Exploiting spatial isomerism to modulate the assembled phase and rheological response of compositionally identical sugar-based surfactants
(2025) In Chemical Science 16(9). p.4048-4056- 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... (More)
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.
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- author
- Poon, Jia Fei ; Cabezón, Alfonso ; Gulotta, Alessandro LU ; Mahmoudi, Najet ; Ulvenlund, Stefan LU ; Garcia-Fandiño, Rebeca and Sanchez-Fernandez, Adrian
- organization
- publishing date
- 2025-01-22
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Chemical Science
- volume
- 16
- issue
- 9
- pages
- 9 pages
- publisher
- Royal Society of Chemistry
- external identifiers
-
- pmid:39886440
- scopus:85216958430
- ISSN
- 2041-6520
- DOI
- 10.1039/d4sc08242g
- language
- English
- LU publication?
- yes
- additional info
- Publisher Copyright: © 2025 The Royal Society of Chemistry.
- id
- bb229a5f-521b-4ab5-90e8-00c66e9093be
- date added to LUP
- 2025-04-11 13:49:13
- date last changed
- 2025-05-09 14:47:54
@article{bb229a5f-521b-4ab5-90e8-00c66e9093be,
abstract = {{<p>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.</p>}},
author = {{Poon, Jia Fei and Cabezón, Alfonso and Gulotta, Alessandro and Mahmoudi, Najet and Ulvenlund, Stefan and Garcia-Fandiño, Rebeca and Sanchez-Fernandez, Adrian}},
issn = {{2041-6520}},
language = {{eng}},
month = {{01}},
number = {{9}},
pages = {{4048--4056}},
publisher = {{Royal Society of Chemistry}},
series = {{Chemical Science}},
title = {{Exploiting spatial isomerism to modulate the assembled phase and rheological response of compositionally identical sugar-based surfactants}},
url = {{http://dx.doi.org/10.1039/d4sc08242g}},
doi = {{10.1039/d4sc08242g}},
volume = {{16}},
year = {{2025}},
}