Citation: Kai Guo, Yu Jiang, Ying Sui, Yun-Feng Deng, Yan-Hou Geng. Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers[J]. Chinese Journal of Polymer Science, ;2019, 37(11): 1099-1104. doi: 10.1007/s10118-019-2277-1 shu

Dimethylacetamide-promoted Direct Arylation Polycondensation of 6,6′-Dibromo-7,7′-diazaisoindigo and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene toward High Molecular Weight n-Type Conjugated Polymers

Kai Guo ^a ,
Yu Jiang ^b ,
Ying Sui ^a ,
Yun-Feng Deng ^a,, ,
Yan-Hou Geng ^a,c,,

a.
School of Materials Science and Engineering, Tianjin University, Tianjin 300072, China
b.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
c.
Tianjin Key Laboratory of Molecular Optoelectronic Science, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China

Corresponding author: Yun-Feng Deng, yunfeng.deng@tju.edu.cn Yan-Hou Geng, yanhou.geng@tju.edu.cn
Received Date: 11 March 2019
Revised Date: 15 April 2019
Available Online: 17 June 2019

A highly efficient and eco-friendly protocol for the synthesis of an alternating copolymer poly(7,7′-diazaisoindigo-alt-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene) (PAIID-4FTVT) via direct arylation polycondensation (DArP) is presented. Through detailed study, we found that the inhibitory effect of 7,7′-diazaisoindigo on DArP stemmed from the coordination of N atom with catalyst can be overcome by using dimethylacetamide (DMAc) as the co-solvent. Thus, PAIID-4FTVT with number-average molecular weight (M_n) > 100 kDa was synthesized via DArP by optimizing the content of DMAc. Matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectroscopy revealed that PAIID-4FTVT was defect-free. Top gate and bottom contact (TG/BC) organic thin-film transistors (OTFTs) were fabricated to characterize the semiconducting properties of the polymers. PAIID-4FTVT displayed unipolar n-type characteristics with the electron mobility (μ_e) strongly dependent on M_n. The highest μ_e up to 0.25 cm²·V^–1·s^–1 was achieved with the high molecular weight sample.
- Direct arylation polycondensation,
- Conjugated polymer,
- 7,7′-Diazaisoindigo,
- Organic thin-film transistor,
- Electron mobility
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