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제125회 대한화학회 학술발표회 및 총회 Should a Mechanophore be Vulnerable? Mechanical Force-induced Cycloaddition of Intact Aziridines

등록일
2020년 2월 6일 09시 59분 48초
접수번호
0676
발표코드
POLY.P-25 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
온라인 PDF 제출
발표형식
포스터
발표분야
Polymer Chemistry
저자 및
공동저자
Sangmin Jung, Hyo Jae Yoon*
Department of Chemistry, Korea University, Korea
Mechanical force could allow for chemical reaction pathways that are inaccessible under traditional thermal and photochemical conditions. Upon exposure to a mechanical force, mechanophores undergo cleavage of covalent bond to facilitate desired mechanochemical reactions. Therefore, vulnerable chemical structures are considered necessary in mechanochemistry. As tradeoffs, conventional mechanophores are often isomerizable, hindering stereoselective mechanochemical reactions. This presentation exhibits that a smallest N-heterocycle, aziridine, can be a new mechanophore. Nonactivated aziridine is incorporated into the backbone of macromolecule generated by entropically driven ring-opening metathesis polymerization. Counterintuitively, mechanical force-induced cycloaddition of the embedded intact aziridine with a dipolarophile takes place. This reaction does not obey conventional reaction routes such as formation of ylide or diradical intermediates prior to the event of cycloaddition. Our work demonstrates that robust structures can be a good mechanophore.

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