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Single-Wavelength Visible-Light-Induced Reversible Isomerization of Stiff-Stilbene under Dynamic Covalent Control

2025/03/31 by Indigo M. Bekaert, Maxime A. Siegler, Sander J. Wezenberg · 1 voice
Materials Science · Neuroscience · #Luminescence and Fluorescent Materials #Photochromic and Fluorescence Chemistry #Photoreceptor and optogenetics research

paper · pdf · doi:10.1021/acs.orglett.5c00707

openalex publication_date 2025/03/31 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/03

Abstract

High Resolution Image Download MS PowerPoint Slide Formylation of stiff-stilbene enables isomerization by visible instead of UV light, as is monitored by UV–vis and 1 H NMR spectroscopy. Further, it allows dynamic covalent imine formation, which gives rise to slightly blue-shifted absorbance. As a result, the irradiation wavelength that is used to promote E → Z isomerization for the formylated species, causes the opposite Z → E isomerization for the imine derivative. This feature can be used to produce either isomer with the same light source under control of imine formation and hydrolysis. Single crystal X-ray analysis and TD-DFT calculations provide structural and electronic insight.

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