Dimeric and Trimeric Tetrathiafulvalenes with Strong Intramolecular Interactions in the Oxidized States

  • Ken-ichi Nakamura
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan, and Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato. Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
  • Tsuyoshi Takashima
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan, and Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato. Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
  • Takashi Shirahata
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan, and Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato. Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
  • Shojun Hino
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan, and Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato. Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
  • Masashi Hasegawa
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan, and Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato. Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
  • Yasuhiro Mazaki
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan, and Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato. Minami-ku, Sagamihara, Kanagawa 252-0373, Japan
  • Yohji Misaki
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan, and Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato. Minami-ku, Sagamihara, Kanagawa 252-0373, Japan

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Description

New dimeric and trimeric TTF derivatives with methylenedithio spacers (1a,b, 2a, and 2b) have been synthesized. X-ray structure analysis revealed that TTF units of the dimer 1b adopted distorted face-to-face overlapping arrangement both in intra- and intermolecular stacking. Cyclic voltammetric study indicated that trimeric 2a was in favor of taking di- and tetracationic states, while the dimeric 1a was in favor of taking a monocation. The absorption spectroscopic study suggested an existence of the strong face-to-face interaction particularly in di-, tri-, and tetracationic state of the trimeric TTF derivatives.

Journal

  • Organic Letters

    Organic Letters 13 (12), 3122-3125, 2011-05-18

    American Chemical Society (ACS)

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