Issue 1, 2010
From the journal:

New Journal of Chemistry

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

Subbiah Nagarajan,a   Pawar Ravinder,b   Venkatesan Subramanianb  and  Thangamuthu Mohan Das*a  

* Corresponding authors

a Department of Organic Chemistry, University of Madras, Guindy Campus, India
E-mail: tmdas_72@yahoo.com
Fax: +91 44-22352494
Tel: +91 44-22202814

b Chemical Laboratory, Central Leather Research Institute (CSIR), Adyar, Chennai-600 020, India

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 π–π 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.

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

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Article information

DOI
https://doi.org/10.1039/B9NJ00400A
Article type
Paper
Submitted
12 Aug 2009
Accepted
29 Sep 2009
First published
05 Nov 2009

New J. Chem., 2010,34, 123-131

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

S. Nagarajan, P. Ravinder, V. Subramanian and T. Mohan Das, New J. Chem., 2010, 34, 123 DOI: 10.1039/B9NJ00400A

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