Open AccessSynthesis and Physicochemical Properties of Piceno[4,3-b:9,10-b′]dithiophene Derivatives and Their Application in Organic Field-Effect Transistors
Author(s) -
Keita Hyodo,
Ryota Toyama,
Hiroki Mori,
Yasushi Nishihara
Publication year - 2017
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.7b00015
Subject(s) - organic field effect transistor , negishi coupling , electron mobility , transistor , materials science , characterization (materials science) , field effect transistor , crystallography , homo/lumo , chemistry , stereochemistry , nanotechnology , catalysis , optoelectronics , molecule , organic chemistry , physics , quantum mechanics , voltage
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 (C 8 -PiDT) showed excellent hole mobility, as high as 2.36 cm 2 V -1 s -1 . Their structure-property relationships were investigated by X-ray diffraction and atomic force microscopy.