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Acid-Responsive Inks via Shuttling in a Pseudorotaxane Complex.

Yihan Shi1, Robert Plavan1, Miguel A Soto1

  • 1Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.

Chempluschem
|August 21, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a pH-responsive molecular shuttle using a guest molecule and a cationic host. This system exhibits a stable color change from green to orange, enabling potential applications in information encryption.

Keywords:
cellulose nanocrystalshost‐guest systemsmolecular recognitionsupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Pseudorotaxanes are host-guest complexes featuring a guest molecule threaded through a macrocyclic host via noncovalent interactions.
  • These complexes can function as molecular shuttles, with the host dynamically moving between recognition sites on the guest in response to external stimuli.
  • Stimulus-responsive pseudorotaxanes offer tunable properties, including color and solubility, making them valuable for advanced materials.

Purpose of the Study:

  • To synthesize a novel guest molecule with distinct recognition sites for controlled host shuttling.
  • To investigate the stimulus-responsive behavior of a pseudorotaxane complex formed between the synthesized guest and a cationic host.
  • To explore the potential of this system in information encryption applications.

Main Methods:

  • Synthesis of a guest molecule (Gc) incorporating a 1,4-dialkoxyphenylene and a pH-sensitive 1,5-diaminonaphthalene recognition site.
  • Formation of a pseudorotaxane complex (Gc⊂CBPQT⁴⁺) with cyclobis(paraquat-p-phenylene) (CBPQT⁴⁺) host.
  • Monitoring color changes in solution upon pH-induced protonation/deprotonation of the guest molecule.
  • Incorporation of the complex into cellulose nanocrystal films for material-based applications.

Main Results:

  • The Gc⊂CBPQT⁴⁺ complex exhibited a distinct color change from green (neutral guest) to light orange (protonated guest) due to host shuttling.
  • The observed color-switching behavior was stable across multiple protonation-deprotonation cycles.
  • The pseudorotaxane complex could be disassembled, allowing for the recovery of the guest and host components.
  • Cellulose nanocrystal films containing the complex demonstrated reversible green-to-orange color changes.

Conclusions:

  • A novel pH-responsive pseudorotaxane molecular shuttle was successfully synthesized and characterized.
  • The system exhibits robust and reversible color-switching properties, driven by host shuttling in response to pH changes.
  • The demonstrated color-change capability in both solution and solid-state (cellulose nanocrystal films) highlights its potential for information encryption and smart material development.