Issue 30, 2022

Supramolecular self-associating amphiphiles: determination of molecular self-association properties and calculation of critical micelle concentration using a high-throughput, optical density based methodology

Abstract

Supramolecular self-associating amphiphiles are a class of amphiphilic salt, the anionic component of which is ‘frustrated’ in nature, meaning multiple hydrogen bonding modes can be accessed simultaneously. Here we derive critical micelle concentration values for four supramolecular self-associating amphiphiles using the standard pendant drop approach and present a new high-throughput, optical density measurement based methodology, to enable the estimation of critical micelle concentrations over multiple temperatures. In addition, we characterise the low-level hydrogen bonded self-association events in the solid state, through single crystal X-ray diffraction, and in polar organic DMSO-d6 solutions using a combination of 1H NMR techniques. Moving into aqueous ethanol solutions (EtOH/H2O or EtOH/D2O (1 : 19 v/v)), we also show these amphiphilic compounds to form higher-order self-associated species through a combination of 1H NMR, dynamic light scattering and zeta potential studies.

Graphical abstract: Supramolecular self-associating amphiphiles: determination of molecular self-association properties and calculation of critical micelle concentration using a high-throughput, optical density based methodology

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Paper
Submitted
10 1 2022
Accepted
04 2 2022
First published
11 2 2022
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2022,20, 5999-6006

Supramolecular self-associating amphiphiles: determination of molecular self-association properties and calculation of critical micelle concentration using a high-throughput, optical density based methodology

A. Rutkauskaite, L. J. White, K. L. F. Hilton, G. Picci, L. Croucher, C. Caltagirone and J. R. Hiscock, Org. Biomol. Chem., 2022, 20, 5999 DOI: 10.1039/D2OB00066K

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