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Novel Biopolymer Structures Synthesized by Dendronization of 6‐Deoxy‐6‐aminopropargyl cellulose
Author(s) -
Pohl Matthias,
Heinze Thomas
Publication year - 2008
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200800452
Subject(s) - cellulose , biopolymer , amine gas treating , propargyl , chemistry , polymer chemistry , nucleophile , regioselectivity , nucleophilic substitution , organic chemistry , nuclear magnetic resonance spectroscopy , surface modification , catalysis , polymer
Propargyl cellulose with regioselective functionalization pattern was synthesized by nucleophilic displacement reaction of 6‐ O ‐toluenesulfonyl ester of cellulose (degree of substitution, DS 0.58) with propargyl amine. The novel 6‐deoxy‐6‐aminopropargyl cellulose provides an excellent starting material for the selective dendronization of cellulose at position 6 via the copper‐catalyzed Huisgen reaction yielding 6‐deoxy‐6‐amino‐(4‐methyl‐[1,2,3‐triazolo]‐1‐propyl‐polyamido amine) cellulose derivatives of first‐ (DS 0.33) and second (DS 0.25) generation, which are soluble in polar aprotic solvents. The novel biopolymer derivatives were characterized by elemental analysis, FT‐IR spectroscopy, and one‐ and two dimensional NMR spectroscopy, showing no side reactions (cross‐linking) or impurities and no conversion at the secondary positions.