Synthesis and Properties of Tris-Fused Tetrathiafulvalene Analogues Possessing [3]Dendralene Moieties

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  • Kajiwara Yoshihiro
    Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University
  • Hino Shojun
    Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University
  • Misaki Yohji
    Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University

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New tris-fused tetrathiafulvalene analogues, in which the outer two TTF units were replaced by [3]dendralenes with triple 1,3-dithiole rings, were synthesized. A theoretical calculation of the unsubstituted derivative based on density functional theory (DFT) using B3LYP/6-31G(d) method suggested that branching 1,3-dithiole rings were almost perpendicular to the central TTF moiety. Cyclic voltammogram of the octakis(methylthio) derivative exhibited five pairs of redox waves at −0.03, 0.06, 0.37, 0.48, and 1.14 V (V vs. Fc/Fc+, in benzonitrile). The first, the second, and the fifth redox processes corresponded to simultaneous two-electron-transfer processes, while the others corresponded to one-electron transfer. The redox behavior and UV–vis–NIR spectra of the octamethyl derivative suggested that the positive charges in the dication and tetracation states distributed mainly on the outer branching vinylogous TTF moieties. A compressed pellet of the charge-transfer complexes of the octamethyl and octakis(methylthio) derivatives with TCNQF4 exhibited moderate conductivity of σrt = 10−3 S cm−1 and semiconductive behavior with activation energies of 0.10–0.13 eV.

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