Drastic Effects of Fluorination on Backbone Conformation of Head-to-Head Bithiophene-Based Polymer Semiconductors

Qiaogan Liao, Yulun Wang, Mohammad Afsar Uddin, Jianhua Chen, Han Guo, Shengbin Shi, Yang Wang, Han Young Woo, Xugang Guo

    Research output: Contribution to journalArticlepeer-review

    24 Citations (Scopus)

    Abstract

    This study shows that the backbone conformation of head-to-head type 3,3′-dialkyl-2,2′-bithiophene can be tuned via fluorination of the neighboring benzothiadiazole (BTz). Without fluorination, the polymer backbone is highly twisted, whereas difluorination of BTz produced a coplanar backbone. Monofluorination of BTz yielded a tunable polymer backbone conformation depending on the film annealing temperature. In organic thin-film transistors, the polymer with the head-to-head linkages showed a remarkable hole mobility of >0.5 cm2 V-1 s-1 upon attaining a planar backbone. Thus, the head-to-head linkage does not necessarily lead to backbone nonplanarity, and achieving planar conformation of 3,3′-dialkyl-2,2′-bithiophene has profound implications in materials design for organic semiconducting devices, yielding good solubility, reduced materials synthetic steps, and improved opto-electrical properties.

    Original languageEnglish
    Pages (from-to)519-524
    Number of pages6
    JournalACS Macro Letters
    Volume7
    Issue number5
    DOIs
    Publication statusPublished - 2018 May 15

    Bibliographical note

    Funding Information:
    X.G. thanks NSFC (21774055 and 51573076), Shenzhen Peacock Plan (KQTD20140630110339343), Shenzhen Basic Research Fund (JCYJ20160530185244662), Shenzhen Key Lab funding (ZDSYS201505291525382), the Guangdong Natural Science Foundation (2015A030313900), and the South University of Science and Technology of China (FRG-SUSTC1501A-72). M.A.U. and H.Y.W. are grateful to the financial support from the NRF of Korea (2016M1A2A2940911 and 20100020209).

    Publisher Copyright:
    Copyright © 2018 American Chemical Society.

    ASJC Scopus subject areas

    • Organic Chemistry
    • Polymers and Plastics
    • Inorganic Chemistry
    • Materials Chemistry

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