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

doi:10.1002/macp.201900343

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-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 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.

Original language	English
Article number	1900343
Journal	Macromolecular Chemistry and Physics
Volume	221
Issue number	1
DOIs	https://doi.org/10.1002/macp.201900343
Publication status	Published - 1 Jan 2020

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

Access to Document

10.1002/macp.201900343

Cite this

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title = "All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry",

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.",

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AU - Koschella, Andreas

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AU - Wrodnigg, Tanja M.

AU - Heinze, Thomas

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

Abstract

Keywords

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