Head-to-Head Linked Dialkylbifuran-Based Polymer Semiconductors for High-Performance Organic Thin-Film Transistors with Tunable Charge Carrier Polarity

Shengbin Shi, Hang Wang, Mohammad Afsar Uddin, Kun Yang, Mengyao Su, Luca Bianchi, Peng Chen, Xing Cheng, Han Guo, Shiming Zhang, Han Young Woo, Xugang Guo

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A planar backbone conformation is essential for enabling polymer semiconductors with high charge carrier mobility in organic thin-film transistors. Benefiting from the smaller van der Waals radius of the O atom in furan (versus the S atom in thiophene), alkylated furan exerts a reduced steric hindrance on neighboring arene, and it was found that the head-to-head (HH)-linked 3,3′-dialkyl-2,2′-bifuran (BFR) can attain a high degree of backbone planarity. Hence, BFR should be a promising building block for constructing polymer semiconductors with a planar backbone conformation and hold distinctive advantages over a dialkylbithiophene-based analogue, which is typically highly twisted. The alkyl chains on the 3 and 3′ positions offer good solubility to the resulting polymers, which in combination with its planar backbone yields an improved molecular design window for developing high-performance polymer semiconductors, particularly those with a simple molecular structure and based on the acceptor co-unit without any solubilizing chains. When incorporated into polymer semiconductors, remarkably high hole and electron mobilities of 1.50 and 0.31 cm2 V-1 s-1 are obtained for BFR-based polymers FBFR-BO and CNBFR-C18 containing fluorinated and cyano-functionalized benzothiadiazole as the acceptor co-unit, respectively. Such mobilities are the highest values for HH-linked polymers and also among the best for furan-containing polymers. The results demonstrate that HH-linked dialkylbifuran is a highly promising building block for constructing organic and polymeric semiconductors, and this new approach by incorporating HH BFR offers several distinctive advantages for developing high-performance polymer semiconductors, including effective optoelectronic property tuning using a minimal number of aromatic rings, reduced structural complexity, facile material synthesis, good material solubility, and enriching the material library. In addition, the study offers important guidelines for future development of furan-based polymers and head-to-head linkage containing organic semiconductors.

Original languageEnglish
Pages (from-to)1808-1817
Number of pages10
JournalChemistry of Materials
Volume31
Issue number5
DOIs
Publication statusPublished - 2019 Mar 12

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Thin film transistors
Charge carriers
Polymers
Semiconductor materials
Conformations
Solubility
Thiophenes
Atoms
Hole mobility
Semiconducting organic compounds
Electron mobility
Carrier mobility
Thiophene
Optoelectronic devices
Molecular structure
Tuning
furan

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

Cite this

Head-to-Head Linked Dialkylbifuran-Based Polymer Semiconductors for High-Performance Organic Thin-Film Transistors with Tunable Charge Carrier Polarity. / Shi, Shengbin; Wang, Hang; Uddin, Mohammad Afsar; Yang, Kun; Su, Mengyao; Bianchi, Luca; Chen, Peng; Cheng, Xing; Guo, Han; Zhang, Shiming; Woo, Han Young; Guo, Xugang.

In: Chemistry of Materials, Vol. 31, No. 5, 12.03.2019, p. 1808-1817.

Research output: Contribution to journalArticle

Shi, Shengbin ; Wang, Hang ; Uddin, Mohammad Afsar ; Yang, Kun ; Su, Mengyao ; Bianchi, Luca ; Chen, Peng ; Cheng, Xing ; Guo, Han ; Zhang, Shiming ; Woo, Han Young ; Guo, Xugang. / Head-to-Head Linked Dialkylbifuran-Based Polymer Semiconductors for High-Performance Organic Thin-Film Transistors with Tunable Charge Carrier Polarity. In: Chemistry of Materials. 2019 ; Vol. 31, No. 5. pp. 1808-1817.
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abstract = "A planar backbone conformation is essential for enabling polymer semiconductors with high charge carrier mobility in organic thin-film transistors. Benefiting from the smaller van der Waals radius of the O atom in furan (versus the S atom in thiophene), alkylated furan exerts a reduced steric hindrance on neighboring arene, and it was found that the head-to-head (HH)-linked 3,3′-dialkyl-2,2′-bifuran (BFR) can attain a high degree of backbone planarity. Hence, BFR should be a promising building block for constructing polymer semiconductors with a planar backbone conformation and hold distinctive advantages over a dialkylbithiophene-based analogue, which is typically highly twisted. The alkyl chains on the 3 and 3′ positions offer good solubility to the resulting polymers, which in combination with its planar backbone yields an improved molecular design window for developing high-performance polymer semiconductors, particularly those with a simple molecular structure and based on the acceptor co-unit without any solubilizing chains. When incorporated into polymer semiconductors, remarkably high hole and electron mobilities of 1.50 and 0.31 cm2 V-1 s-1 are obtained for BFR-based polymers FBFR-BO and CNBFR-C18 containing fluorinated and cyano-functionalized benzothiadiazole as the acceptor co-unit, respectively. Such mobilities are the highest values for HH-linked polymers and also among the best for furan-containing polymers. The results demonstrate that HH-linked dialkylbifuran is a highly promising building block for constructing organic and polymeric semiconductors, and this new approach by incorporating HH BFR offers several distinctive advantages for developing high-performance polymer semiconductors, including effective optoelectronic property tuning using a minimal number of aromatic rings, reduced structural complexity, facile material synthesis, good material solubility, and enriching the material library. In addition, the study offers important guidelines for future development of furan-based polymers and head-to-head linkage containing organic semiconductors.",
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AU - Yang, Kun

AU - Su, Mengyao

AU - Bianchi, Luca

AU - Chen, Peng

AU - Cheng, Xing

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AU - Zhang, Shiming

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