Semiconducting Polymers Based on Simple Electron-Deficient Cyanated trans-1,3-Butadienes for Organic Field-Effect Transistors

Li，Jianfeng1; Chen，Zhicai1,2; Wang，Junwei1; Young Jeong，Sang3; Yang，Kun4; Feng，Kui1; Yang，Jie1; Liu，Bin1; Woo，Han Young3; Guo，Xugang1,5

2023-09-18

10.1002/anie.202307647

Angewandte Chemie - International Edition   Impact Factor & Quartile

1433-7851

1521-3773

Developing high-performance but low-cost n-type polymers remains a significant challenge in the commercialization of organic field-effect transistors (OFETs). To achieve this objective, it is essential to design the key electron-deficient units with simple structures and facile preparation processes, which can facilitate the production of low-cost n-type polymers. Herein, by sequentially introducing fluorine and cyano functionalities onto trans-1,3-butadiene, we developed a series of structurally simple but highly electron-deficient building blocks, namely 1,4-dicyano-butadiene (CNDE), 3-fluoro-1,4-dicyano-butadiene (CNFDE), and 2,3-difluoro-1,4-dicyano-butadiene (CNDFDE), featuring a highly coplanar backbone and deep-positioned lowest unoccupied molecular orbital (LUMO) energy levels (−3.03–4.33 eV), which render them highly attractive for developing n-type semiconducting polymers. Notably, all these electron-deficient units can be easily accessed by a two-step high-yield synthetic procedure from low-cost raw materials, thus rendering them highly promising candidates for commercial applications. Upon polymerization with diketopyrrolopyrrole (DPP), three copolymers were developed that demonstrated unipolar n-type transport characteristics in OFETs with the highest electron mobility of >1 cm V s. Hence, CNDE, CNFDE, and CNDFDE represent a class of novel, simple, and efficient electron-deficient units for constructing low-cost n-type polymers, thereby providing valuable insight for OFET applications.

Cyano-Functionalized Polymers Electron Acceptors Organic Thin-Film Transistors Semiconducting Polymers

SCI

English

NI Journal Papers

First ; Corresponding

National Research Foundation of Korea[2019R1A6A1A11044070];Basic and Applied Basic Research Foundation of Guangdong Province[2022A1515110635];Basic and Applied Basic Research Foundation of Guangdong Province[2023A1515012607];National Natural Science Foundation of China[22105096];National Natural Science Foundation of China[52173171];

Chemistry

Chemistry, Multidisciplinary

WOS:001044593600001

WILEY-V C H VERLAG GMBH

CHEMISTRY

2-s2.0-85167343611

Scopus

1.Department of Materials Science and Engineering,Southern University of Science and Technology (SUSTech),Shenzhen,Guangdong,518055,China
2.Department State Key Laboratory of Marine Resource Utilization in South China Sea,College of Materials Science and Engineering,Hainan University,Haikou,Hainan,570228,China
3.Research Institute for Natural Sciences,Department of Chemistry,Korea University,Seoul,02841,South Korea
4.State Key Laboratory of Chemo/Biosensing and Chemometrics,College of Chemistry and Chemical Engineering,Hunan University,Changsha,Hunan,410082,China
5.Songshan Lake Materials Laboratory,Dongguan,Guangdong,523808,China

Li，Jianfeng,Chen，Zhicai,Wang，Junwei,et al. Semiconducting Polymers Based on Simple Electron-Deficient Cyanated trans-1,3-Butadienes for Organic Field-Effect Transistors[J]. Angewandte Chemie - International Edition,2023,62(38).

Li，Jianfeng.,Chen，Zhicai.,Wang，Junwei.,Young Jeong，Sang.,Yang，Kun.,...&Guo，Xugang.(2023).Semiconducting Polymers Based on Simple Electron-Deficient Cyanated trans-1,3-Butadienes for Organic Field-Effect Transistors.Angewandte Chemie - International Edition,62(38).

Li，Jianfeng,et al."Semiconducting Polymers Based on Simple Electron-Deficient Cyanated trans-1,3-Butadienes for Organic Field-Effect Transistors".Angewandte Chemie - International Edition 62.38(2023).