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

Research output: Contribution to journalArticle

40 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 May 25
Externally publishedYes

Fingerprint

Hydrogel
sugars
Sugars
nuclear magnetic resonance
irradiation
gelation
Organic solvents
water
ribbons
polymerization
atomic force microscopy
color
transmission electron microscopy
fibers
Nuclear magnetic resonance
Irradiation
wavelengths
Water
interactions
Gelation

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

Cite this

Jung, J. H., Rim, J. A., Han, W. S., Lee, S. J., Lee, Y. J., Cho, E. J., ... 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

Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group. / Jung, Jong Hwa; Rim, Jeong Ah; Han, Won Seok; Lee, Soo Jin; Lee, Young Joo; Cho, Eun Jin; Kim, Jong Seung; Ji, Qingmin; Shimizu, Toshimi.

In: Organic and Biomolecular Chemistry, Vol. 4, No. 10, 25.05.2006, p. 2033-2038.

Research output: Contribution to journalArticle

Jung, Jong Hwa ; Rim, Jeong Ah ; Han, Won Seok ; Lee, Soo Jin ; Lee, Young Joo ; Cho, Eun Jin ; Kim, Jong Seung ; Ji, Qingmin ; Shimizu, Toshimi. / Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group. In: Organic and Biomolecular Chemistry. 2006 ; Vol. 4, No. 10. pp. 2033-2038.
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