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Dodecatwistarene Imides with Zigzag‐Twisted Conformation for Organic Electronics
Author(s) -
Liu Guogang,
Xiao Chengyi,
Negri Fabrizia,
Li Yan,
Wang Zhaohui
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201912356
Subject(s) - zigzag , crystallography , steric effects , graphene , benzene , stille reaction , materials science , chemistry , orthorhombic crystal system , crystal structure , stereochemistry , nanotechnology , polymer , organic chemistry , geometry , mathematics
1D nonplanar graphene nanoribbons generally have three possible conformers: helical, zigzag, and mixed conformations. Now, a kind of 1D nonplanar graphene nanoribbon, namely dodecatwistarene imides featuring twelve linearly fused benzene rings, was obtained by bottom‐up synthesis of palladium‐catalyzed Stille coupling and C−H activation. Single‐crystal X‐ray diffraction analyses revealed that it displays a zigzag‐twisted conformation caused by steric hindrance between imide groups and neighboring annulated benzene rings with the pendulum angle of 53°. This conformation is very stable and could not convert into other conformations even when heated up to 250 °C for 6 h. Despite of the highly twisted topology, organic field‐effect transistor based on it exhibits electron mobility up to 1.5 cm 2 V −1 s −1 after annealing.