Bis(methylthio)tetracenes: Synthesis, Crystal-Packing Structures, and OFET Properties
| Autor: | Saika Otsubo, Yuuki Ono, Kenro Tanaka, Takakazu Kimoto, Yoshimasa Sakai, Kentaro Yamaguchi, Akira Ohno, Masatoshi Kawahata, Kenji Kobayashi |
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| Rok vydání: | 2011 |
| Předmět: |
Models
Molecular Organic field-effect transistor Naphthacenes Chemistry Stereochemistry Organic Chemistry Molecular Conformation X-ray Crystallographic data Crystallography X-Ray Microscopy Atomic Force Methylation Molecular conformation Crystal Pentacene Crystallography chemistry.chemical_compound Tetracene Sulfhydryl Compounds HOMO/LUMO |
| Zdroj: | The Journal of Organic Chemistry. 76:5018-5025 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo200696a |
| Popis: | 5,12-Bis(methylthio)tetracene (2) and 5,11-bis(methylthio)tetracene (3) were synthesized. DFT calculations indicate that the HOMO and LUMO energy levels of 2 and 3 are lowered by 0.13-0.24 eV and their HOMO-LUMO energy gaps are reduced by 0.1 eV relative to those of tetracene. X-ray crystallographic data revealed that 2 is arranged as a result of a 1-D slipped-cofacial π-stacking with S-S and S-π interactions, similar to the packing arrangement of 6,13-bis(methylthio)pentacene (1), whereas 3 exhibits a herringbone packing arrangement without S-S interactions. The OFET devices fabricated using spin-coated films of soluble 1 and 2, with a bottom-contact device configuration, exhibited hole mobilities as high as 1.3 × 10(-2) and 4.0 × 10(-2) cm(2) V(-1) s(-1) with current on/off ratios of over 10(5) and 10(4), respectively. |
| Databáze: | OpenAIRE |
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