Syn-/anti-anthradithiophene derivative isomer effects on semiconducting properties

Masashi Mamada, Hiroshi Katagiri, Makoto Mizukami, Kota Honda, Tsukuru Minamiki, Ryo Teraoka, Taisuke Uemura, Shizuo Tokito

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59 Citations (Scopus)


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-/anti-anthradithiophenes were nearly the in the solid state as well as in solution. However, field-effect transistors showed obvious differences with mobilities of 0.12 cm2 V-1 s-1 for anti-anthradithiophene and 0.02 cm2 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.

Original languageEnglish
Pages (from-to)9670-9677
Number of pages8
JournalACS Applied Materials and Interfaces
Issue number19
Publication statusPublished - Oct 9 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Materials Science(all)


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