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    Selective aliphatic/aromatic organogelation controlled by the side chain of serine amphiphiles


    Ramos, Jessica and Arufe, Santiago and O'Flaherty, Roisin and Rooney, A. Denise and Moreira, Ramon and Velasco-Torrijos, Trinidad (2016) Selective aliphatic/aromatic organogelation controlled by the side chain of serine amphiphiles. RSC Advances, 6. pp. 108093-108104. ISSN 2046-2069

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    Abstract

    The influence of two structural features of N-Fmoc-L-serine lipoamino acids on organogel formation were investigated. These were (i) the nature of the group on the serine side chain (hydroxyl compared to O-tert-butyl) and (ii) the length of the aliphatic chain (C-14 compared to C-18). O-tert-Butylated derivatives preferentially gelled saturated hydrocarbon solvents, while compounds with the hydroxyl group in the side chain promoted the highly unusual gelation of solely aromatic solvents. Extension of the chain length of the lipoamino acid (from C-14 to C-18) decreased the selectivity observed for the shorter chain homologues. Spectroscopic analyses of these systems indicated that H-bonds, aromatic π–π stacking and van der Waals interactions are involved in the gelation processes. Rheological characterization of the gels revealed the aromatic solvent gels to be more stable than their aliphatic counterparts. Scanning Electron Microscopy (SEM) imaging of the xerogels showed that the structure of gels formed in aromatic solvents differs significantly from those formed in aliphatic ones. The different self-assembly modes of the gelator molecules could be induced by steric effects which depend on the functional groups on the side chain. The organogels obtained were thermoresponsive, moldable and capable of self-healing. In addition, the lipoamino acids studied were phase selective gelators in biphasic mixtures of water/organic solvent and efficiently removed water soluble polluting dye rhodamine B from the aqueous phase.

    Item Type: Article
    Keywords: Selective aliphatic/aromatic organogelation; side chain; serine amphiphiles;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 10734
    Identification Number: https://doi.org/10.1039/C6RA21391J
    Depositing User: Dr. Trinidad Velasco-Torrijos
    Date Deposited: 23 Apr 2019 13:28
    Journal or Publication Title: RSC Advances
    Publisher: Royal Society of Chemistry
    Refereed: Yes
    Funders: John Hume Postgraduate Scholarship, Irish Research Council for Science (IRC)
    URI:

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