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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Stimuli-responsive self-assembled nanostructures are crucial for advanced functional materials.
  • Nonsymmetrical amphiphiles offer unique properties for supramolecular assembly.
  • Halogen (X)-bonding is an effective noncovalent interaction for molecular recognition and self-assembly.

Purpose of the Study:

  • To develop emissive supra-π-amphiphiles in water using X-bonding interactions.
  • To investigate the role of X-bonding in the formation and morphology of nanostructures.
  • To explore the stimuli-responsive disassembly of these self-assembled materials.

Main Methods:

  • Synthesis of pyridyl functionalized naphthalene monoimide (NMI-Py) as X-bond acceptor.
  • Synthesis of iodotetrafluorophenyl functionalized polyethylene glycol (PEG-I) and triethylene glycol (TEG-I) as X-bond donors.
  • Characterization of self-assembled nanostructures using SCXRD and DFT calculations.
  • Investigation of pH-responsive behavior through acid-triggered disassembly.

Main Results:

  • Successful construction of emissive supra-π-amphiphiles in water via X-bonding.
  • Defined nanostructures (fibers and vesicles) formed, dependent on X-bond donor chain length (PEG-I vs. TEG-I).
  • X-bonding was confirmed as essential for nanostructure formation, with control molecules failing to assemble.
  • Acid-triggered disassembly demonstrated pH responsiveness and thermal robustness of the nanostructures.

Conclusions:

  • A unique supramolecular strategy utilizing X-bonding enables the facile fabrication of luminescent supra-π-amphiphiles.
  • The self-assembly process is governed by X-bonding, orthogonal dipole-dipole interactions, and π-stacking.
  • This approach allows for tunable morphology and stimuli-responsive disassembly, offering a platform for smart materials.