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

Tomokatsu Kushida^†, Shusuke Shirai^†, Naoki Ando^†, Toshihiro Okamoto^*^‡, Hiroyuki Ishii^§, Hiroyuki Matsui^‡, Masakazu Yamagishi^‡, Takafumi Uemura^‡, Junto Tsurumi^‡, Shun Watanabe^‡

, Jun Takeya^*^‡, and Shigehiro Yamaguchi^*^†

^† 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

J. Am. Chem. Soc., 2017, 139 (41), pp 14336–14339

DOI: 10.1021/jacs.7b05471

Publication Date (Web): October 4, 2017

*tokamoto@edu.k.u-tokyo.ac.jp, *takeya@k.u-tokyo.ac.jp, *yamaguchi@chem.nagoya-u.ac.jp

Cite this:J. Am. Chem. Soc. 139, 41, 14336-14339

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Abstract

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.

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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