Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents
This article describes the synthesis of donor–acceptor (D–A) type copolymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct-arylation cross-coupling polycondensation. To achieve high performance polymerization, we have systematically investigated the reaction factors i...
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| Format: | Journal Article |
| Language: | English |
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2014
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| Online Access: | https://hdl.handle.net/10356/103451 http://hdl.handle.net/10220/24513 |
| _version_ | 1826119188693909504 |
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| author | Wang, Xiaochen Wang, Mingfeng |
| author2 | School of Chemical and Biomedical Engineering |
| author_facet | School of Chemical and Biomedical Engineering Wang, Xiaochen Wang, Mingfeng |
| author_sort | Wang, Xiaochen |
| collection | NTU |
| description | This article describes the synthesis of donor–acceptor (D–A) type copolymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct-arylation cross-coupling polycondensation. To achieve high performance polymerization, we have systematically investigated the reaction factors including catalysts, solvents, ligands, bases, additives, concentration of reactants and phase transfer agents. In particular, 1,2-dimethylbenzene (ODMB), as a nonpolar high boiling point solvent, is a superior medium to perform this direct-arylation polymerization. In this nonpolar aromatic solvent, Pd2dba3/(o-MeOPh)3P, accompanied with a base potassium carbonate and an additive pivalic acid, serves as an efficient catalyst system to obtain high-quality polymers. Our optimized condition gave the polymer with a weight-average molecular weight (Mw) as high as 60 kg mol−1 in nearly quantitative yield and excellent C–H selectivity. |
| first_indexed | 2024-10-01T04:56:04Z |
| format | Journal Article |
| id | ntu-10356/103451 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:56:04Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1034512023-12-29T06:48:28Z Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents Wang, Xiaochen Wang, Mingfeng School of Chemical and Biomedical Engineering DRNTU::Science::Chemistry::Organic chemistry::Polymers This article describes the synthesis of donor–acceptor (D–A) type copolymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct-arylation cross-coupling polycondensation. To achieve high performance polymerization, we have systematically investigated the reaction factors including catalysts, solvents, ligands, bases, additives, concentration of reactants and phase transfer agents. In particular, 1,2-dimethylbenzene (ODMB), as a nonpolar high boiling point solvent, is a superior medium to perform this direct-arylation polymerization. In this nonpolar aromatic solvent, Pd2dba3/(o-MeOPh)3P, accompanied with a base potassium carbonate and an additive pivalic acid, serves as an efficient catalyst system to obtain high-quality polymers. Our optimized condition gave the polymer with a weight-average molecular weight (Mw) as high as 60 kg mol−1 in nearly quantitative yield and excellent C–H selectivity. Published version 2014-12-22T04:29:26Z 2019-12-06T21:12:58Z 2014-12-22T04:29:26Z 2019-12-06T21:12:58Z 2014 2014 Journal Article Wang, X., & Wang, M. (2014). Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents. Polymer chemistry, 5(19), 5784-5792. https://hdl.handle.net/10356/103451 http://hdl.handle.net/10220/24513 10.1039/C4PY00565A en Polymer chemistry This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. 9 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Polymers Wang, Xiaochen Wang, Mingfeng Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents |
| title | Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents |
| title_full | Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents |
| title_fullStr | Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents |
| title_full_unstemmed | Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents |
| title_short | Synthesis of donor-acceptor conjugated polymers based on benzo[1,2-b:4,5-b′]dithiophene and 2,1,3-benzothiadiazole via direct arylation polycondensation : towards efficient C-H activation in nonpolar solvents |
| title_sort | synthesis of donor acceptor conjugated polymers based on benzo 1 2 b 4 5 b dithiophene and 2 1 3 benzothiadiazole via direct arylation polycondensation towards efficient c h activation in nonpolar solvents |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Polymers |
| url | https://hdl.handle.net/10356/103451 http://hdl.handle.net/10220/24513 |
| work_keys_str_mv | AT wangxiaochen synthesisofdonoracceptorconjugatedpolymersbasedonbenzo12b45bdithiopheneand213benzothiadiazoleviadirectarylationpolycondensationtowardsefficientchactivationinnonpolarsolvents AT wangmingfeng synthesisofdonoracceptorconjugatedpolymersbasedonbenzo12b45bdithiopheneand213benzothiadiazoleviadirectarylationpolycondensationtowardsefficientchactivationinnonpolarsolvents |