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Thienoacene‐Fused Pentalenes: Syntheses, Structures, Physical Properties and Applications for Organic Field‐Effect Transistors
Author(s) -
Dai Gaole,
Chang Jingjing,
Shi Xueliang,
Zhang Wenhua,
Zheng Bin,
Huang KuoWei,
Chi Chunyan
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405652
Subject(s) - pentalene , antiaromaticity , moiety , density functional theory , materials science , thermal stability , band gap , absorption spectroscopy , electronic structure , absorption (acoustics) , computational chemistry , chemistry , crystallography , aromaticity , optoelectronics , molecule , stereochemistry , organic chemistry , physics , quantum mechanics , composite material
Three soluble and stable thienoacene‐fused pentalene derivatives ( 1 – 3 ) with different π‐conjugation lengths were synthesized. X‐ray crystallographic analysis and density functional theory (DFT) calculations revealed their unique geometric and electronic structures due to the interaction between the aromatic thienoacene units and antiaromatic pentalene moiety. As a result, they all possess a small energy gap and show amphoteric redox behaviour. Time dependent (TD) DFT calculations were used to explain their unique electronic absorption spectra. These new compounds exhibited good thermal stability and ordered packing in solid state and thus their applications in organic field‐effect transistors (OFETs) were also investigated. The highest field‐effect hole mobility of 0.016, 0.036 and 0.001 cm 2 V −1 s −1 was achieved for solution‐processed thin films of 1 – 3 , respectively.