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Issue 12, 2017
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“Clickable PEG” via anionic copolymerization of ethylene oxide and glycidyl propargyl ether

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Abstract

A straight forward synthesis of poly(ethylene glycol) (PEG) with multiple alkyne groups distributed along the polymer chain is introduced. Direct access to clickable PEG is achieved by the monomer-activated anionic ring-opening copolymerization (AROP) of ethylene oxide (EO) with glycidyl propargyl ether (GPgE). Notably for successful polymerization no protection of the alkyne unit is required owing to the mild reaction conditions. Defined PEG-co-PGPgE and PGPgE (co)polymers with PDIs of 1.18–1.60 and molecular weights of Mn = 3000–9500 g mol−1 were prepared. In situ1H NMR kinetic studies revealed remarkably disparate reactivity ratios of rEO = 14.8 and rGPgE = 0.076, representing a pronounced compositional drift with EO rich segments close to the initiator and GPgE units near the chain terminus, i.e. copolymers with a steep monomer gradient. Copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) with mannopyranosyl azide leads to PEG-based glycopolymers and highlights the potential of alkyne-functional PEGs as a universal scaffold for a range of biomedical applications.

Graphical abstract: “Clickable PEG” via anionic copolymerization of ethylene oxide and glycidyl propargyl ether

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Supplementary files

Article information


Submitted
28 Jan 2017
Accepted
02 Mar 2017
First published
03 Mar 2017

Polym. Chem., 2017,8, 1882-1887
Article type
Communication

“Clickable PEG” via anionic copolymerization of ethylene oxide and glycidyl propargyl ether

J. Herzberger, D. Leibig, J. Langhanki, C. Moers, T. Opatz and H. Frey, Polym. Chem., 2017, 8, 1882
DOI: 10.1039/C7PY00173H

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