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

Indigo M Bekaert1, Maxime A Siegler2, Sander J Wezenberg1

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|March 31, 2025
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Summary
This summary is machine-generated.

Formylation of stiff-stilbene allows visible light isomerization and dynamic imine formation. This enables reversible E/Z isomerization control using a single light source, offering novel applications in molecular switching.

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Area of Science:

  • Photochemistry
  • Organic Synthesis
  • Supramolecular Chemistry

Background:

  • Stiff-stilbene derivatives are photochromic molecules with potential applications in molecular switches.
  • Traditional stilbene isomerization often requires UV light, limiting practical applications.
  • Controlling isomerization and developing stimuli-responsive systems remains a key challenge.

Purpose of the Study:

  • To investigate the effect of formylation on the photoisomerization properties of stiff-stilbene.
  • To explore the potential of formylated stiff-stilbene in dynamic covalent chemistry for light-controlled isomer switching.
  • To provide structural and electronic insights into the observed phenomena.

Main Methods:

  • Synthesis of formylated stiff-stilbene derivatives.
  • Photoisomerization studies monitored by UV-vis spectroscopy.
  • Nuclear Magnetic Resonance (1H NMR) spectroscopy for structural analysis.
  • Single crystal X-ray diffraction for structural elucidation.
  • Time-Dependent Density Functional Theory (TD-DFT) calculations for electronic structure analysis.

Main Results:

  • Formylation shifted the photoisomerization of stiff-stilbene from UV to visible light.
  • Introduction of an imine linkage enabled dynamic covalent chemistry and light-responsive absorbance changes.
  • The same visible light wavelength induced opposite isomerization (E → Z and Z → E) in the formylated and imine derivatives.
  • Reversible isomer control was achieved by manipulating imine formation and hydrolysis.

Conclusions:

  • Formylated stiff-stilbene offers a pathway for visible-light-driven photoisomerization.
  • Dynamic imine formation provides a mechanism for light-controlled molecular switching.
  • The system demonstrates potential for developing advanced molecular devices and responsive materials.