Intramolecular Locked Dithioalkylbithiophene-Based Semiconductors for High-Performance Organic Field-Effect Transistors

Sureshraju Vegiraju; Bo Chin Chang; Pragya Priyanka; Deng Yi Huang; Kuan Yi Wu; Long Huan Li; Wei Chieh Chang; Yi Yo Lai; Shao Huan Hong; Bo Chun Yu; Chien Lung Wang; Wen Jung Chang; Cheng Liang Liu; Ming Chou Chen; Antonio Facchetti

doi:10.1002/adma.201702414

Intramolecular Locked Dithioalkylbithiophene-Based Semiconductors for High-Performance Organic Field-Effect Transistors

Sureshraju Vegiraju, Bo Chin Chang, Pragya Priyanka, Deng Yi Huang, Kuan Yi Wu, Long Huan Li, Wei Chieh Chang, Yi Yo Lai, Shao Huan Hong, Bo Chun Yu, Chien Lung Wang, Wen Jung Chang, Cheng Liang Liu, Ming Chou Chen, Antonio Facchetti

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

New 3,3′-dithioalkyl-2,2′-bithiophene (SBT)-based small molecular and polymeric semiconductors are synthesized by end-capping or copolymerization with dithienothiophen-2-yl units. Single-crystal, molecular orbital computations, and optical/electrochemical data indicate that the SBT core is completely planar, likely via S(alkyl)⋯S(thiophene) intramolecular locks. Therefore, compared to semiconductors based on the conventional 3,3′-dialkyl-2,2′-bithiophene, the resulting SBT systems are planar (torsional angle <1°) and highly π-conjugated. Charge transport is investigated for solution-sheared films in field-effect transistors demonstrating that SBT can enable good semiconducting materials with hole mobilities ranging from ≈0.03 to 1.7 cm² V⁻¹ s⁻¹. Transport difference within this family is rationalized by film morphology, as accessed by grazing incidence X-ray diffraction experiments.

Original language	English
Article number	1702414
Journal	Advanced Materials
Volume	29
Issue number	35
DOIs	https://doi.org/10.1002/adma.201702414
State	Published - 20 Sep 2017

Keywords

dithienothiophene
dithioalkylbithiophene
organic field-effect transistors
solution-shearing

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10.1002/adma.201702414

CCDC 1547092: Experimental Crystal Structure Determination
Vegiraju, S. (Contributor), Chang, B.-C. (Contributor), Priyanka, P. (Contributor), Huang, D.-Y. (Contributor), Wu, K.-Y. (Contributor), Li, L.-H. (Contributor), Chang, W.-C. (Contributor), Lai, Y.-Y. (Contributor), Hong, S.-H. (Contributor), Yu, B.-C. (Contributor), Wang, C.-L. (Contributor), Chang, W.-J. (Contributor), Liu, C.-L. (Contributor), Chen, M.-C. (Contributor) & Facchetti, A. (Contributor), The Cambridge Structural Database, 2020
DOI: 10.5517/ccdc.csd.cc1nxw6n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nxw6n&sid=DataCite
Dataset
CCDC 1547094: Experimental Crystal Structure Determination
Vegiraju, S. (Contributor), Chang, B.-C. (Contributor), Priyanka, P. (Contributor), Huang, D.-Y. (Contributor), Wu, K.-Y. (Contributor), Li, L.-H. (Contributor), Chang, W.-C. (Contributor), Lai, Y.-Y. (Contributor), Hong, S.-H. (Contributor), Yu, B.-C. (Contributor), Wang, C.-L. (Contributor), Chang, W.-J. (Contributor), Liu, C.-L. (Contributor), Chen, M.-C. (Contributor) & Facchetti, A. (Contributor), The Cambridge Structural Database, 2020
DOI: 10.5517/ccdc.csd.cc1nxw8q, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nxw8q&sid=DataCite
Dataset

Cite this

Vegiraju, S., Chang, B. C., Priyanka, P., Huang, D. Y., Wu, K. Y., Li, L. H., Chang, W. C., Lai, Y. Y., Hong, S. H., Yu, B. C., Wang, C. L., Chang, W. J., Liu, C. L., Chen, M. C., & Facchetti, A. (2017). Intramolecular Locked Dithioalkylbithiophene-Based Semiconductors for High-Performance Organic Field-Effect Transistors. Advanced Materials, 29(35), Article 1702414. https://doi.org/10.1002/adma.201702414

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title = "Intramolecular Locked Dithioalkylbithiophene-Based Semiconductors for High-Performance Organic Field-Effect Transistors",

abstract = "New 3,3′-dithioalkyl-2,2′-bithiophene (SBT)-based small molecular and polymeric semiconductors are synthesized by end-capping or copolymerization with dithienothiophen-2-yl units. Single-crystal, molecular orbital computations, and optical/electrochemical data indicate that the SBT core is completely planar, likely via S(alkyl)⋯S(thiophene) intramolecular locks. Therefore, compared to semiconductors based on the conventional 3,3′-dialkyl-2,2′-bithiophene, the resulting SBT systems are planar (torsional angle <1°) and highly π-conjugated. Charge transport is investigated for solution-sheared films in field-effect transistors demonstrating that SBT can enable good semiconducting materials with hole mobilities ranging from ≈0.03 to 1.7 cm2 V−1 s−1. Transport difference within this family is rationalized by film morphology, as accessed by grazing incidence X-ray diffraction experiments.",

keywords = "dithienothiophene, dithioalkylbithiophene, organic field-effect transistors, solution-shearing",

author = "Sureshraju Vegiraju and Chang, {Bo Chin} and Pragya Priyanka and Huang, {Deng Yi} and Wu, {Kuan Yi} and Li, {Long Huan} and Chang, {Wei Chieh} and Lai, {Yi Yo} and Hong, {Shao Huan} and Yu, {Bo Chun} and Wang, {Chien Lung} and Chang, {Wen Jung} and Liu, {Cheng Liang} and Chen, {Ming Chou} and Antonio Facchetti",

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T1 - Intramolecular Locked Dithioalkylbithiophene-Based Semiconductors for High-Performance Organic Field-Effect Transistors

AU - Vegiraju, Sureshraju

AU - Chang, Bo Chin

AU - Priyanka, Pragya

AU - Huang, Deng Yi

AU - Wu, Kuan Yi

AU - Li, Long Huan

AU - Chang, Wei Chieh

AU - Lai, Yi Yo

AU - Hong, Shao Huan

AU - Yu, Bo Chun

AU - Wang, Chien Lung

AU - Chang, Wen Jung

AU - Liu, Cheng Liang

AU - Chen, Ming Chou

AU - Facchetti, Antonio

PY - 2017/9/20

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N2 - New 3,3′-dithioalkyl-2,2′-bithiophene (SBT)-based small molecular and polymeric semiconductors are synthesized by end-capping or copolymerization with dithienothiophen-2-yl units. Single-crystal, molecular orbital computations, and optical/electrochemical data indicate that the SBT core is completely planar, likely via S(alkyl)⋯S(thiophene) intramolecular locks. Therefore, compared to semiconductors based on the conventional 3,3′-dialkyl-2,2′-bithiophene, the resulting SBT systems are planar (torsional angle <1°) and highly π-conjugated. Charge transport is investigated for solution-sheared films in field-effect transistors demonstrating that SBT can enable good semiconducting materials with hole mobilities ranging from ≈0.03 to 1.7 cm2 V−1 s−1. Transport difference within this family is rationalized by film morphology, as accessed by grazing incidence X-ray diffraction experiments.

AB - New 3,3′-dithioalkyl-2,2′-bithiophene (SBT)-based small molecular and polymeric semiconductors are synthesized by end-capping or copolymerization with dithienothiophen-2-yl units. Single-crystal, molecular orbital computations, and optical/electrochemical data indicate that the SBT core is completely planar, likely via S(alkyl)⋯S(thiophene) intramolecular locks. Therefore, compared to semiconductors based on the conventional 3,3′-dialkyl-2,2′-bithiophene, the resulting SBT systems are planar (torsional angle <1°) and highly π-conjugated. Charge transport is investigated for solution-sheared films in field-effect transistors demonstrating that SBT can enable good semiconducting materials with hole mobilities ranging from ≈0.03 to 1.7 cm2 V−1 s−1. Transport difference within this family is rationalized by film morphology, as accessed by grazing incidence X-ray diffraction experiments.

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KW - dithioalkylbithiophene

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KW - solution-shearing

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DO - 10.1002/adma.201702414

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Intramolecular Locked Dithioalkylbithiophene-Based Semiconductors for High-Performance Organic Field-Effect Transistors

Abstract

Keywords

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Datasets

CCDC 1547092: Experimental Crystal Structure Determination

CCDC 1547094: Experimental Crystal Structure Determination

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