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Designer molecular probes for phosphonium ionic liquids.

Robert Byrne1, Simon Coleman, Simon Gallagher

  • 1CLARITY: Centre for Sensor Web Technologies, National Centre for Sensor Research, Dublin City University, Dublin 9, Ireland.

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Photochromic probes reveal complex structuring in phosphonium ionic liquids (ILs). Functional groups guide probes, influencing thermodynamic and kinetic parameters beyond classical solvent models.

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Area of Science:

  • Physical Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Ionic liquids (ILs) exhibit unique solvent properties due to structured nanoscale domains.
  • Understanding IL structuring is crucial for predicting and controlling their behavior in various applications.
  • Photochromic molecular probes offer a sensitive method to investigate local environments within ILs.

Purpose of the Study:

  • To investigate the structuring of phosphonium-based ionic liquids using photochromic spiropyran probes.
  • To correlate the functional groups of the probes with their location and interactions within the IL.
  • To determine how IL structuring affects thermodynamic, kinetic, and solvatochromic parameters.

Main Methods:

  • Utilized three spiropyran derivatives (BSP-1, BSP-2, BSP-3) with hydroxyl, carboxylic acid, and aliphatic functional groups, respectively.
  • Analyzed probe behavior in various phosphonium-based ionic liquids.
  • Measured thermodynamic, kinetic, and solvatochromic parameters, including activation energies and thermal relaxation rates.

Main Results:

  • Polar probes (BSP-1, BSP-2) showed negative entropies of activation and high activation energies, suggesting specific interactions with IL polar/charged regions.
  • Non-polar probe (BSP-3) exhibited positive entropies of activation, indicating localization in interfacial polar/non-polar regions.
  • Differences in relaxation rates and activation energies highlight the distinct microenvironments experienced by each probe.

Conclusions:

  • The functional groups of spiropyran probes effectively map the structured domains within phosphonium ionic liquids.
  • IL structuring leads to non-classical solvent behavior, influencing probe kinetics and thermodynamics.
  • Alkyl chain interactions in phosphonium ILs may lead to nano-cavity formation, impacting probe dynamics.