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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.

Citation

Takakazu Kimoto, Kenro Tanaka, Masatoshi Kawahata, Kentaro Yamaguchi, Saika Otsubo, Yoshimasa Sakai, Yuuki Ono, Akira Ohno, Kenji Kobayashi. Bis(methylthio)tetracenes: synthesis, crystal-packing structures, and OFET properties. The Journal of organic chemistry. 2011 Jun 17;76(12):5018-25

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PMID: 21568347

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