Direct Arylation Polymerization for Synthesizing a Library of Conjugated Porous Polymers Containing Thiophene-Flanked Building Blocks

被引:18
作者
Bohra, Hassan [1 ]
Wang, Mingfeng [1 ]
机构
[1] Nanyang Technol Univ, Sch Chem & Biomed Engn, 62 Nanyang Dr, Singapore 637459, Singapore
来源
ACS APPLIED POLYMER MATERIALS | 2019年 / 1卷 / 07期
关键词
polymer; porous materials; synthesis; direct arylation; thiophene; benzothiadiazole; diketopyrrolopyrrole; MICROPOROUS POLYMERS; DIKETOPYRROLOPYRROLE; BANDGAP; FACILE; POLYCONDENSATION; DERIVATIVES; POROSITY;
D O I
10.1021/acsapm.9b00271
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
Thiophene-flanked pi-conjugated building blocks are often used in the design of linear conjugated polymers as they leverage the reactivity of thiophene in numerous C-C coupling reactions to include a variety of donor and acceptor molecules in the conjugated backbone. However, this design strategy has been rarely used for synthesis of conjugated porous polymers (CPPs) until recently. In this article, we report facile synthesis and characterization of a library of CPPs synthesized via a versatile synthetic scheme of C-H direct arylation polymerization that involves commercially available aryl bromides and thiophene-flanked arenes. This synthetic scheme not only is atomically efficient compared to conventional couplings such as Suzuki, Stille, and Sonogashira coupling but also broadens the scope of building blocks to enable fine control of chemical structures, optoelectronic properties, and porosities that are important for applications such as photocatalysis.
引用
收藏
页码:1697 / 1706
页数:19
相关论文
共 51 条
[1]   A diketopyrrolopyrrole-based fluorescent porous organic polymer as fluoride sensing monolithic device [J].
Bi, Shiming ;
Li, Yankai ;
Zhang, Shaoze ;
Hu, Jun ;
Wang, Limin ;
Liu, Honglai .
JOURNAL OF MATERIALS CHEMISTRY C, 2018, 6 (15) :3961-3967
[2]   "Greener" and modular synthesis of triazine-based conjugated porous polymers via direct arylation polymerization: structure-function relationship and photocatalytic application [J].
Bohra, Hassan ;
Li, Peizhou ;
Yang, Cangjie ;
Zhao, Yanli ;
Wang, Mingfeng .
POLYMER CHEMISTRY, 2018, 9 (15) :1972-1982
[3]   Direct C-H arylation: a "Greener" approach towards facile synthesis of organic semiconducting molecules and polymers [J].
Bohra, Hassan ;
Wang, Mingfeng .
JOURNAL OF MATERIALS CHEMISTRY A, 2017, 5 (23) :11550-11571
[4]   Narrow bandgap thienothiadiazole-based conjugated porous polymers: from facile direct arylation polymerization to tunable porosities and optoelectronic properties [J].
Bohra, Hassan ;
Tan, Si Yu ;
Shao, Jinjun ;
Yang, Cangjie ;
Efrem, Amsalu ;
Zhao, Yanli ;
Wang, Mingfeng .
POLYMER CHEMISTRY, 2016, 7 (41) :6413-6421
[5]   Facile synthesis of naphthodithiophenediimide based small molecules and polymers via direct arylation coupling [J].
Bohra, Hassan ;
Shao, Jinjun ;
Huang, Shuo ;
Wang, Mingfeng .
TETRAHEDRON LETTERS, 2016, 57 (13) :1497-1501
[6]   Tuning Photophysical Properties in Conjugated Microporous Polymers by Comonomer Doping Strategies [J].
Bonillo, Baltasar ;
Sprick, Reiner Sebastian ;
Cooper, Andrew I. .
CHEMISTRY OF MATERIALS, 2016, 28 (10) :3469-3480
[7]   Diketopyrrolopyrrole: A versatile building block for organic photovoltaic materials [J].
Chandran, Deepak ;
Lee, Kwang-Sup .
MACROMOLECULAR RESEARCH, 2013, 21 (03) :272-283
[8]   Direct arylation polymerization towards narrow bandgap conjugated microporous polymers with hierarchical porosity [J].
Efrem, Amsalu ;
Wang, Kai ;
Amaniampong, Prince N. ;
Yang, Cangjie ;
Gupta, Sukriti ;
Bohra, Hassan ;
Mushrif, Samir H. ;
Wang, Mingfeng .
POLYMER CHEMISTRY, 2016, 7 (30) :4862-4866
[9]   Direct arylation polymerization: A guide to optimal conditions for effective conjugated polymers [J].
Gobalasingham, Nemal S. ;
Thompson, Barry C. .
PROGRESS IN POLYMER SCIENCE, 2018, 83 :135-201
[10]   Designing π-conjugated polymers for organic electronics [J].
Guo, Xin ;
Baumgarten, Martin ;
Muellen, Klaus .
PROGRESS IN POLYMER SCIENCE, 2013, 38 (12) :1832-1908