title: Synthesis and characterization of maltose-based amphiphiles as supramolecular hydrogelators.
abstract: Low molecular mass amphiphilic glycolipids have been prepared by linking a maltose polar head and a hydrophobic linear chain either by amidation or copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. The liquid crystalline properties of these amphiphilic materials have been characterized. The influence of the chemical structure of these glycolipids on the gelation properties in water has also been studied. Glycolipids obtained by the click coupling of the two components give rise to stable hydrogels at room temperature. The fibrillar structure of supramolecular hydrogels obtained by the self-assembly of these gelators have been characterized by electron microscopy. Fibers showed some torsion, which could be related with a chiral supramolecular arrangement of amphiphiles, as confirmed by circular dichroism (CD). The sol-gel transition temperature was also determined by differential scanning calorimetry (DSC) and NMR.
authors: Instituto de Ciencia de Materiales de Aragón (ICMA), Universidad de Zaragoza-CSIC, Dpt. Química Orgánica, Facultad de Ciencias, Pedro Cerbuna 12, 50009, Zaragoza, Spain.
authors: María J
authors: MJ
authors: Clemente
authors: Juliette
authors: J
authors: Fitremann
authors: Monique
authors: M
authors: Mauzac
authors: José L
authors: JL
authors: Serrano
authors: Luis
authors: L
authors: Oriol
mesh_terms: D000480:Alkynes / Q000737:chemistry; D002152:Calorimetry, Differential Scanning; D002384:Catalysis; D002627:Chemistry, Physical; D002942:Circular Dichroism; D006017:Glycolipids / Q000737:chemistry*; D020100:Hydrogels / Q000032:analysis / Q000138:chemical synthesis*; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000737:chemistry*; D008855:Microscopy, Electron, Scanning; D015394:Molecular Structure; D044367:Phase Transition; D013501:Surface-Active Agents / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D000480:Alkynes; D006017:Glycolipids; D020100:Hydrogels; D013501:Surface-Active Agents; D014867:Water; D008320:Maltose