Air-Stable Benzo[ c]thiophene Diimide n-Type π-Electron Core

Craig P Yu; Ryoya Kimura; Tadanori Kurosawa; Eiji Fukuzaki; Tetsuya Watanabe; Hiroyuki Ishii; Shohei Kumagai; Masafumi Yano; Jun Takeya; Toshihiro Okamoto

doi:10.1021/acs.orglett.9b01239

Air-Stable Benzo[ c]thiophene Diimide n-Type π-Electron Core

Org Lett. 2019 Jun 21;21(12):4448-4453. doi: 10.1021/acs.orglett.9b01239. Epub 2019 Jun 5.

Authors

Affiliations

¹ Department of Advanced Materials Science, School of Frontier Sciences , The University of Tokyo , 5-1-5 Kashiwanoha, Kashiwa , Chiba 277-8561 , Japan.
² Chemistry, Materials and Bioengineering Major, Graduate School of Science and Engineering , Kansai University , 3-3-35 Yamate-cho, Suita , Osaka 564-8680 , Japan.
³ FUJIFILM Corp. , 577 Ushijima, Kaisei-machi, Ashigarakami-gun, Kanagawa 258-8577 , Japan.
⁴ Department of Applied Physics, Faculty of Pure and Applied Sciences , University of Tsukuba , 1-1-1 Tennodai, Tsukuba , Ibaraki 305-8573 , Japan.
⁵ PRESTO, JST , 4-1-8 Honcho, Kawaguchi, Saitama 332-0012 , Japan.

PMID: 31184164
DOI: 10.1021/acs.orglett.9b01239

Abstract

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.