Nishiuchi Tomohiko, Takahashi Kazuma, Makihara Yuta, Kubo Takashi
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ISC-OTRI), Osaka University, Osaka, Japan.
Beilstein J Org Chem. 2024 Sep 5;20:2254-2260. doi: 10.3762/bjoc.20.193. eCollection 2024.
The di(9-anthryl)methyl (DAntM) radical was synthesized and investigated to elucidate its optical, electrical properties, and reactivity. The generation of the DAntM radical was confirmed by its ESR spectrum, which showed two broad signals. The unpaired electron is primarily localized on the central sp carbon and slightly delocalized over the two anthryl moieties. Although the DAntM radical undergoes dimerization in solution, the radical still remains even at 190 K due to the bulky nature of the two anthryl groups. Interestingly, upon exposure to air, the purple color of the radical solution quickly fades to orange, resulting in decomposition to give 9-anthryl aldehyde and anthroxyl radical derivatives.
合成并研究了二（9-蒽基）甲基（DAntM）自由基，以阐明其光学、电学性质和反应活性。DAntM自由基的生成通过其电子顺磁共振（ESR）光谱得到证实，该光谱显示出两个宽信号。未成对电子主要定域在中心sp碳上，并在两个蒽基部分上略有离域。尽管DAntM自由基在溶液中会发生二聚化，但由于两个蒽基的庞大性质，即使在190 K时自由基仍然存在。有趣的是，暴露于空气中时，自由基溶液的紫色迅速褪色为橙色，导致分解生成9-蒽基醛和蒽氧基自由基衍生物。
