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Spectroscopic and electrical characterization of α,γ-bisdiphenylene-β-phenylallyl radical as an organic semiconductor

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Abstract

The semiconductor properties of the earliest known stable radical, α,γ-bisdiphenylene-β-phenylallyl radical (Koelsch radical, 1•) were assessed using spectroscopic and electrical techniques. This radical undergoes reversible redox processes, and it has low redox potentials. In addition, 1• possesses long wavelength absorption bands, owing to the existence of a singly-occupied molecular orbital whose energy level lies between those of the HOMO and LUMO. A spin-coated thin-film of 1• displays photocurrent and an electron mobility of 6.3 × 10−7 cm2 V−1 s−1 on a trially-fabricated organic field effect transistor.

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Notes

  1. For the details, see the Supplementary Material.

  2. As an example of a DFT study of Radicals, see Ref. [22].

  3. The BDPA radical has been commercially available from Aldrich since February 2015. See: www.sigmaaldrich.com/catalog/product/aldrich/152560.

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Acknowledgements

The authors acknowledge valuable discussions with Mr. Yu Suenaga at OPU. This study was partially supported by JSPS KAKENHI grant numbers JP24109009 (Innovative Area Stimuli-responsive Chemical Species), JP17H01265, JP23350023, JP23108718 (pi-Space), JP21108520, JP21655016, and JP19350025. YM also acknowledges the Program to Disseminate Tenure Tracking System, MEXT, Japan.

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Authors and Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Yasunori Matsui, Minoru Shigemori, Takuya Ogaki, Eisuke Ohta, Kazuhiko Mizuno & Hiroshi Ikeda

  2. The Research Institute for Molecular Electronic Devices (RIMED), Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Yasunori Matsui, Takuya Ogaki, Eisuke Ohta, Hiroyoshi Naito & Hiroshi Ikeda

  3. Department of Physics and Electronics, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Toshiyuki Endo & Hiroyoshi Naito

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  1. Yasunori Matsui
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Correspondence to Hiroshi Ikeda.

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Matsui, Y., Shigemori, M., Endo, T. et al. Spectroscopic and electrical characterization of α,γ-bisdiphenylene-β-phenylallyl radical as an organic semiconductor. Res Chem Intermed 44, 4765–4774 (2018). https://doi.org/10.1007/s11164-018-3282-7

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