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Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Creating water-soluble synthetic hosts with responsive cavities is difficult.
  • Such hosts are valuable for self-assembly, molecular machines, and biomedical applications.

Purpose of the Study:

  • To design and synthesize water-soluble naphthotubes with a pH-responsive cavity.
  • To investigate the pH-dependent guest binding properties and selectivity.

Main Methods:

  • Synthesis of water-soluble naphthotubes featuring inward-directing secondary amine groups.
  • pH-titration studies to characterize cavity changes.
  • Guest binding experiments in aqueous solutions to determine selectivity.

Main Results:

  • The naphthotubes exhibit a pH-responsive endo-functionalized cavity due to protonation/deprotonation of amine groups.
  • The hosts display distinct cavity features and drastically different guest binding preferences and selectivity at different pH values.
  • Binding differences are attributed to charge repulsion, hydrogen bonding, and hydrophobic effects.
  • Guest binding in a ternary mixture can be switched by adjusting the solution's pH.

Conclusions:

  • The developed pH-responsive naphthotubes offer a novel platform for stimuli-responsive supramolecular systems.
  • These hosts demonstrate potential for constructing smart self-assembly systems and water-soluble molecular machines.