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

Jong Hwa Jung, Jeong Ah Rim, Won Seok Han, Soo Jin Lee, Young Joo Lee, Eun Jin Cho, Jong Seung Kim, Qingmin Ji, Toshimi Shimizu

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43 Citations (Scopus)

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 m 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.

Original languageEnglish
Pages (from-to)2033-2038
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number10
DOIs
Publication statusPublished - 2006
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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  • Cite this

    Jung, J. H., Rim, J. A., Han, W. S., Lee, S. J., Lee, Y. J., Cho, E. J., Kim, J. S., Ji, Q., & Shimizu, T. (2006). Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group. Organic and Biomolecular Chemistry, 4(10), 2033-2038. https://doi.org/10.1039/b602279k