The synthesis and ring-opening metathesis polymerization of glycomonomers

Weaver, Lucy G., Singh, Yogendra, Burn, Paul L. and Blanchfield, Joanne T. (2016) The synthesis and ring-opening metathesis polymerization of glycomonomers. RSC Advances, 6 37: 31256-31264. doi:10.1039/c5ra25732h


Author Weaver, Lucy G.
Singh, Yogendra
Burn, Paul L.
Blanchfield, Joanne T.
Title The synthesis and ring-opening metathesis polymerization of glycomonomers
Journal name RSC Advances   Check publisher's open access policy
ISSN 2046-2069
Publication date 2016
Sub-type Article (original research)
DOI 10.1039/c5ra25732h
Open Access Status Not Open Access
Volume 6
Issue 37
Start page 31256
End page 31264
Total pages 9
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2017
Language eng
Subject 1500 Chemical Engineering
1600 Chemistry
Formatted abstract
The synthesis of a series of short poly(norbornene)s displaying pendant disaccharides is reported. para-(Propargyloxy)benzyl moieties were attached to a norbornenyl group via an ester or amide linkage, giving two different pre-monomers. A set of protected β-(1→6)-linked glucosamine-based disaccharides, structurally similar to the bacterial biofilm constituent poly-N-acetylglucosamine (PNAG), were attached to the pre-monomers via a Huisgen 1,3-dipolar cycloaddition reaction to generate a series of 'glycomonomers'. In the presence of a Grubbs' 3rd generation catalyst, the glycomonomers displayed variable reactivities that were dependent on the type of linkage (ester or amide) between the norbornenyl and benzyl moieties. In general, the amide-linked glycomonomers polymerized at a much slower rate and had a comparatively lower degree of polymerization than the corresponding ester-linked constructs. All the materials displayed a relatively narrow molecular weight distribution (Đ = 1.2-1.5).
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
School of Chemistry and Molecular Biosciences
 
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