9,9′-Anthryl-anthroxyl radicals: strategic stabilization of highly reactive phenoxyl radicals

Tatsuya Aotake; Mitsuharu Suzuki; Naoki Aratani; Junpei Yuasa; Daiki Kuzuhara; Hironobu Hayashi; Haruyuki Nakano; Tsuyoshi Kawai; Jishan Wu; Hiroko Yamada

doi:10.1039/C4CC10104A

9,9′-Anthryl-anthroxyl radicals: strategic stabilization of highly reactive phenoxyl radicals†

Tatsuya Aotake,^a Mitsuharu Suzuki,^a Naoki Aratani,^a Junpei Yuasa,^a Daiki Kuzuhara,^a Hironobu Hayashi,^a Haruyuki Nakano,^b Tsuyoshi Kawai,^a Jishan Wu*^c and Hiroko Yamada*^ad

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* Corresponding authors

^a Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma 630-0192, Japan
E-mail: hyamada@ms.naist.jp

^b Department of Chemistry, Graduate School of Sciences, Kyushu University, Fukuoka 812-8581, Japan

^c National University of Singapore, 3 Science Drive 3, Singapore
E-mail: chmwuj@nus.edu.sg

^d CREST, Japan Science and Technology Agency (JST) 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan

Abstract

Stable 9,9′-anthryl-anthroxyl radicals were synthesized and isolated, and the structures were fully characterized by single crystal X-ray diffraction analysis and ESR measurement. The resonance structure and steric protection of the peripheral positions and the most reactive 9-position of anthracene prolong the half-life of the radical in solution to 11 days.

Chemical Communications

9,9′-Anthryl-anthroxyl radicals: strategic stabilization of highly reactive phenoxyl radicals†

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9,9′-Anthryl-anthroxyl radicals: strategic stabilization of highly reactive phenoxyl radicals

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