Issue 9, 2014

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.

Graphical abstract: Synthesis of novel benzimidazole-carbazole-N-glycosylamines and their self-assembly into nanofibers

Supplementary files

Article information

Article type
Paper
Submitted
20 Mar 2014
Accepted
19 Jun 2014
First published
24 Jun 2014

New J. Chem., 2014,38, 4371-4379

Author version available

Synthesis of novel benzimidazole-carbazole-N-glycosylamines and their self-assembly into nanofibers

M. K. Dhinakaran, K. Soundarajan and T. Mohan Das, New J. Chem., 2014, 38, 4371 DOI: 10.1039/C4NJ00415A

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