Fluorinated Head-to-Head Dialkoxybithiophene: A New Electron-Donating Building Block for High-Performance Polymer Semiconductors

Huang, Jun1,2,3; Guo, Han1,2; Uddin, Mohammad Afsar4; Yu, Jianwei1,2; Woo, Han Young4; Guo, Xugang1,2

2018-03

10.1002/aelm.201700519

Advanced Electronic Materials   影响因子和分区

2199-160X

New building blocks with good solubility and optimized optoelectrical property are critical for materials development in organic electronics. Herein, a new head-to-head linkage containing a donor unit, 4,4'-difluoro-3,3'-dialkoxy-2,2'-bithiophene (BTfOR), is synthesized. The dialkoxy chains afford good materials solubility and also planar backbone via noncovalent (thienyl) S.(alkoxy) O interactions. Compared to the reported 3,3'-dialkoxy-2,2'-bithiophene (BTOR), F addition leads to BTfOR with lower-lying frontier molecular orbitals and can further promote polymer packing via additional F ... S or F ... H interactions. BTfOR can be readily stannylated to afford tin monomer with high purity and excellent reactivity toward Stille polymerization. As a proof of concept for materials design, BTfOR-based homopolymer (PBTfOR) is synthesized, showing high molecular weight and strong aggregation. Moreover, the HOMO (-4.98 eV) of PBTfOR is greatly lower than that (-4.54 eV) of nonfluorinated counterpart PBTOR, which is attributed to the addition of F atoms. When incorporated into thin-film transistors, PBTfOR exhibits a remarkable hole mobility of 0.57 cm(2) V-1 s(-1), showing an exceptional example of high-mobility head-to-head polythiophene. This study demonstrates that introduction of F atoms can lead to BTfOR with optimized physicochemical properties, and the new BTfOR should find promising use for constructing donor-acceptor copolymers for high-performance electronic devices.

fluorinated thiophenes head-to-head linkages noncovalent sulfuroxygen interactions organic thin-film transistors polythiophenes

SCI

英语

第一 ; 通讯

NRF of Korea[2016M1A2A2940911] ; NRF of Korea[20100020209]

Science & Technology - Other Topics ; Materials Science ; Physics

Nanoscience & Nanotechnology ; Materials Science, Multidisciplinary ; Physics, Applied

WOS:000427002100009

WILEY

Web of Science

1.South Univ Sci & Technol China, Dept Mat Sci & Engn, 1088 Xueyuan Rd, Shenzhen 518055, Guangdong, Peoples R China
2.South Univ Sci & Technol China, Shenzhen Key Lab Printed Organ Elect, 1088 Xueyuan Rd, Shenzhen 518055, Guangdong, Peoples R China
3.Wuhan Univ, Dept Chem, Wuhan 430072, Hubei, Peoples R China
4.Korea Univ, Res Inst Nat Sci, Dept Chem, Seoul 136713, South Korea

Huang, Jun,Guo, Han,Uddin, Mohammad Afsar,et al. Fluorinated Head-to-Head Dialkoxybithiophene: A New Electron-Donating Building Block for High-Performance Polymer Semiconductors[J]. Advanced Electronic Materials,2018,4(3).

Huang, Jun,Guo, Han,Uddin, Mohammad Afsar,Yu, Jianwei,Woo, Han Young,&Guo, Xugang.(2018).Fluorinated Head-to-Head Dialkoxybithiophene: A New Electron-Donating Building Block for High-Performance Polymer Semiconductors.Advanced Electronic Materials,4(3).

Huang, Jun,et al."Fluorinated Head-to-Head Dialkoxybithiophene: A New Electron-Donating Building Block for High-Performance Polymer Semiconductors".Advanced Electronic Materials 4.3(2018).