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Z‐Shaped Pentaleno‐Acene Dimers with High Stability and Small Band Gap
Author(s) -
Dai Gaole,
Chang Jingjing,
Luo Jie,
Dong Shaoqiang,
Aratani Naoki,
Zheng Bin,
Huang KuoWei,
Yamada Hiroko,
Chi Chunyan
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508919
Subject(s) - acene , zigzag , materials science , acceptor , tetracene , pentalene , dimer , band gap , nanotechnology , photochemistry , crystallography , chemistry , optoelectronics , molecule , condensed matter physics , organic chemistry , physics , geometry , mathematics , anthracene
Acene‐based materials have promising applications for organic electronics but the major constrain comes from their poor stability. Herein a new strategy to stabilize reactive acenes, by fusion of an anti‐aromatic pentalene unit onto the zigzag edges of two acene units to form a Z‐shaped acene dimer, is introduced. The Z‐shaped acene dimers are extremely stable and show a small energy gap resulting from intramolecular donor–acceptor interactions. X‐ray crystallographic analysis revealed their unique geometry and one‐dimensional slip‐stack columnar structure. Besides optical and electrochemical characterizations, solution‐processed field‐effect transistors were also fabricated.