Click chemistry with polysaccherides

T. Liebert, C. Hänsch, T. Heinze

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180 Citations (Scopus)
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Abstract

The copper-catalyzed Huisgen reaction as a typical example of click chemistry was realized with the polysaccharide cellulose for the first time. The generality, selectivity, and the efficiency of click chemistry perfectly fit the requirements of polysaccharide modification, which is demonstrated by the introduction of triazole-spacer bound functional groups, i.e., carboxylic ester, thiophene, and aniline moieties. Azide moieties introduced into cellulose via the tosyl derivative were simply transferred with ethynyl compounds under Cu(I) catalysis and mild and easily applicable conditions. Hydrolytically stable cellulose derivatives soluble in organic solvents, e.g., DMSO or DMF with DS up to 0.9 are obtained. The triazole substituted cellulose derivatives were characterized by elemental analysis, FTIR, 1H NMR, and 13C NMR spectroscopies and show no impurities or substructures resulting from side reactions. © 2006 WILEY-VCH Verlag GmbH & Co. KGaA.
Original languageEnglish
Pages (from-to)208-213
JournalMacromolecular Rapid Communications
Volume27
Issue number3
DOIs
Publication statusPublished - 2006

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