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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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Publication details

The article was received on 08 Jun 2017, accepted on 22 Sep 2017 and first published on 29 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC02574B
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    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, Advance Article , DOI: 10.1039/C7SC02574B

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