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Synthesis, Structure, and Air‐stable N‐type Field‐Effect Transistor Behaviors of Functionalized Octaazanonacene‐8,19‐dione
Author(s) -
Wang Chengyuan,
Zhang Jing,
Long Guankui,
Aratani Naoki,
Yamada Hiroko,
Zhao Yang,
Zhang Qichun
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201500972
Subject(s) - electron mobility , field effect transistor , transistor , materials science , conjugated system , homo/lumo , degradation (telecommunications) , nanotechnology , optoelectronics , chemistry , polymer , organic chemistry , electrical engineering , molecule , telecommunications , computer science , voltage , composite material , engineering
Increasing the length of N‐heteroacenes or their analogues is highly desirable because such materials could have great potential applications in organic electronics. In this report, the large π‐conjugated N‐heteroquinone 6,10,17,21‐tetra‐((triisopropylsilyl)ethynyl)‐5,7,9,11,16,18,20,22‐octaazanonacene‐8,19‐dione (OANQ) has been synthesized and characterized. The as‐prepared OANQ shows high stability under ambient conditions and has a particularly low LUMO level, which leads to it being a promising candidate for air‐stable n‐type field‐effect transistors (FETs). In fact, FET devices based on OANQ single crystals have been fabricated and an electron mobility of up to 0.2 cm 2 V −1 s −1 under ambient conditions is reported. More importantly, no obvious degradation was observed even after one month. Theoretical calculations based on the single crystal are consistent with the measured mobility.