Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 5, Issue 19, Pages 9670-9677Publisher
AMER CHEMICAL SOC
DOI: 10.1021/am4027136
Keywords
organic field-effect transistors; organic semiconductors; thienoacenes; symmetry; crystal structures
Funding
- Japan Science and Technology Agency (JST)
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- UBE foundation
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Isomerically pure syn-/anti-anthradithiophene derivatives have been developed in the past few years. Although anti-isomers showed higher field-effect mobilities than mixture of isomers have been reported, a detailed comparison of syn-isomer and anti-isomer molecules has not been carried out. In this study, we took newly synthesized pure unsubstituted syn-/anti-anthradithiophenes (ADTs) and compared their single crystal structures, physical properties and semiconducting behavior with a previously studied syn-/anti-dimethylanthradithiophenes (DMADTs). Although the both isomers were typical herringbone packing structures with similar parameters, anti-isomers involved less disordered atoms in the crystal packing. The results from thermal analysis, UV vis spectra, photo luminescence spectra and cyclic voltammograms of syn-/antianthradithiophenes were nearly the in the solid state as well as in solution. However, field-effect transistors showed obvious differences with mobilities of 0.12 cm(2) V-1 s(-1) for anti-anthradithiophene and 0.02 cm(2) V-1 s(-1) for syn-anthradithiophene. Because the crystallinity of thin-films measured by X-ray diffraction (XRD) and atomic force microscopy (AFM) seems to be better in syn-isomers, the differences in transistor performance are likely attributed to local defects affecting intermolecular interactions, such as disorder in the crystal packing and charge-dipole interactions.
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