Self-assembly of novel benzimidazole N-glycosylamines into nanofibers and nanospheres

Abstract

A novel class of benzimidazole based partially protected N-glycosylamine amphiphiles possessing different alkyl chains were synthesized in good yield. The identities of the synthesized N-glycosylamines were confirmed using ¹H and ¹³C NMR and the molecular mass of representative samples was confirmed using MALDI-TOF mass analysis. All the benzimidazole based N-glycosylamines were found to exist in β-anomeric form, which was confirmed by ¹H NMR analysis. Gelation studies showed that these compounds gelate both aromatic and aliphatic solvents, even at lower CGC (0.8%). The representative gel was studied using SEM, TEM and XRD techniques. The conversion of nanofibers in the gel state (CGC: 0.8%) into nanospheres was observed upon addition of Cu²⁺ ions.