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Anion-Responsive Fluorescent Supramolecular Gels.

Giacomo Picci1, Matthew T Mulvee2, Claudia Caltagirone1

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Summary
This summary is machine-generated.

Three novel fluorescent low-molecular-weight gelators (LMWGs) were synthesized. One LMWG, L1, exhibits anion-dependent gelation, with specific anions inhibiting or delaying gel formation.

Keywords:
DFT calculationsanion recognitionnoncovalent interactionsstimuli-responsive gelssupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Low-molecular-weight gelators (LMWGs) are crucial in supramolecular chemistry for self-assembly.
  • Fluorescent LMWGs offer potential in sensing and materials applications.
  • Designing LMWGs with tunable gelation properties is an active research area.

Purpose of the Study:

  • To synthesize and characterize novel bis-urea fluorescent LMWGs.
  • To investigate the gelation behavior of these LMWGs in various solvents.
  • To explore the influence of anions on the gelation process of a specific LMWG (L1).

Main Methods:

  • Synthesis of bis-urea compounds L1, L2, and L3.
  • Sol-gel studies to determine gelation properties in different solvents.
  • Anion titration experiments in solution.
  • Proton nuclear magnetic resonance (1H-NMR) titrations.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Three novel bis-urea fluorescent LMWGs (L1, L2, L3) were successfully synthesized.
  • LMWGs L2 and L3 formed gels in apolar solvents, while L1 gelled in a polar solvent mixture (DMSO/H2O).
  • Anion-dependent gelation was observed for L1: fluoride and benzoate inhibited gelation, while phosphate delayed it.
  • 1H-NMR and DFT studies revealed that benzoate anions disrupt the self-assembled structure of L1, inhibiting gel formation.

Conclusions:

  • Novel fluorescent bis-urea LMWGs were developed with distinct gelation behaviors.
  • L1 demonstrates anion-responsive gelation, highlighting its potential for anion sensing.
  • The mechanism of anion-induced gel disruption involves disruption of non-covalent interactions, as supported by computational studies.