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Title: A vinyl flanked difluorobenzothiadiazole–dithiophene conjugated polymer for high performance organic field-effect transistors

Abstract

Fluorine containing conjugated polymers have been widely applied in high performance organic solar cells, but their use in field-effect transistors is still quite limited. In this work, a conjugated polymer PTFBTV based on difluorobenzothiadiazole (DFBT) and dithiophene was synthesized, utilizing multiple vinylene as linkers. The polymer exhibits a relatively high hole mobility up to 2.0 cm 2 V -1 s -1 compared with the reported DFBT–oligothiophene based polymers, yet its structural complexity is much simpler. The polymer thin film exhibits a typical ‘face on’ molecular orientation. A single crystal of its monomer revealed a non-covalent intramolecular contact between fluorine and the neighbouring proton, which strengthens the backbone co-planarity. Meanwhile an intermolecular F∙∙∙F contact was also observed, which might cause rather scattered lamellar crystallinity for PTFBTV in the solid state.

Authors:
 [1];  [2];  [2]; ORCiD logo [2];  [3]; ORCiD logo [3];  [4];  [5]; ORCiD logo [6];  [2]
  1. Chongqing Univ., Chongqing (China). School of Chemistry and Chemical Engineering; Yunnan Minzu Univ., Kunming (China). YMU-HKBU Joint Lab. of Traditional Natural Medicine
  2. Chongqing Univ., Chongqing (China). School of Chemistry and Chemical Engineering
  3. Chinese Academy of Sciences (CAS), Beijing (China). Beijing National Lab. for Molecular Sciences, Inst. of Chemistry
  4. Yunnan Minzu Univ., Kunming (China). YMU-HKBU Joint Lab. of Traditional Natural Medicine
  5. Chinese Academy of Sciences (CAS), Chongqing (China). Chongqing Inst. of Green and Intelligent Technology
  6. Argonne National Lab. (ANL), Argonne, IL (United States). Materials Science Division; Univ. of Chicago, IL (United States). Inst. for Molecular Engineering
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division; National Natural Science Foundation of China (NNSFC)
OSTI Identifier:
1432056
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Journal of Materials Chemistry C
Additional Journal Information:
Journal Volume: 6; Journal Issue: 7; Journal ID: ISSN 2050-7526
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Liang, Xianfeng, Sun, Wandong, Chen, Yanlin, Tan, Luxi, Cai, Zhengxu, Liu, Zitong, Wang, Lin, Li, Jing, Chen, Wei, and Dong, Lichun. A vinyl flanked difluorobenzothiadiazole–dithiophene conjugated polymer for high performance organic field-effect transistors. United States: N. p., 2018. Web. doi:10.1039/c7tc05360f.
Liang, Xianfeng, Sun, Wandong, Chen, Yanlin, Tan, Luxi, Cai, Zhengxu, Liu, Zitong, Wang, Lin, Li, Jing, Chen, Wei, & Dong, Lichun. A vinyl flanked difluorobenzothiadiazole–dithiophene conjugated polymer for high performance organic field-effect transistors. United States. doi:10.1039/c7tc05360f.
Liang, Xianfeng, Sun, Wandong, Chen, Yanlin, Tan, Luxi, Cai, Zhengxu, Liu, Zitong, Wang, Lin, Li, Jing, Chen, Wei, and Dong, Lichun. Wed . "A vinyl flanked difluorobenzothiadiazole–dithiophene conjugated polymer for high performance organic field-effect transistors". United States. doi:10.1039/c7tc05360f. https://www.osti.gov/servlets/purl/1432056.
@article{osti_1432056,
title = {A vinyl flanked difluorobenzothiadiazole–dithiophene conjugated polymer for high performance organic field-effect transistors},
author = {Liang, Xianfeng and Sun, Wandong and Chen, Yanlin and Tan, Luxi and Cai, Zhengxu and Liu, Zitong and Wang, Lin and Li, Jing and Chen, Wei and Dong, Lichun},
abstractNote = {Fluorine containing conjugated polymers have been widely applied in high performance organic solar cells, but their use in field-effect transistors is still quite limited. In this work, a conjugated polymer PTFBTV based on difluorobenzothiadiazole (DFBT) and dithiophene was synthesized, utilizing multiple vinylene as linkers. The polymer exhibits a relatively high hole mobility up to 2.0 cm2 V-1 s-1 compared with the reported DFBT–oligothiophene based polymers, yet its structural complexity is much simpler. The polymer thin film exhibits a typical ‘face on’ molecular orientation. A single crystal of its monomer revealed a non-covalent intramolecular contact between fluorine and the neighbouring proton, which strengthens the backbone co-planarity. Meanwhile an intermolecular F∙∙∙F contact was also observed, which might cause rather scattered lamellar crystallinity for PTFBTV in the solid state.},
doi = {10.1039/c7tc05360f},
journal = {Journal of Materials Chemistry C},
issn = {2050-7526},
number = 7,
volume = 6,
place = {United States},
year = {2018},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Figures / Tables:

Fig. 1 Fig. 1: Chemical structures and hole mobility of the DFBT–oligothiophene based conjugated polymers.

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Works referenced in this record:

A high-mobility electron-transporting polymer for printed transistors
journal, January 2009

  • Yan, He; Chen, Zhihua; Zheng, Yan
  • Nature, Vol. 457, Issue 7230, p. 679-686
  • DOI: 10.1038/nature07727

Polymer solar cells with enhanced open-circuit voltage and efficiency
journal, November 2009

  • Chen, Hsiang-Yu; Hou, Jianhui; Zhang, Shaoqing
  • Nature Photonics, Vol. 3, Issue 11, p. 649-653
  • DOI: 10.1038/nphoton.2009.192

    Works referencing / citing this record:

    CCDC 1516212: Experimental Crystal Structure Determination: YEWLOE : 4,7-bis(2-(5-bromo-4-butyl-2-thienyl)vinyl)-2,1,3-benzothiadiazole
    dataset, November 2016


      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.