Issue 34, 2013
From the journal:

RSC Advances

Synthesis and characterization of thiourea- and urea-linked glycolipids as low-molecular-weight hydrogelators†

Manoharan Mathiselvam,*a   Duraikkannu Loganathan‡a  and  Babu Vargheseb  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India
E-mail: mathi24@gmail.com
Fax: 091-44-22574202
Tel: 091-44-22575221

b Sophisticated Analytical Instrumentation Facility, Indian Institute of Technology Madras, Chennai 600036, India

Abstract

Novel glycolipids with thiourea- and urea-linkers have been synthesized as low-molecular-weight gelators by reacting glycosyl aminoacetamides with alkyl isothiocyanates and isocyanates. The influence of the linker groups on their self-assembly properties has been studied. A gelation study of the obtained neoglycolipids in various solvents showed that they are good hydrogelators. Urea-linked glycolipids showed better hydrogelating ability as compared to thiourea linked glycolipids. The influence of sugar head group and alkyl chain length on the glycolipid’s self-assembly has also been studied. The fibrillar structures of the supramolecular hydrogels have been characterized by scanning electron microscopy (SEM). The thermal properties of the hydrogels formed by urea linked glycolipids have been studied by differential scanning calorimetry (DSC) and VT-NMR. Molecular packing has been studied by small angle (SAXS) and single crystal X-ray diffraction methods.

Graphical abstract: Synthesis and characterization of thiourea- and urea-linked glycolipids as low-molecular-weight hydrogelators

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Article information

DOI
https://doi.org/10.1039/C3RA42041H
Article type
Paper
Submitted
25 Apr 2013
Accepted
29 May 2013
First published
30 May 2013

RSC Adv., 2013,3, 14528-14542

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Synthesis and characterization of thiourea- and urea-linked glycolipids as low-molecular-weight hydrogelators

M. Mathiselvam, D. Loganathan and B. Varghese, RSC Adv., 2013, 3, 14528 DOI: 10.1039/C3RA42041H

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