Air- and heat-stable planar tri-p-quinodimethane with distinct biradical characteristics |
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Authors: | Zhu Xiaozhang Tsuji Hayato Nakabayashi Koji Ohkoshi Shin-ichi Nakamura Eiichi |
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Institution: | Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. |
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Abstract: | A heptacyclic carbocycle possessing three p-quinodimethane units conjugated in one plane has been synthesized and shown to exhibit distinct biradical characteristics. The molecule has a HOMO/LUMO band gap of ca. 1 eV and a S(0)-T(1) energy gap of 2.12 kcal/mol, and it absorbs and emits near-IR light at room temperature. It is air-stable under ambient light for several months and thermally stable up to 160 °C under nitrogen, and it undergoes reversible two-electron oxidation and reduction. The synthetic approach is such that a smaller and larger oligo-p-quinodimethane can be synthesized. |
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