Issue 11, 2017

Synthetic upcycling of polyacrylates through organocatalyzed post-polymerization modification

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2017,8, 7705-7709

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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