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

doi:10.1021/acsmacrolett.8b00032

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 journal › Article › peer-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 language	English
Pages (from-to)	519-524
Number of pages	6
Journal	ACS Macro Letters
Volume	7
Issue number	5
DOIs	https://doi.org/10.1021/acsmacrolett.8b00032
Publication status	Published - 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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10.1021/acsmacrolett.8b00032

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title = "Drastic Effects of Fluorination on Backbone Conformation of Head-to-Head Bithiophene-Based Polymer Semiconductors",

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.",

author = "Qiaogan Liao and Yulun Wang and Uddin, {Mohammad Afsar} and Jianhua Chen and Han Guo and Shengbin Shi and Yang Wang and Woo, {Han Young} and Xugang Guo",

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 {\textcopyright} 2018 American Chemical Society.",

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AU - Liao, Qiaogan

AU - Wang, Yulun

AU - Uddin, Mohammad Afsar

AU - Chen, Jianhua

AU - Guo, Han

AU - Shi, Shengbin

AU - Wang, Yang

AU - Woo, Han Young

AU - Guo, Xugang

N1 - 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.

PY - 2018/5/15

Y1 - 2018/5/15

N2 - 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.

AB - 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.

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

Abstract

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