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Issue 27, 2016
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Synthesis of poly(allyl 2-ylidene-acetate) and subsequent post-polymerization modification via thiol–ene reaction

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Abstract

Poly(allyl 2-ylidene-acetate) (Mw = 125 300 g mol−1) was synthesized via rhodium mediated catalysis of allyl 2-diazoacetate and its polymerization kinetics and polymer characteristics are presented and discussed. This polymer represents the first functional polymethylene accessible by a thiol–ene click-chemistry post-polymerization modification. Thiol–ene reactions were conducted under UV-irradiation utilizing 2,2-dimethoxy-2-phenylacetophenone as a photo-initiator. Differences to other polymethylenes, such as the inherent ability of poly(allyl 2-ylidene-acetate) to self-crosslink, and polymer characteristics are discussed. The inherent ability to self-crosslink is further utilized to form stable thin films. Subsequent modification of the surface leads to different surface properties as proven by contact angle measurement.

Graphical abstract: Synthesis of poly(allyl 2-ylidene-acetate) and subsequent post-polymerization modification via thiol–ene reaction

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Supplementary files

Article information


Submitted
10 May 2016
Accepted
10 Jun 2016
First published
13 Jun 2016

Polym. Chem., 2016,7, 4525-4530
Article type
Paper

Synthesis of poly(allyl 2-ylidene-acetate) and subsequent post-polymerization modification via thiol–ene reaction

T. Krappitz, D. Brauer and P. Theato, Polym. Chem., 2016, 7, 4525
DOI: 10.1039/C6PY00818F

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