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Fused Pyrazine‐ and Carbazole‐Containing Azaacenes: Synthesis and Properties
Author(s) -
Liao Hailiang,
Xiao Chengyi,
Ravva Mahesh Kumar,
Yao Liping,
Yu Yaping,
Yang Yinghe,
Zhang Weimin,
Zhang Lei,
Li Zhengke,
McCulloch Iain,
Yue Wan
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900383
Subject(s) - pyrazine , carbazole , chemistry , ring (chemistry) , conjugated system , electron mobility , molecule , condensation , organic semiconductor , absorption (acoustics) , absorption spectroscopy , transistor , photochemistry , crystallography , optoelectronics , stereochemistry , polymer , organic chemistry , materials science , physics , quantum mechanics , composite material , thermodynamics , voltage
A new family of azaacenes has been designed and synthesized by incorporating the electron‐withdrawing sp 2 ‐hybridized nitrogen of pyrazine and electron‐donating nitrogen of carbazole in a molecular skeleton. Two different conjugated lengths of 8‐ring aza‐nonacene and 10‐ring aza‐undecene have been achieved by an efficient condensation reaction. The unique optoelectronic properties of these molecules were investigated using both experimental and theoretical techniques. The azaacenes show visible‐region absorption and near‐infrared (NIR) fluorescence. These compounds can serve as hole‐transport semiconductors for solution‐processed organic field‐effect transistors (OFETs). Single‐crystal transistor devices of one of the aza‐nonacenes exhibit hole charge transport behavior with a hole mobility of 0.07 cm 2 /Vs and an on/off current ratio of 1.3x10 6 .