Issue 11, 2024

Understanding the effects of targeted modifications on the 1 : 2 Choline And GEranate structure

Abstract

1 : 2 Choline-and-geranate (CAGE) is an ionic liquid (IL) widely studied for its biomedical applications. However, both its industrial-scale preparation and its long-term storage are problematic so finding more suitable candidates which retain its advantageous properties is crucial. As a first step towards this we have conducted a targeted modification study to understand the effects of specific functional groups on the properties of CAGE. 1 : 2 Choline-and-octanoate and 1 : 2 butyltrimethylammonium-and-octanoate were synthesised and their thermal and rheological properties examined in comparison to those of CAGE. Using differential scanning calorimetry and polarising microscopy, the model compound was found to be an isotropic liquid, while the analogues were room-temperature liquid-crystals which transition to isotropic liquids upon heating. Dynamic mechanical analysis showed that the thermal behaviour of the studied systems was even more complex, with the ILs also undergoing a thermally-activated relaxation process. Furthermore, we have used electron paramagnetic resonance (EPR) spectroscopy, along with a variety of spin probes with different functional groups, in order to understand the chemical environment experienced by solutes in each system. The EPR spectra indicate that the radicals experience two distinct environments (polar and nonpolar) in the liquid-crystalline phase, but only one average environment in the isotropic phase. The liquid-crystalline phase experiments also showed that the relative populations of the two domains depend on the nature of the solutes, with polar or strongly hydrogen-bonding solutes preferring the polar domain. For charged solutes, the EPR spectra showed line-broadening, suggesting that their ionic nature leads to complex, unresolved interactions.

Graphical abstract: Understanding the effects of targeted modifications on the 1 : 2 Choline And GEranate structure

Supplementary files

Article information

Article type
Paper
Submitted
30 Okt 2023
Accepted
21 Feb 2024
First published
23 Feb 2024
This article is Open Access
Creative Commons BY-NC license

Phys. Chem. Chem. Phys., 2024,26, 8858-8872

Understanding the effects of targeted modifications on the 1 : 2 Choline And GEranate structure

A. Dobre, S. Koutsoukos, F. Philippi, D. Rauber, C. W. M. Kay, O. Palumbo, M. M. Roessler and T. Welton, Phys. Chem. Chem. Phys., 2024, 26, 8858 DOI: 10.1039/D3CP05271K

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