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Ambipolar Nickel Dithiolene Complex Semiconductors: From One- to Two-Dimensional Electronic Structures Based upon Alkoxy Chain Lengths

  • Masatoshi Ito
    Masatoshi Ito
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
  • Tomoko Fujino*
    Tomoko Fujino
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    *Email: [email protected]
  • Lei Zhang
    Lei Zhang
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    More by Lei Zhang
  • So Yokomori
    So Yokomori
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    More by So Yokomori
  • Toshiki Higashino
    Toshiki Higashino
    National Institute of Advanced Industrial Science and Technology, Tsukuba, Ibaraki 305-8565, Japan
  • Rie Makiura
    Rie Makiura
    Department of Materials Science, Graduate School of Engineering, Osaka Metropolitan University, Sakai, Osaka 599-8570, Japan
    More by Rie Makiura
  • Kanokwan Jumtee Takeno
    Kanokwan Jumtee Takeno
    Department of Materials Science, Graduate School of Engineering, Osaka Metropolitan University, Sakai, Osaka 599-8570, Japan
  • Taisuke Ozaki
    Taisuke Ozaki
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
  • , and 
  • Hatsumi Mori*
    Hatsumi Mori
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    *Email:[email protected]
    More by Hatsumi Mori
Cite this: J. Am. Chem. Soc. 2023, 145, 4, 2127–2134
Publication Date (Web):December 13, 2022
https://doi.org/10.1021/jacs.2c08015
Copyright © 2022 American Chemical Society

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    Abstract

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    Air-stable single-component ambipolar organic semiconductors that conduct both holes and electrons are highly desired but have been rarely realized. Neutral nickel bis(dithiolene) complexes are promising candidates that fulfill the stringent electronic requirements of shallow HOMO levels and deep LUMO levels, which can reduce the carrier injection barrier to overcome the work function of gold electrodes and ensure air stability. However, most nickel bis(dithiolene) analogs that have been characterized as ambipolar semiconductors have twisted molecular structures that hinder the effective intermolecular interactions required for carrier conduction. To address this issue, we synthesized planar alkoxy-substituted nickel bis(dithiolene) analogs that facilitate dense packing with effective intermolecular interactions. Remarkably, changing the methoxy substituents to ethoxy or propoxy groups led to a dramatic change in the packing mode, from one-dimensional to herringbone-like, while maintaining effective intermolecular interactions. These materials overcome the usual trade-off between crystallinity and solubility; they are highly crystalline, even in their film forms, and are highly soluble in organic solvents. They are therefore readily solution-processable to form semiconducting layers with well-defined and well-ordered structures in field-effect transistors. Devices based on these compounds exhibited efficient ambipolar characteristics, even after several months of exposure to air, achieving high carrier mobilities of up to 10–2 cm2 V–1 s–1 and large on/off ratios of up to 105, which are the top-class performances achieved for a single-component ambipolar semiconductor material driven in air.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c08015.

    • Synthetic procedures and characterization data, cyclic voltammograms, crystallographic data, calculation data, UV/vis/NIR absorption spectra of crystalline thin films, Tauc plots, FET fabrication, and evaluation method (PDF)

    Accession Codes

    CCDC 2165672, 21662702166271, and 2193009 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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