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Issue 10, 2015

Synthesis of sequence-defined acrylate oligomers via photo-induced copper-mediated radical monomer insertions

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Abstract

Photo-induced copper-mediated radical polymerization is used to synthesize monodisperse sequence defined acrylate oligomers via consecutive single unit monomer insertion reactions and intermediate purification of the compounds by column chromatography or preparative recycling size exclusion chromatography. Monomer conversions are followed during reaction by means of infrared spectroscopy. When reaction conditions are chosen carefully and any residues from chlorinated solvents are avoided, 100% pure Br end capped sequence defined oligomers are obtained, demonstrating the convenience and power of photo-induced copper mediated radical insertion for establishing sequence control. Within this work, a library of sequence defined oligomers containing polar and apolar ester groups have been obtained, and for the first time, perfectly monodisperse acrylate pentamers became accessible from radical insertion reactions.

Graphical abstract: Synthesis of sequence-defined acrylate oligomers via photo-induced copper-mediated radical monomer insertions

Supplementary files

Article information


Submitted
07 Jun 2015
Accepted
29 Jun 2015
First published
03 Jul 2015

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

Chem. Sci., 2015,6, 5753-5761
Article type
Edge Article

Synthesis of sequence-defined acrylate oligomers via photo-induced copper-mediated radical monomer insertions

J. Vandenbergh, G. Reekmans, P. Adriaensens and T. Junkers, Chem. Sci., 2015, 6, 5753 DOI: 10.1039/C5SC02035B

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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