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제121회 대한화학회 학술발표회, 총회 및 기기전시회 Triazenyl Radicals Stabilized by N-Heterocyclic Carbenes

2018년 3월 12일 15시 21분 40초
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목 10시 : 47분
KCS - Oral Presentation for 2018 DOW Chemical Korea Award
저자 및
Jisu Back, Junbeom Park, Youngsuk Kim, Haneol Kang, Yonghwi Kim, Moon Jeong Park, Kimoon Kim, Eunsung Lee*
Department of Chemistry, Pohang University of Science and Technology, Korea
Notwithstanding the notable progress in the synthesis of N-heterocyclic carbene-stabilized radicals, aminyl radicals, supported by NHCs or otherwise, have been scarcely studied due to synthetic challenges. Triazenyl radical is a particular form of aminyl radical that contains three adjacent nitrogen atoms, and offers intriguing possibilities for unique reactivity and physical properties stemming from expected delocalization of the spin density over the NNN moiety and its conjugated substituents. Here, we report the synthesis and full characterization of the first NHC-stabilized triazenyl radicals, obtained by one-electron reduction of the corresponding triazenyl cations with potassium metal. These radicals reversibly oxidize back to the cations upon treatment with transition metal sources or electrophiles, and abstract H atom from xanthene to form a new N—H bond at the center nitrogen atom. Potential application of the redox couple between triazenyl cation and triazenyl radical was demonstrated as cathode active materials in lithium ion batteries.