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

Jun Huang, Han Guo, Mohammad Afsar Uddin, Jianwei Yu, Han Young Woo, Xugang Guo

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)


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 cm2 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.

Original languageEnglish
Article number1700519
JournalAdvanced Electronic Materials
Issue number3
Publication statusPublished - 2018 Mar

Bibliographical note

Funding Information:
J.H. and H.G. contributed equally to this work. X.G. thanks the National Science Foundation of China (21774055), Shenzhen Peacock Plan (KQTD20140630110339343), Shenzhen Basic Research Fund (JCYJ20160530185244662), Shenzhen Key Lab funding (ZDSYS201505291525382), the Guangdong Natural Science Foundation (2015A030313900), and South University of Science and Technology of China (FRG-SUSTC1501A-72). H.G. is grateful to Shenzhen Basic Research Fund (JCYJ20160530190226226). M.A.U. and H.Y.W. are grateful to the financial support from the NRF of Korea (2016M1A2A2940911, 20100020209).

Publisher Copyright:
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim


  • fluorinated thiophenes
  • head-to-head linkages
  • noncovalent sulfur⋯oxygen interactions
  • organic thin-film transistors
  • polythiophenes

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials


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