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All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry
Author(s) -
Koschella Andreas,
Chien ChihYing,
Iwata Tadahisa,
Thonhofer Martin S.,
Wrodnigg Tanja M.,
Heinze Thomas
Publication year - 2020
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201900343
Subject(s) - click chemistry , chemistry , azide , alkyne , cellulose , polymer chemistry , monosaccharide , polymer , triazole , organic chemistry , sulfoxide , catalysis
Cellulose is functionalized with different monosaccharides by the azide–alkyne click chemistry approach. Either azide or alkyne moieties are attached to the cellulose backbone and allowed to react with sugar moieties bearing the opposite clickable groups. Between 16% and 100% of the reactive sites at the polymer can be functionalized with sugar molecules and a clear correlation between steric demand and DS Sugar is observed. The polymers remain soluble in aprotic dipolar media like dimethyl sulfoxide. Products with a sufficient hydrophilicity dissolve in water as well. FTIR‐ and NMR spectroscopy reveal the triazole formation and indicate an incomplete conversion of the reactive sites as usually observed in the field of click chemistry with polymers.