Novel Oxygen-Containing π-Electron Donors for Organic Metals:  2-(1,3-Dithiol-2-ylidene)-5-(pyran-4-ylidene)- 1,3,4,6-tetrathiapentalenes

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  • Yohji Misaki
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan, Department of Organic and Polymeric Materials, Faculty of Engineering, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan, and International Superconductivity Technology Center, Shinonome, Tokyo 135-0062, Japan
  • Hideki Fujiwara
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan, Department of Organic and Polymeric Materials, Faculty of Engineering, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan, and International Superconductivity Technology Center, Shinonome, Tokyo 135-0062, Japan
  • Takashi Maruyama
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan, Department of Organic and Polymeric Materials, Faculty of Engineering, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan, and International Superconductivity Technology Center, Shinonome, Tokyo 135-0062, Japan
  • Masateru Taniguchi
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan, Department of Organic and Polymeric Materials, Faculty of Engineering, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan, and International Superconductivity Technology Center, Shinonome, Tokyo 135-0062, Japan
  • Tokio Yamabe
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan, Department of Organic and Polymeric Materials, Faculty of Engineering, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan, and International Superconductivity Technology Center, Shinonome, Tokyo 135-0062, Japan
  • Takehiko Mori
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan, Department of Organic and Polymeric Materials, Faculty of Engineering, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan, and International Superconductivity Technology Center, Shinonome, Tokyo 135-0062, Japan
  • Hatsumi Mori
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan, Department of Organic and Polymeric Materials, Faculty of Engineering, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan, and International Superconductivity Technology Center, Shinonome, Tokyo 135-0062, Japan
  • Shoji Tanaka
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan, Department of Organic and Polymeric Materials, Faculty of Engineering, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan, and International Superconductivity Technology Center, Shinonome, Tokyo 135-0062, Japan

説明

A bis-fused π-electron donor incorporating a pyran-4-ylidene moiety, 2-(1,3-dithiol-2-ylidene)-5-(pyran-4-ylidene)-1,3,4,6-tetrathiapentalene (PDT−TTP, 1a), and its derivatives (1b−d) have been synthesized. The cyclic voltammograms of PDT−TTPs are composed of three pairs of redox waves. Comparison of the first oxidation potentials (E1) suggests PDT−TTP (+0.42 V vs SCE in benzonitrile) is a weaker donor than TTF (+0.35 V). The present donors have produced a large number of highly conducting (σrt = 100−102 S cm-1) molecular complexes. Among them, conducting salts based on the ET−PDT (1d) are metallic down to liquid helium temperature. The metallic PF6- salt of ET−PDT has a composition of (ET−PDT)4PF6(cn), where cn is 1-chloronaphthalene, in which two crystallographically independent ET−PDT molecules A and B form a face-to-face stack with a four-folded period as A‘ABB‘. In the present salt, the head-to-tail overlap of the unsymmetrical π-electron framework of PDT−TTP prevents an effective intrastack overlap ...

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