Synthesis of novel benzimidazole-carbazole-N-glycosylamines and their self-assembly into nanofibers†
Abstract
A novel class of alkyl-benzimidazole-carbazole based N-glycosylamines were synthesised in good yield. The identities of the synthesised compounds were confirmed using 1H and 13C NMR. The molecular mass of representative samples was also confirmed using MALDI-TOF and EI-mass analysis. From the 1H NMR analysis of N-glycosylamines the existence of the anomeric proton in β-configuration was identified and further supported by 1H–1H COSY and 2D-ROESY NMR analysis of the representative sample. All the N-glycosylamines were good gelators for aliphatic rather than aromatic solvents. Out of six gelators synthesised five were identified as supergelators, since they gelate at low CGC (<1%). The representative gel sample was characterized using SEM, HR-TEM, rheology and powder XRD. Microscopic analysis evidenced the self-assembly of N-glycosylamines into nanofibers.