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Issue 47, 2019
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Dewar lactone as a modular platform to a new class of substituted poly(acetylene)s

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Abstract

A variety of 3-substituted-4-halocyclobutenes originating from Dewar lactone (2-oxabicyclo[2.2.0]hex-5-en-3-one) were synthesized and polymerized using the Hoveyda–Grubbs 2nd generation catalyst. The polymerization reactions were found to proceed in a controlled manner, which provided a means to tune polymer molecular weight and to effect chain extensions. Treating the polymers with an organic base (e.g., triethylamine) facilitated elimination and afforded the corresponding substituted poly(acetylene)s which featured substituents on every four carbon atoms along the polymer backbone. The polymers were characterized using gel permeation chromatography and a variety of different spectroscopic techniques (i.e., NMR, FT-IR, UV-vis, and Raman). The physical, chemical, and electronic properties of the polymers were found to be dependent on the pendant substituents.

Graphical abstract: Dewar lactone as a modular platform to a new class of substituted poly(acetylene)s

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Article information


Submitted
26 Aug 2019
Accepted
30 Oct 2019
First published
07 Nov 2019

Polym. Chem., 2019,10, 6401-6412
Article type
Paper

Dewar lactone as a modular platform to a new class of substituted poly(acetylene)s

J. Seo, S. Y. Lee and C. W. Bielawski, Polym. Chem., 2019, 10, 6401
DOI: 10.1039/C9PY01282F

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