Synthesis, Structures, and Electronic Properties of 2,7-Anthrylene-Based Azacyclophanes Bearing <i>o</i>-, <i>m</i>-, and <i>p</i>-Phenylenediamine Linkers

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  • Tetsuo Iwanaga
    Department of Chemistry, Faculty of Science, Okayama University of Science, 1−1 Ridaicho, Kita-ku, Okayama 700-0005, Japan
  • Takashi Komori
    Department of Chemistry, Faculty of Science, Okayama University of Science, 1−1 Ridaicho, Kita-ku, Okayama 700-0005, Japan
  • Hiroki Sato
    Department of Chemistry, Faculty of Science, Okayama University of Science, 1−1 Ridaicho, Kita-ku, Okayama 700-0005, Japan
  • Shuichi Suzuki
    Department of Chemistry, Graduate School of Engineering Science, Osaka University, Machikaneyama, Toyonaka, Osaka 560-8531, Japan
  • Tomokazu Yamauchi
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan
  • Yohji Misaki
    Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan
  • Hiroyasu Sato
    X-ray Research Laboratory, Rigaku Corporation, 3−9−12 Matsubaracho, Akishima, Tokyo 196-8666, Japan
  • Shinji Toyota
    Department of Chemistry, School of Science, Tokyo Institute of Technology, 2−12−1 Ookayama, Meguro-ku, Tokyo 152−8551, Japan

説明

A series of novel azacyclophanes consisting of 2,7-anthrylene and phenylene units were designed and synthesized by the Buchwald-Hartwig coupling reaction to investigate their unique electronic properties in multiple oxidized states. Cyclic voltammetry showed that the p-phenylene derivative exhibited three reversible oxidation waves, whereas the o- and m-phenylene derivatives showed two quasi-reversible oxidation waves due to the complicated intramolecular interaction between the oxidized units and neutral units. Moreover, the absorption spectra of the p-phenylene derivative in different oxidation states showed absorption bands at 865 and 1025 nm, which were attributed to intramolecular charge-transfer interactions. The photophysical and electrochemical properties of the p-phenylene analog were also compared with those of the o- and m-phenylene derivatives based on theoretical calculations for further evaluation of the intramolecular electronic interactions.

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