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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 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.

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 (NSFC)
OSTI Identifier:
1432056
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
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. https://doi.org/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. https://doi.org/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},
number = 7,
volume = 6,
place = {United States},
year = {Wed Jan 17 00:00:00 EST 2018},
month = {Wed Jan 17 00:00:00 EST 2018}
}

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Cited by: 10 works
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Figures / Tables:

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

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Works referencing / citing this record:

Vinylene spacer effects of benzothiadiazole–quarterthiophene based conjugated polymers on transistor mobilities
journal, January 2018

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