Protecting group/halogen effect of N-glycosylamines on the self assembly of organogelator

Abstract

A series of N-glycosylamine based organogelators were synthesised from three different 4,6-O-protected saccharides. All these compounds were characterized using different spectral techniques. The effect of substituents present in the N-glycosylamines on gelation was studied from NMR and computation. Among the eighteen different gelators studied, 3b, bearing fluorine as a substituent, was observed to gelate at very low concentrations (CGC: 1%). Further, it is revealed that dipole-dipole interactions play an important role in the case of N-glycosylamine-based gelators. The presence of p-p stacking and H-bonding, as inferred from the reported X-ray diffraction data, are responsible for the gelation. Various possible modes of interaction are identified from computational studies. The gelation properties of these compounds were studied with regard to their molecular structure by scanning electron microscopy, differential scanning calorimetry, FT-IR and NMR studies.

Recent Advances in C-Glycoside Chemistry: Application, Synthesis and Reactions

“…73 Figura 5. C-glicosídeos com propriedades físico-químicas e capacidade de formar gel Diversos tipos de gelificantes orgânicos de baixo peso molecular são descritos na literatura, 74 por apresentar habilidades específicas de gelificar uma grande variedade de líquidos. Dentre eles, podem ser encontrados derivados de monossacarídeos.…”

Regioselective facile one-pot Friedländer synthesis of sugar-based heterocyclic biomolecules

“…38 Even though a wide range of antibiotics are reported in the literature, 38 sugar-based antibiotics have greater impact on the scientific society. In a continuation of our ongoing research in the field of carbohydrate chemistry, [39][40][41][42][43][44] we herein report a facile one-pot regioselective synthesis of three different sugar-heterocyclic derivatives. , and 1-(2,3,4,6-tetra-O-acetyl-b-D-mannopyranosyl)-propan-2-ones (1g), were synthesized by Knoevenagel condensation of 2,4-pentadienone with 4,6-O-butylidene-D-glucopyranose, D-glucose, D-xylose, and D-galactose, respectively, followed by acetylation of the free hydroxyl group.…”

Pyrene Functionalized Luminescent Phenylalanine for Selective Detection of Copper (II) Ions in Aqueous Media

“…[29][30][31][32] The driving force for the formation of gel through selfassembly are non-covalent interactions such as electrostatic interaction, hydrophobic interaction, π-π interaction, hydrogen bonding interaction, and other supramolecular forces. 33,34 Fluorescent supramolecular gels derived from biologically relevant molecules are currently attracting many researchers worldwide because of their great application potential in several elds.…”