Bis(methylthio)tetracenes: Synthesis, Crystal-Packing Structures, and OFET Properties

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• 作者：Takakazu Kimoto ; Kenro Tanaka ; Masatoshi Kawahata ; Kentaro Yamaguchi ; Saika Otsubo ; Yoshimasa Sakai ; Yuuki Ono ; Akira Ohno ; Kenji Kobayashi
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：June 17, 2011
• 年：2011
• 卷：76
• 期：12
• 页码：5018-5025
• 全文大小：1159K
• 年卷期：v.76,no.12(June 17, 2011)
• ISSN：1520-6904

文摘

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鈥?.24 eV and their HOMO鈥揕UMO 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 蟺-stacking with S鈥揝 and S鈭捪€ interactions, similar to the packing arrangement of 6,13-bis(methylthio)pentacene (1), whereas 3 exhibits a herringbone packing arrangement without S鈥揝 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 脳 10^鈥? and 4.0 脳 10^鈥? cm² V^鈥? s^鈥? with current on/off ratios of over 10⁵ and 10⁴, respectively.