All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry

Andreas Koschella, Chih Ying Chien, Tadahisa Iwata, Martin S. Thonhofer, Tanja M. Wrodnigg, Thomas Heinze

Research output: Contribution to journalArticleResearchpeer-review

Abstract

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 DSSugar 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.

Original languageEnglish
Article number1900343
JournalMacromolecular chemistry and physics
Volume221
Issue number1
DOIs
Publication statusPublished - 1 Jan 2020

Fingerprint

Cellulose derivatives
sugars
cellulose
Sugars
Polymers
chemistry
Cellulose
polymers
Bearings (structural)
monosaccharides
Triazoles
Alkynes
Azides
Dimethyl sulfoxide
Monosaccharides
Hydrophilicity
alkynes
Dimethyl Sulfoxide
Nuclear magnetic resonance spectroscopy
nuclear magnetic resonance

Keywords

  • 5-azido-5-deoxy aldoses
  • azide–alkyne click chemistry
  • solubility
  • structure–property relationships
  • sugar functionalized cellulose

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Fields of Expertise

  • Human- & Biotechnology

Cite this

All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry. / Koschella, Andreas; Chien, Chih Ying; Iwata, Tadahisa; Thonhofer, Martin S.; Wrodnigg, Tanja M.; Heinze, Thomas.

In: Macromolecular chemistry and physics, Vol. 221, No. 1, 1900343, 01.01.2020.

Research output: Contribution to journalArticleResearchpeer-review

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