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    Glycosyl squaramides, a new class of supramolecular gelators


    Ramos, Jessica and Arufe, Santiago and Martin, Harlei and Rooney, Denise and Elmes, Robert B. P. and Erxleben, Andrea and Moreira, Ramon and Velasco-Torrijos, Trinidad (2020) Glycosyl squaramides, a new class of supramolecular gelators. Soft Matter, 16 (34). pp. 7916-7926. ISSN 1744-683X

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    Abstract

    Glycosyl squaramides were synthesised and evaluated as low molecular weight gelators. Amphiphilic glycosyl squaramides 5 and 6, with a C-16 aliphatic chain, formed thermoreversible gels in polar organic solvents and 1 : 1 ethanol/water mixtures with high efficiency. Rheological analysis showed these gels achieve their structural stability 120 h after gelation and were robust, making them particularly suitable for biomedical applications. The interactions between solvent and gelator strongly influence SAFiN (Self-Assembled Fibrillar Network) formation, critical gelation concentration (CGC) and subsequent gel structure, as evidenced by SEM imaging of xerogels. Spectroscopic studies indicate that H-bonding is involved in the self-assembly of the glycosyl squaramides in organic solvents, while hydrophobic interactions are the major driving force for gel formation in the presence of water. The compounds described herein are the first reported examples of carbohydrate-squaramide conjugates capable of forming supramolecular gels.

    Item Type: Article
    Keywords: Glycosyl; squaramides; supramolecular gelators;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Faculty of Science and Engineering > Research Institutes > Human Health Institute
    Item ID: 16155
    Identification Number: https://doi.org/10.1039/D0SM01075H
    Depositing User: Dr. Denise Rooney
    Date Deposited: 21 Jun 2022 08:52
    Journal or Publication Title: Soft Matter
    Refereed: Yes
    URI:

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