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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Switchable Conformational Isomerization of an Overcrowded Tristricyclic Aromatic Ene
Tomohiko Nishiuchi1, Ryuoh Ito1, Erik Stratmann2
1Department of Chemistry, Graduate School of Science , Osaka University , 1-1 Machikaneyama , Toyonaka , Osaka 560-0043 , Japan.
Abstract:
We prepared a new overcrowded tristricyclic aromatic ene (TAE) and investigated its external stimuli-responsive behavior for the switching between a closed-shell folded form and an open-shell twisted form. Upon photoirradiation, the folded form transforms into the biradical twisted form, whereas by keeping the twisted form in the dark, the reverse reaction gradually occurs at room temperature. This switchable conformational change is analyzed by means of UV-vis and electron spin resonance spectroscopies, cyclic voltammetry, density functional theory calculations, and kinetic studies.
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