Synthesis and Physicochemical Properties of Piceno[4,3- b:9,10- b']dithiophene Derivatives and Their Application in Organic Field-Effect Transistors

Keita Hyodo; Ryota Toyama; Hiroki Mori; Yasushi Nishihara

doi:10.1021/acsomega.7b00015

Synthesis and Physicochemical Properties of Piceno[4,3- b:9,10- b']dithiophene Derivatives and Their Application in Organic Field-Effect Transistors

ACS Omega. 2017 Jan 30;2(1):308-315. doi: 10.1021/acsomega.7b00015. eCollection 2017 Jan 31.

Authors

Keita Hyodo¹, Ryota Toyama¹, Hiroki Mori¹, Yasushi Nishihara¹

Affiliation

¹ Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology and Research Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.

Abstract

Efficient synthesis and characterization of several piceno[4,3-b:9,10-b']dithiophene (PiDT) derivatives by Negishi coupling, epoxidation, and Lewis acid-catalyzed cycloaromatization sequences and their potential utility in organic field-effect transistors (OFETs) have been reported. PiDT derivatives, with extended π-electron systems, showed high air stability due to their deep highest occupied molecular orbital energy levels (around -5.6 eV). OFET devices based on 2,11-dioctylated PiDT (C₈-PiDT) showed excellent hole mobility, as high as 2.36 cm² V^-1 s^-1. Their structure-property relationships were investigated by X-ray diffraction and atomic force microscopy.