Tailoring polyethers for efficient post-polymerization functionalization by cross metathesis

Morrison, S. D. , Liskamp, R. M.J. and Prunet, J. (2018) Tailoring polyethers for efficient post-polymerization functionalization by cross metathesis. Organic Letters, 20(8), pp. 2253-2256. (doi: 10.1021/acs.orglett.8b00595) (PMID:29600865)

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Olefin cross metathesis is reported for the first time to attach small molecules to a range of novel polyethers with a poly(ethylene glycol) backbone and pendent alkene groups, allowing for a loading of up to one compound per monomer unit. These polymers are tailored to prevent the occurrence of self metathesis (reaction of the polymer with itself) by varying the substitution on the pendent alkenes, thus steering their reactivity toward olefin cross metathesis. Efficient functionalization has been observed for a range of coupling partners as a proof of concept for the use of olefin metathesis to graft small and larger molecules to polyethers for drug delivery. This approach also paves the way for the use of olefin cross metathesis as an efficient method to functionalize a wide variety of polymers with pendent olefin groups.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert and Morrison, Mr Stephen and Prunet, Dr Joelle
Authors: Morrison, S. D., Liskamp, R. M.J., and Prunet, J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Publisher:American Chemical Society
ISSN (Online):1523-7052
Published Online:30 March 2018
Copyright Holders:Copyright © 2018 American Chemical Society
First Published:First published in Organic Letters 20(8): 2253-2256
Publisher Policy:Reproduced in accordance with the publisher copyright policy

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE
3005270Targeted Conjugate DrugsJoelle PrunetTenovus Scotland (TENOVUS)S17-04Chemistry