Quinoidal thioalkyl-substituted bithiophene small molecule semiconductors for n-type organic field effect transistors

Vellaichamy Joseph; Chih Hsin Yu; Chia Chi Lin; Wei Chieh Lien; Hsin Chia Tsai; Cheng Shiun Chen; Alfonsina Abat Amelenan Torimtubun; Arulmozhi Velusamy; Ping Yu Huang; Gene Hsiang Lee; Shueh Lin Yau; Shih Hung Tung; Takeo Minari; Cheng Liang Liu; Ming Chou Chen

doi:10.1039/d0tc03808c

Quinoidal thioalkyl-substituted bithiophene small molecule semiconductors for n-type organic field effect transistors

Vellaichamy Joseph, Chih Hsin Yu, Chia Chi Lin, Wei Chieh Lien, Hsin Chia Tsai, Cheng Shiun Chen, Alfonsina Abat Amelenan Torimtubun, Arulmozhi Velusamy, Ping Yu Huang, Gene Hsiang Lee, Shueh Lin Yau, Shih Hung Tung, Takeo Minari, Cheng Liang Liu, Ming Chou Chen

Department of Chemistry

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

12 Scopus citations

Abstract

Two tetrathioalkyl-substituted bithiophene-based small molecule quinoids (TSBTQs) having different chain lengths (thio-hexyl and -decyl) are synthesized and applied as an n-type active component in organic field effect transistors (OFETs). The resulting two TSBTQs exhibit good solubility in various organic solvents and LUMO levels below -4.0 eV. The theoretical DFT calculation supported by single crystal structures confirms the π-conjugated backbone planarity due to the S(thiophene)⋯S(alkyl) non-covalent interaction. Optimized TSBQT-10 OFETs exhibit an electron mobility of 0.18 cm2 V-1 s-1, which is higher than that of TSBTQ-6 (0.09 cm2 V-1 s-1). The reliability of the OFETs under representative environmental and operational conditions is also determined. The effects of side chains including their lengths and contribution to the main chain π-system coplanarity presented here demonstrate an efficient method to manipulate the charge carrier mobility of the quinoidal organic semiconductors. This journal is

Original language	English
Pages (from-to)	15450-15458
Number of pages	9
Journal	Journal of Materials Chemistry C
Volume	8
Issue number	43
DOIs	https://doi.org/10.1039/d0tc03808c
State	Published - 21 Nov 2020

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10.1039/d0tc03808c

產學研發中心計畫—中央大學-DSM聯合研發中心:綠色先進功能性材料開發與製程研究(1/3)
Lii, K.-H. (PI)
1/07/20 → 30/06/21
Project: Research

CCDC 1993957: Experimental Crystal Structure Determination
Joseph, V. (Contributor), Yu, C.-H. (Contributor), Lin, C.-C. (Contributor), Lien, W.-C. (Contributor), Tsai, H.-C. (Contributor), Chen, C.-S. (Contributor), Torimtubun, A. A. A. (Contributor), Velusamy, A. (Contributor), Huang, P.-Y. (Contributor), Lee, G.-H. (Contributor), Yau, S.-L. (Contributor), Tung, S.-H. (Contributor), Minari, T. (Contributor), Liu, C.-L. (Contributor) & Chen, M.-C. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc24xw65, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc24xw65&sid=DataCite
Dataset

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Joseph, V., Yu, C. H., Lin, C. C., Lien, W. C., Tsai, H. C., Chen, C. S., Torimtubun, A. A. A., Velusamy, A., Huang, P. Y., Lee, G. H., Yau, S. L., Tung, S. H., Minari, T., Liu, C. L., & Chen, M. C. (2020). Quinoidal thioalkyl-substituted bithiophene small molecule semiconductors for n-type organic field effect transistors. Journal of Materials Chemistry C, 8(43), 15450-15458. https://doi.org/10.1039/d0tc03808c

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title = "Quinoidal thioalkyl-substituted bithiophene small molecule semiconductors for n-type organic field effect transistors",

abstract = "Two tetrathioalkyl-substituted bithiophene-based small molecule quinoids (TSBTQs) having different chain lengths (thio-hexyl and -decyl) are synthesized and applied as an n-type active component in organic field effect transistors (OFETs). The resulting two TSBTQs exhibit good solubility in various organic solvents and LUMO levels below -4.0 eV. The theoretical DFT calculation supported by single crystal structures confirms the π-conjugated backbone planarity due to the S(thiophene)⋯S(alkyl) non-covalent interaction. Optimized TSBQT-10 OFETs exhibit an electron mobility of 0.18 cm2 V-1 s-1, which is higher than that of TSBTQ-6 (0.09 cm2 V-1 s-1). The reliability of the OFETs under representative environmental and operational conditions is also determined. The effects of side chains including their lengths and contribution to the main chain π-system coplanarity presented here demonstrate an efficient method to manipulate the charge carrier mobility of the quinoidal organic semiconductors. This journal is ",

author = "Vellaichamy Joseph and Yu, {Chih Hsin} and Lin, {Chia Chi} and Lien, {Wei Chieh} and Tsai, {Hsin Chia} and Chen, {Cheng Shiun} and Torimtubun, {Alfonsina Abat Amelenan} and Arulmozhi Velusamy and Huang, {Ping Yu} and Lee, {Gene Hsiang} and Yau, {Shueh Lin} and Tung, {Shih Hung} and Takeo Minari and Liu, {Cheng Liang} and Chen, {Ming Chou}",

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doi = "10.1039/d0tc03808c",

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Joseph, V, Yu, CH, Lin, CC, Lien, WC, Tsai, HC, Chen, CS, Torimtubun, AAA, Velusamy, A, Huang, PY, Lee, GH, Yau, SL, Tung, SH, Minari, T, Liu, CL & Chen, MC 2020, 'Quinoidal thioalkyl-substituted bithiophene small molecule semiconductors for n-type organic field effect transistors', Journal of Materials Chemistry C, vol. 8, no. 43, pp. 15450-15458. https://doi.org/10.1039/d0tc03808c

TY - JOUR

T1 - Quinoidal thioalkyl-substituted bithiophene small molecule semiconductors for n-type organic field effect transistors

AU - Joseph, Vellaichamy

AU - Yu, Chih Hsin

AU - Lin, Chia Chi

AU - Lien, Wei Chieh

AU - Tsai, Hsin Chia

AU - Chen, Cheng Shiun

AU - Torimtubun, Alfonsina Abat Amelenan

AU - Velusamy, Arulmozhi

AU - Huang, Ping Yu

AU - Lee, Gene Hsiang

AU - Yau, Shueh Lin

AU - Tung, Shih Hung

AU - Minari, Takeo

AU - Liu, Cheng Liang

AU - Chen, Ming Chou

PY - 2020/11/21

Y1 - 2020/11/21

N2 - Two tetrathioalkyl-substituted bithiophene-based small molecule quinoids (TSBTQs) having different chain lengths (thio-hexyl and -decyl) are synthesized and applied as an n-type active component in organic field effect transistors (OFETs). The resulting two TSBTQs exhibit good solubility in various organic solvents and LUMO levels below -4.0 eV. The theoretical DFT calculation supported by single crystal structures confirms the π-conjugated backbone planarity due to the S(thiophene)⋯S(alkyl) non-covalent interaction. Optimized TSBQT-10 OFETs exhibit an electron mobility of 0.18 cm2 V-1 s-1, which is higher than that of TSBTQ-6 (0.09 cm2 V-1 s-1). The reliability of the OFETs under representative environmental and operational conditions is also determined. The effects of side chains including their lengths and contribution to the main chain π-system coplanarity presented here demonstrate an efficient method to manipulate the charge carrier mobility of the quinoidal organic semiconductors. This journal is

AB - Two tetrathioalkyl-substituted bithiophene-based small molecule quinoids (TSBTQs) having different chain lengths (thio-hexyl and -decyl) are synthesized and applied as an n-type active component in organic field effect transistors (OFETs). The resulting two TSBTQs exhibit good solubility in various organic solvents and LUMO levels below -4.0 eV. The theoretical DFT calculation supported by single crystal structures confirms the π-conjugated backbone planarity due to the S(thiophene)⋯S(alkyl) non-covalent interaction. Optimized TSBQT-10 OFETs exhibit an electron mobility of 0.18 cm2 V-1 s-1, which is higher than that of TSBTQ-6 (0.09 cm2 V-1 s-1). The reliability of the OFETs under representative environmental and operational conditions is also determined. The effects of side chains including their lengths and contribution to the main chain π-system coplanarity presented here demonstrate an efficient method to manipulate the charge carrier mobility of the quinoidal organic semiconductors. This journal is

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U2 - 10.1039/d0tc03808c

DO - 10.1039/d0tc03808c

M3 - 期刊論文

AN - SCOPUS:85096233542

SN - 2050-7534

VL - 8

SP - 15450

EP - 15458

JO - Journal of Materials Chemistry C

JF - Journal of Materials Chemistry C

IS - 43

ER -

Quinoidal thioalkyl-substituted bithiophene small molecule semiconductors for n-type organic field effect transistors

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產學研發中心計畫—中央大學-DSM聯合研發中心:綠色先進功能性材料開發與製程研究(1/3)

Datasets

CCDC 1993957: Experimental Crystal Structure Determination

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