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Issue 10, 2006
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Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group

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Abstract

The new sugar-based gelators 1 and 2 were synthesized, and their gelation abilities were evaluated in organic solvents and in water. Compound 1 gelates both water and organic solvents whereas 2 gelates only organic solvents. Superstructural difference between hydrogel 1 and organogel 2 was investigated by CD, TEM, AFM, 1H NMR and XRD. Hydrogel 1 displays a well-developed helical ribbon structure with 20–150 nm diameter and a length of several hundred µm whereas organogel 2 shows a twisted fiber structure of diameter 20 nm. CD measurements of hydrogel 1 and organogel 2 indicate that hydrogel 1 maintains a well-ordered chiral structure whereas organogel 2 maintains a relatively disordered chiral structure. The 1H NMR and XRD results suggest that the hydrophobic interaction in hydrogel 1 are relatively weak, with a relatively small region interdigitated between lipophilic alkyl groups. In addition, upon irradiation at 254 nm wavelength, hydrogel 1 reveals a red coloration at 540 nm. These results indicate that the self-assembled hydrogel 1 was polymerized by UV-irradiation. The intensity of the CD spectrum of the polymerized hydrogel markedly decreased. This result indicates that upon polymerization the highly ordered chiral structure of hydrogel 1 changes to a disordered molecular packing structure.

Graphical abstract: Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group

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Publication details

The article was received on 15 Feb 2006, accepted on 20 Mar 2006 and first published on 18 Apr 2006


Article type: Paper
DOI: 10.1039/B602279K
Citation: Org. Biomol. Chem., 2006,4, 2033-2038

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    Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group

    J. H. Jung, J. A. Rim, W. S. Han, S. J. Lee, Y. J. Lee, E. J. Cho, J. S. Kim, Q. Ji and T. Shimizu, Org. Biomol. Chem., 2006, 4, 2033
    DOI: 10.1039/B602279K

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