, X-ray crystallography, optical properties, solution casted field-effect transistor and photovoltaic characteristics [J].
Chang, Shu-Wei ;
Waters, Huw ;
Kettle, Jeff ;
Horie, Masaki .
ORGANIC ELECTRONICS, 2012, 13 (12) :2967-2974
[8]   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
[9]   Palladium-catalysed direct arylation of thiophenes tolerant to silyl groups [J].
Chen, Lu ;
Roger, Julien ;
Bruneau, Christian ;
Dixneuf, Pierre H. ;
Doucet, Henri .
CHEMICAL COMMUNICATIONS, 2011, 47 (06) :1872-1874
[10]   Microwave-Assisted Polycondensation via Direct Arylation of 3,4-Ethylenedioxythiophene with 9,9-Dioctyl-2,7-dibromofluorene [J].
Choi, Seong Jib ;
Kuwabara, Junpei ;
Kanbara, Takaki .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (08) :878-882