Issue 9, 2025

Exploiting spatial isomerism to modulate the assembled phase and rheological response of compositionally identical sugar-based surfactants

Abstract

For decades, extensive surfactant libraries have been developed to meet the requirements of downstream applications. However, achieving functional diversity has traditionally demanded a vast array of chemical motifs and synthetic pathways. Herein, a new approach for surfactant design based on structural isomerism is utilised to access a wide spectrum of functionalities. A library of C18-aliphatic maltosides was prepared through Koenigs–Knorr glycosylation, with their properties tuned through anomerism, stereoisomerism, regioisomerism, and the degree of tail unsaturation. Self-assembly of the amphiphiles gave rise to various morphologies, ranging from small micelles to large one-dimensional semiflexible assemblies, which were ultimately defined by the directionality of the supramolecular interactions imposed by the angular restraints of the isomeric centres. Remarkably, the microscopic phase determines the rheological behaviour of the system, which accesses Newtonian solutions, viscoelastic fluids, and gels with customised mechanical properties. The approach outlined in this study serves as a blueprint for the design of novel bioderived surfactants with diverse behaviours without altering the chemical composition of the surfactants, where the understanding of molecular interactions can potentially be used to predict and design the assembly and function of isomerically varied amphiphiles.

Graphical abstract: Exploiting spatial isomerism to modulate the assembled phase and rheological response of compositionally identical sugar-based surfactants

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Article information

Article type
Edge Article
Submitted
05 Dec 2024
Accepted
21 Jan 2025
First published
22 Jan 2025
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2025,16, 4048-4056

Exploiting spatial isomerism to modulate the assembled phase and rheological response of compositionally identical sugar-based surfactants

J. Poon, A. Cabezón, A. Gulotta, N. Mahmoudi, S. Ulvenlund, R. Garcia-Fandiño and A. Sanchez-Fernandez, Chem. Sci., 2025, 16, 4048 DOI: 10.1039/D4SC08242G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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