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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2019, 21, 12, 4448-4453
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Air-Stable Benzo[c]thiophene Diimide n-Type π-Electron Core

  • Craig P. Yu
    Craig P. Yu
    Department of Advanced Materials Science, School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan
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    Orcidhttp://orcid.org/0000-0002-1423-5244
    • , 
  • Ryoya Kimura
    Ryoya Kimura
    Chemistry, Materials and Bioengineering Major, Graduate School of Science and Engineering, Kansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japan
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    • , 
  • Tadanori Kurosawa
    Tadanori Kurosawa
    Department of Advanced Materials Science, School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan
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    • , 
  • Eiji Fukuzaki
    Eiji Fukuzaki
    FUJIFILM Corp., 577 Ushijima, Kaisei-machi, Ashigarakami-gun, Kanagawa 258-8577, Japan
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    • , 
  • Tetsuya Watanabe
    Tetsuya Watanabe
    FUJIFILM Corp., 577 Ushijima, Kaisei-machi, Ashigarakami-gun, Kanagawa 258-8577, Japan
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    • , 
  • Hiroyuki Ishii
    Hiroyuki Ishii
    Department of Applied Physics, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
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    • , 
  • Shohei Kumagai
    Shohei Kumagai
    Department of Advanced Materials Science, School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan
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    Orcidhttp://orcid.org/0000-0002-1554-054X
    • , 
  • Masafumi Yano
    Masafumi Yano
    Chemistry, Materials and Bioengineering Major, Graduate School of Science and Engineering, Kansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japan
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    • , 
  • Jun Takeya
    Jun Takeya
    Department of Advanced Materials Science, School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan
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    • , and 
  • Toshihiro Okamoto*
    Toshihiro Okamoto
    Department of Advanced Materials Science, School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan
    PRESTO, JST, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
    *E-mail: [email protected]
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    Orcidhttp://orcid.org/0000-0002-4783-0621
Cite this: Org. Lett. 2019, 21, 12, 4448–4453
Publication Date (Web):June 5, 2019
https://doi.org/10.1021/acs.orglett.9b01239
Copyright © 2019 American Chemical Society
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Abstract

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In this paper, the molecular design of the first deep-lowest unoccupied molecular orbital (LUMO) level diimide π-electron core, benzo[c]thiophene diimide (BTDI), as a novel n-type organic semiconductor was determined. An original synthetic sequence was devised to obtain the target cyclohexyl-BTDI (Cy6-BTDI) derivative. Cy6-BTDI demonstrated completely reversible reduction waves and a stable radical anionic state. Favorable brickwork molecular assembly and two-dimensional charge transport properties of Cy6-BTDI were exhibited in the solid state. As a result, air-stable electron mobilities were obtained from the BTDI organic field-effect transistors under ambient conditions.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b01239.

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Cited By

This article is cited by 7 publications.

  1. John A. Joule. Five-membered ring systems: thiophenes and selenium/tellurium analogs and benzo analogs. 2021,,, 163-192. https://doi.org/10.1016/B978-0-323-89812-6.00005-5
  2. . . 2021,,https://doi.org/
  3. Xiaolong Chen, Dongwei Zhang, Yaowu He, Muhammad Umair Ali, Yuting Wu, Changbin Zhao, Peiheng Wu, Chaoyi Yan, Fred Wudl, Hong Meng. Fluoro-alkyl substituted isothianaphthene bisimides as stable n-type semiconductors. Materials Chemistry Frontiers 2020, 4 (12) , 3578-3584. https://doi.org/10.1039/D0QM00137F
  4. Zhichao Wang, Qinqin Peng, Xuan Huang, Qianli Ma, Qian Shen, Jinjun Shao. Linear acenaphthene-imide-fused pyrazinacene-quinone: synthesis and photophysical properties. Materials Technology 2020, 107 , 1-8. https://doi.org/10.1080/10667857.2020.1810925
  5. Laura Abad Galán, José M. Andrés Castán, Clément Dalinot, Pablo Simón Marqués, Philippe Blanchard, Olivier Maury, Clément Cabanetos, Tangui Le Bahers, Cyrille Monnereau. Theoretical and experimental investigation on the intersystem crossing kinetics in benzothioxanthene imide luminophores, and their dependence on substituent effects. Physical Chemistry Chemical Physics 2020, 22 (22) , 12373-12381. https://doi.org/10.1039/D0CP01072C
  6. Rudranarayan Khatua, Suryakanti Debata, Sridhar Sahu. Computational characterization of N-type characteristics and optoelectronic properties in air-stable pyromellitic diimide derivatives. New Journal of Chemistry 2020, 44 (20) , 8412-8421. https://doi.org/10.1039/D0NJ00811G
  7. Xiaolong Chen, Yaowu He, Muhammad Umair Ali, Yu He, Yanan Zhu, Aiyuan Li, Changbin Zhao, Igor F. Perepichka, Hong Meng. Isothianaphthene diimide: an air-stable n-type semiconductor. Science China Chemistry 2019, 62 (10) , 1360-1364. https://doi.org/10.1007/s11426-019-9555-4

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