A supramolecular gel based on a glycosylated amino acid derivative with the properties of gel to crystal transition

Soft Matter. 2016 Jan 7;12(1):141-8. doi: 10.1039/c5sm02111a.

Abstract

Here we report the generation of a novel gelator from a glycosylated amino acid derivative, which contained three structural units, an aromatic residue, a carbohydrate moiety and a tert-butyl group in a single molecule. These structural units can promote the supramolecular self-assembly of this gelator in both aprotic and protic solvents via coordinated π-π stacking, multiple hydrogen binding and van der Waals interactions. More importantly, due to their non-equilibrium natures, the organogels formed in DCM, chloroform and ethanol can undergo gel to crystal transition in storage, driven by unbalanced gelator-gelator and solvent-gelator interactions. In this process, the gelators were firstly trapped in a kinetically favorable gel state, and then transferred into a more thermodynamically stable crystal state upon ageing, with the generation of microcrystals in different morphologies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspartic Acid / analogs & derivatives*
  • Chloroform / chemistry
  • Crystallization
  • Ethanol / chemistry
  • Fluorenes / chemistry
  • Gels / chemistry*
  • Glycosylation
  • Hydrogen Bonding
  • Oligopeptides / chemistry*

Substances

  • 9-fluorenylmethoxycarbonyl
  • Fluorenes
  • Gels
  • Oligopeptides
  • Aspartic Acid
  • Ethanol
  • Chloroform