Bis(methylthio)tetracenes: Synthesis, Crystal-Packing Structures, and OFET Properties
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- Takakazu Kimoto
- Department of Chemistry, Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan,
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- Kenro Tanaka
- Department of Chemistry, Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan,
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- Masatoshi Kawahata
- Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Shido, Sanuki, Kagawa 769-2193, Japan, and
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- Kentaro Yamaguchi
- Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Shido, Sanuki, Kagawa 769-2193, Japan, and
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- Saika Otsubo
- Mitsubishi Chemical Group Science and Technology Research Center, Inc., 1000 Kamoshida, Aoba-ku, Yokohama 227-8502, Japan
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- Yoshimasa Sakai
- Mitsubishi Chemical Group Science and Technology Research Center, Inc., 1000 Kamoshida, Aoba-ku, Yokohama 227-8502, Japan
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- Yuuki Ono
- Mitsubishi Chemical Group Science and Technology Research Center, Inc., 1000 Kamoshida, Aoba-ku, Yokohama 227-8502, Japan
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- Akira Ohno
- Mitsubishi Chemical Group Science and Technology Research Center, Inc., 1000 Kamoshida, Aoba-ku, Yokohama 227-8502, Japan
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- Kenji Kobayashi
- Department of Chemistry, Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan,
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説明
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.
収録刊行物
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- The Journal of Organic Chemistry
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The Journal of Organic Chemistry 76 (12), 5018-5025, 2011-05-25
American Chemical Society (ACS)
