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Boron-Stabilized Planar Neutral π-Radicals with Well-Balanced Ambipolar Charge-Transport Properties

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† Department of Chemistry, Graduate School of Science, Integrated Research Consortium on Chemical Sciences (IRCCS), and Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo, Chikusa, Nagoya 464-8602, Japan
‡ Department of Advanced Materials Science, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan
§ Division of Applied Physics, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
*[email protected]
*[email protected]
*[email protected]
Cite this: J. Am. Chem. Soc. 2017, 139, 41, 14336–14339
Publication Date (Web):October 4, 2017
https://doi.org/10.1021/jacs.7b05471
Copyright © 2017 American Chemical Society
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Abstract

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Organic neutral π-monoradicals are promising semiconductors with balanced ambipolar carrier-transport abilities, which arise from virtually identical spatial distribution of their singly occupied and unoccupied molecular orbitals, SOMO(α) and SOMO(β), respectively. Herein, we disclose a boron-stabilized triphenylmethyl radical that shows outstanding thermal stability and resistance toward atmospheric conditions due to the substantial spin delocalization. The radical is used to fabricate organic Mott-insulator transistors that operate at room temperature, wherein the radical exhibits well-balanced ambipolar carrier transport properties.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.7b05471.

  • Experimental details, crystal structures, and properties, as well as device fabrication protocols, including Scheme S1 and Figures S1–S26 (PDF)

  • X-ray crystallographic data for 1a, 1b, and 2 (CIF)

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