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 journalArticle

10 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

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Fluorination
Conformations
Polymers
Semiconductor materials
Hole mobility
Thin film transistors
Electric properties
Solubility
Annealing
benzo-1,2,3-thiadiazole
Temperature

ASJC Scopus subject areas

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

Cite this

Drastic Effects of Fluorination on Backbone Conformation of Head-to-Head Bithiophene-Based Polymer Semiconductors. / Liao, Qiaogan; Wang, Yulun; Uddin, Mohammad Afsar; Chen, Jianhua; Guo, Han; Shi, Shengbin; Wang, Yang; Woo, Han Young; Guo, Xugang.

In: ACS Macro Letters, Vol. 7, No. 5, 15.05.2018, p. 519-524.

Research output: Contribution to journalArticle

Liao, Qiaogan ; Wang, Yulun ; Uddin, Mohammad Afsar ; Chen, Jianhua ; Guo, Han ; Shi, Shengbin ; Wang, Yang ; Woo, Han Young ; Guo, Xugang. / Drastic Effects of Fluorination on Backbone Conformation of Head-to-Head Bithiophene-Based Polymer Semiconductors. In: ACS Macro Letters. 2018 ; Vol. 7, No. 5. pp. 519-524.
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