Organic Conductors with Narrow Bandwidth Based on 2-(Pyran-4-ylidene)-1,3-dithiole

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  • Takashi Shirahata
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
  • Masahide Ikeda
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
  • Hiroshi Watadzu
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan
  • Hideki Fujiwara
    Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Naka-ku, Sakai, Osaka 599-8531 , Japan
  • Takashi Maruyama
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501 , Japan
  • Tokio Yamabe
    Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501 , Japan
  • Yohji Misaki
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577 , Japan

抄録

<jats:title>Abstract</jats:title> <jats:p>A π-electron donor incorporating pyran-4-ylidene moiety, 2-(pyran-4-ylidene)-1,3-dithiole (PDT, 1a), and its derivatives (1b–e) have been synthesized. Cyclic voltammetry revealed that the derivatives of 1 exhibited two pairs of redox waves. Comparison of the first redox potentials (E1) indicated that the donating ability of PDT (E1 = −0.16 V vs. Fc/Fc+, in benzonitrile) is stronger than that of TTF (E1 = −0.09 V), but is weaker than the sulfur analog TPDT (E1 = −0.19 V). X-ray structure analyses of radical cation salts based on the ethylendithio derivative (1d)2X (X = ClO4, ReO4, and GaCl4) revealed that the donors form two-dimensional conducting sheets, in which the donors adopt the so-called β-type packing with a uniform head-to-tail stacking. Calculation of the overlap integrals of the HOMOs suggest that (1d)2X has a small intrastack overlap compared to the TTF-type conductors because of a head-to-tail stacking of the unsymmetrical π-electron framework. A tight-binding band calculation suggested that all the salts have quasi-one-dimensional Fermi surfaces. They exhibited relatively high conductivity of σrt = 0.79–20 S cm−1 on a single crystal and showed weak but metal-like temperature dependence of resistivity.</jats:p>

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