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Off-On Photo- and Redox-Triggered Anion Transport Using an Indole-Based Hydrogen Bond Switch.

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A novel indole-based switch enables controlled ion transport across membranes. Light or redox stimuli release caged protons, activating anion transport through hydrogen bonding.

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Area of Science:

  • Supramolecular Chemistry
  • Membrane Transport
  • Chemical Biology

Background:

  • Indole-based anionophores are crucial for transmembrane ion transport.
  • Controlling ion transport requires stimuli-responsive molecular switches.
  • Hydrogen bonding plays a key role in molecular recognition and transport.

Purpose of the Study:

  • To develop a stimulus-responsive indole-based hydrogen bonding switch.
  • To enable photo- and redox-activated transmembrane ion transport.
  • To investigate the mechanism of off-on activation of anion transport.

Main Methods:

  • Synthesis of an indole-based anionophore caged with o-nitrobenzyl and azobenzene groups.
  • Employing intramolecular hydrogen bonding to lock anion binding sites.
  • Utilizing light and redox stimuli for uncaging and activation of ion transport.
  • Monitoring anion transport across lipid bilayer membranes.

Main Results:

  • The caged anionophore exhibits suppressed anion binding and transport.
  • Photo- and redox-triggered uncaging releases the hydrogen bond donors.
  • The activated anionophore efficiently transports anions across lipid bilayers.
  • A six-membered intramolecular hydrogen bond formation was identified as the mechanism for inactivation.

Conclusions:

  • A photo- and redox-switchable indole-based hydrogen bonding system was successfully developed.
  • This system allows for precise control over transmembrane anion transport.
  • The findings open avenues for developing smart drug delivery systems and biosensors.