[이은성 교수] Highly Stable 1,2-Dicarbonyl Radical Cations Derived from N-Heterocyclic Carbenes
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작성자 최고관리자 댓글 조회 작성일 21-06-23 09:35본문
Highly Stable 1,2-Dicarbonyl Radical Cations Derived from N-Heterocyclic Carbenes
Youngsuk Kim, Jung Eun Byeon, Gu Yoon Jeong, Seoung Su Kim, Hayoung Song, Eunsung Lee*
라디칼 물질들은 전자가 쌍을 이루지 않아 자성을 나타내는 특성이 있는데, 이들은 매우 불안정하여 다른 물질들과 쉽게 반응하기 때문에 매우 다루기 어려운 물질이다. 이 논문에서는 다이카보닐 구조의 유기 라디칼을 질소-헤테로고리 카벤을 이용하여 안정화하여 합성에 성공하였다. 이 다이카보닐 라디칼은 다른 라디칼 물질들과 달리 200도의 고온 및 산염기 수용액, 산화제, 환원제 등에서 매우 높은 안정성을 보였으며, 특히 KP buffer나 horse blood serum과 같은 조건에서도 안정성을 보여 생체 내에서 응용이 가능할 것으로 기대된다.
Stable organic radicals have been of great academic interest not only in the context of fundamental understanding of reactive intermediates but also because of their numerous applications as functional materials. Apart from the early examples of triphenylmethyl and TEMPO derivatives, reports on air- and water-stable organic radicals are scarce, and their development remains a challenge. Herein, we present the design and synthesis of a novel organic radical based on a 1,2-dicarbonyl scaffold supported by N-heterocyclic carbenes (NHCs). The presented radical cations exhibit remarkable stability toward various harsh conditions, such as the presence of reactive chemicals (reductants, oxidants, strong acids, and bases) or high temperatures, by far exceeding the stability of triphenylmethyl and TEMPO radicals. In addition, physiological conditions including aqueous buffer and blood serum are tolerated. The steric and electronic stabilization provided by the two NHC moieties enabled the successful design of the highly stable radical.
https://pubs.acs.org/doi/10.1021/jacs.1c00707
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