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제117회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Mechanically-Coupled π-π Stacks: Double- and Triple-Decker Triazolobenzenes

등록일
2016년 2월 25일 14시 06분 04초
접수번호
1965
발표코드
ORGN.P-415 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
4월 22일 (금요일) 13:00~14:30
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
김도담, 이동환1,*
서울대학교 화학과, Korea
1서울대학교 화학부, Korea
As a prototypical non-covalent bond, π-π stacking interaction plays critical roles in protein folding, molecular recognition, and supramolecular assembly. Closely stacked π-conjugation can also function as conduits for charge carriers and excitons, which has engendered significant research interests in recent years. In order to maximize through-space interactions between π–π stacked aromatics, a precise control is needed for their spacing and relative orientations. We have designed and synthesized a series of “three-dimensional” (3-D) triazolobenzenes, in which naphthyl “struts” were strategically introduced to enforce intramolecular π–π contacts between the ring-fused heteropolycyclic core and aryl pendant groups. Solution 1H-NMR spectra of the doubly- and triply-stacked molecules revealed significantly upfield-shifted aromatic proton resonances that are characteristic of π–π stacking. X-ray crystallographic studies provided compelling structural evidence for the anticipated triple-decker aromatic arrangements, the conformational stability of which was investigated further by variable temperature (VT) 1H NMR, through-bond correlation spectroscopy (COSY), and through-space correlation spectroscopy (NOESY) studies. The functional relevance of such intimate π–π stacking was demonstrated by dramatic changes in light-emitting properties via through-space electronic coupling.

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