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Fluorinated Azobenzenes Switchable with Red Light.

Anna-Lena Leistner1, Susanne Kirchner1, Johannes Karcher1

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New fluorinated azobenzene photoswitches enable efficient E→Z photoisomerization with red light, even in water. This leads to self-assembled materials that change viscosity upon red light irradiation, ideal for in vivo applications.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Biomedical Engineering

Background:

  • Red/NIR light-activated molecular photoswitches are ideal for biological applications due to deep tissue penetration (therapeutic window).
  • Few such photoswitches are reported, and even fewer function in aqueous environments.

Purpose of the Study:

  • To develop novel photoswitches responsive to red light for biological applications.
  • To investigate the photoisomerization efficiency of fluorinated azobenzenes in aqueous conditions.
  • To create self-assembling materials with light-tunable properties.

Main Methods:

  • Synthesis of fluorinated azobenzenes conjugated with unsaturated substituents.
  • Investigation of E→Z photoisomerization efficiency using UV-Vis spectroscopy.
  • Incorporation of the photoswitch into a cyclic dipeptide for self-assembly.
  • Rheological studies of the supramolecular material under red light irradiation.

Main Results:

  • Fluorinated azobenzenes demonstrated efficient E→Z photoisomerization (>75% Z at 660nm) with red light.
  • The photoswitching effect was confirmed in both simple aldehyde conjugates and a complex cyclic dipeptide.
  • The cyclic dipeptide self-assembled into a supramolecular material that reversibly altered viscosity upon red light exposure under physiological conditions.

Conclusions:

  • Fluorinated azobenzenes are promising candidates for red light-activated photoswitches in aqueous media.
  • Self-assembled supramolecular materials with light-responsive viscosity can be designed using these photoswitches.
  • This work paves the way for novel photopharmacology agents and in vivo phototriggered materials.