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Issue 11, 2017
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Synthetic upcycling of polyacrylates through organocatalyzed post-polymerization modification

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Abstract

The direct transformation of commercially available commodity polyacrylates into value-added materials was achieved. We demonstrate how 1,5,7-triazabicyclo[4.4.0]dec-5-ene, serving as a nucleophilic catalyst, can be used to catalyze acyl substitution reactions of acrylic polymers in the presence of alcohol and amine nucleophiles. Furthermore, we found that organocatalytic transesterification exhibits high selectivity towards sterically unhindered esters, thus providing a new route towards site-selective acyl substitution of macromolecular materials. Combining this methodology with reversible-deactivation radical polymerization (RDRP) techniques such as reversible addition–fragmentation chain-transfer (RAFT) polymerization allowed for the precise functionalization of sterically-differentiated acrylic copolymers and polymeric chain ends. We envision this approach to expedite functional polymer synthesis and provide access to functional macromolecules prepared from inexpensive, hydrolytically-stable polymeric precursors.

Graphical abstract: Synthetic upcycling of polyacrylates through organocatalyzed post-polymerization modification

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Supplementary files

Article information


Submitted
08 Jun 2017
Accepted
22 Sep 2017
First published
29 Sep 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 7705-7709
Article type
Edge Article

Synthetic upcycling of polyacrylates through organocatalyzed post-polymerization modification

C. P. Easterling, T. Kubo, Zachary M. Orr, G. E. Fanucci and B. S. Sumerlin, Chem. Sci., 2017, 8, 7705
DOI: 10.1039/C7SC02574B

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