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Issue 48, 2015
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Solvent-free mechanochemical synthesis of a bicyclononyne tosylate: a fast route towards bioorthogonal clickable poly(2-oxazoline)s

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Abstract

The mechanochemical synthesis of a bicyclononyne tosylate (BCN-OTs) is presented. BCN-OTs is demonstrated to be a good initiator for the cationic ring-opening polymerization of 2-ethyl-2-oxazoline directly yielding BCN functional poly(2-ethyl-2-oxazoline) (PEtOx-BCN) with high chain end fidelity. Subsequent strain-promoted cycloadditions of the resulting PEtOx-BCN enable efficient additive-free conjugation reactions as demonstrated for the formation of a block copolymer and a PEtOx–protein conjugate.

Graphical abstract: Solvent-free mechanochemical synthesis of a bicyclononyne tosylate: a fast route towards bioorthogonal clickable poly(2-oxazoline)s

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Article information


Submitted
12 Aug 2015
Accepted
08 Oct 2015
First published
09 Oct 2015

Polym. Chem., 2015,6, 8354-8359
Article type
Paper

Solvent-free mechanochemical synthesis of a bicyclononyne tosylate: a fast route towards bioorthogonal clickable poly(2-oxazoline)s

M. Glassner, S. Maji, V. R. de la Rosa, N. Vanparijs, K. Ryskulova, B. G. De Geest and R. Hoogenboom, Polym. Chem., 2015, 6, 8354
DOI: 10.1039/C5PY01280E

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