Thiadiazole-fused Quinoxalineimide as an Electron-deficient Building Block for N-type Organic Semiconductors

Tsukasa Hasegawa; Minoru Ashizawa; Koutarou Aoyagi; Hiroyasu Masunaga; Takaaki Hikima; Hidetoshi Matsumoto

doi:10.1021/acs.orglett.7b01424

Thiadiazole-fused Quinoxalineimide as an Electron-deficient Building Block for N-type Organic Semiconductors

Org Lett. 2017 Jun 16;19(12):3275-3278. doi: 10.1021/acs.orglett.7b01424. Epub 2017 May 31.

Authors

Tsukasa Hasegawa¹, Minoru Ashizawa¹, Koutarou Aoyagi¹, Hiroyasu Masunaga², Takaaki Hikima³, Hidetoshi Matsumoto¹

Affiliations

¹ Department of Materials Science and Engineering, Tokyo Institute of Technology , 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.
² Japan Synchrotron Radiation Research Institute (JASRI)/SPring-8 , 1-1-1 Kouto, Sayo, Sayo 679-5198, Japan.
³ RIKEN SPring-8 Center , 1-1-1 Kouto, Sayo, Sayo 679-5148, Japan.

PMID: 28562059
DOI: 10.1021/acs.orglett.7b01424

Abstract

A strong electron-accepting planar π-conjugated framework, thiadiazole-fused quinoxalineimide (TQI), was designed and synthesized. Three TQI-based small molecules exhibit deep lowest-unoccupied molecular orbital (LUMO) levels, which require air stable n-channel conduction (∼-4.0 eV). Among these molecules, Hex-TQI-Br exhibits air-stable n-channel charge transport with a moderate mobility of 0.044 cm² V^-1 s^-1.

Publication types

Research Support, Non-U.S. Gov't