Structures and Electronic Properties of Diisopropylaminoborane Substituted with Highly Electron-Rich π-Conjugated Systems and Their Oxidized States

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  • Kohei Yoshida
    Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 , Japan
  • Shuichi Suzuki
    Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 , Japan
  • Masatoshi Kozaki
    Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 , Japan
  • Keiji Okada
    Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 , Japan

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<jats:title>Abstract</jats:title> <jats:p>We have designed and synthesized three kinds of diisopropylaminoboranes substituted with two electron-donating π-conjugated systems, 2a: bis(phenothiazinyl) 2b: bis(N-phenyldihydrophenazinyl), and 2c: bis(phenoxazinyl) derivatives, and investigated their structures and electronic properties including those of oxidized species. The structural analyses of 2a–c and 2a–c•+ indicated that the π-electronic systems composed of boron and three nitrogen atoms showed unique structural deformation by one-electron-oxidation. The structures of the neutral compounds were almost C2-symmetrical, indicating that the two donor π-electronic systems are almost identical. In contrast, the radical cationic compounds were not C2-symmetrical structures because the charges of the radical cations were localized on one of the electron donors. In addition, the B–N bonds directly bound to the radical cations were elongated; also, perpendicular arrangements between the p-orbital of boron and π-conjugated orbitals of the radical cations were observed. We also succeeded in observing the triplet state of 2b2(•+), which was categorized as a heteroatom analogue of the trimethylenemethane (TMM) π-electronic system, by means of electron-spin resonance (ESR) spectroscopy.</jats:p>

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