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n‐Type Azaacenes Containing B←N Units
Author(s) -
Min Yang,
Dou Chuandong,
Tian Hongkun,
Geng Yanhou,
Liu Jun,
Wang Lixiang
Publication year - 2018
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.201712986
Subject(s) - delocalized electron , acene , aromaticity , chemistry , boron , type (biology) , homo/lumo , crystallography , stereochemistry , ring (chemistry) , molecule , organic chemistry , ecology , biology
We disclose a novel strategy to design n‐type acenes through the introduction of boron–nitrogen coordination bonds (B←N). We synthesized two azaacenes composed of two B←N units and six/eight linearly annelated rings. The B←N unit significantly perturbed the electronic structures of the azaacenes: Unique LUMOs delocalized over the entire acene skeletons and decreased aromaticity of the B←N‐adjacent rings. Most importantly, these B←N‐containing azaacenes exhibited low‐lying LUMO energy levels and high electron affinities, thus leading to n‐type character. The solution‐processed organic field‐effect transistor based on one such azaacene exhibited unipolar n‐type characteristics with an electron mobility of 0.21 cm 2 V −1 s −1 .