Preparation, Structure Determination, and Electrochemical Properties of 4,5‐Dialkylbenzo[1,2‐<i>d</i>:4,5‐<i>d’</i>]bis[1,2,3]triselenoles and Their Singlet and Triplet‐State Dications

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  • Takeshi Kimura
    Center for Instrumental Analysis Iwate University Morioka 020-8551 Japan
  • Tsukasa Nakahodo
    Department of Applied Chemistry Kindai University Higashi Osaka 577-8502 Japan
  • Eiichi Suzuki
    Department of Chemistry and Biological Sciences Faculty of Science and Engineering Iwate University Morioka 020-8551 Japan
  • Yoshiki Nakanishi
    Department of Physical Science and Materials Engineering Faculty of Science and Engineering Iwate University Morioka 020-8551 Japan
  • Yohji Misaki
    Department of Applied Chemistry Faculty of Engineering Ehime University Matsuyama 790-8577 Japan
  • Satoshi Ogawa
    Department of Chemistry and Biological Sciences Faculty of Science and Engineering Iwate University Morioka 020-8551 Japan

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<jats:title>Abstract</jats:title><jats:p>4,8‐Dialkylbenzo[1,2‐<jats:italic>d</jats:italic>:4,5‐<jats:italic>d’</jats:italic>]bis[1,2,3]triselenoles [alkyl=Et, Bu, and Oc (C<jats:sub>8</jats:sub>H<jats:sub>17</jats:sub>)] were first prepared and treated with concentrated sulfuric acid‐<jats:italic>d</jats:italic><jats:sub>2</jats:sub> to generate benzobistriselenole dications, which were determined by NMR spectroscopy. The oxidation of dioctylbenzobistriselenole with three equivalents of single‐electron oxidizing reagent (NOSbF<jats:sub>6</jats:sub>) produced the corresponding dication<jats:sup>.</jats:sup>2SbF<jats:sub>6</jats:sub><jats:sup>−</jats:sup>, and the salt was isolated into a stable form. The ESR spectra of the dications measured in concentrated sulfuric acid in the range of room temperature and −196 °C were observed as split peaks similar to that of solid state dication<jats:sup>.</jats:sup>2SbF<jats:sub>6</jats:sub><jats:sup>−</jats:sup>. Magnetic susceptibility of the dication<jats:sup>.</jats:sup>2SbF<jats:sub>6</jats:sub><jats:sup>−</jats:sup> was determined by a superconducting quantum interference device (SQUID) magnetometer, which showed the salt is diamagnetic. The optimized structures and the total energy of the singlet‐ and triplet‐state benzobistriselenole dications were calculated using the density functional theory (DFT) method at the B3LYP6‐311G**(d,p) level. The results revealed that the structures of the singlet‐ and triplet‐state dications calculated have a completely planar forms and the triplet‐state dication is slightly more stable than the singlet‐state one in acetonitrile using a polarizable continuum model (PCM).</jats:p>

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