Issue 16, 2015

Phosphonated furan-functionalized poly(ethylene oxide)s using orthogonal click chemistries: synthesis and Diels–Alder reactivity

Abstract

The synthesis and the reactivity in Diels–Alder and retro Diels–Alder (DA/rDA) reactions of a series of novel phosphonated furan-functionalized PEO monomethyl ethers were investigated. Dimethylphosphonate-terminated furan-functionalized PEO monomethyl ethers and their phosphonic acid-terminated derivatives have been successfully prepared by using a combination of click copper-catalyzed 1,3-dipolar cycloaddition and Kabachnik–Fields reactions. Influence of both the substitution pattern of the furan ring and the solvent onto the DA/rDA process were investigated. It was found that the 3-substituted furan is the more reactive and that water facilitates both the DA and the rDA reactions, while maintaining the polymeric structure intact. The results demonstrate the potential of such structures for dynamic covalent applications and controlled drug delivery systems such as thermoreversible linkage of biological entities onto metallic nanoparticles.

Graphical abstract: Phosphonated furan-functionalized poly(ethylene oxide)s using orthogonal click chemistries: synthesis and Diels–Alder reactivity

Supplementary files

Article information

Article type
Paper
Submitted
05 Feb 2015
Accepted
02 Mar 2015
First published
04 Mar 2015
This article is Open Access
Creative Commons BY license

Polym. Chem., 2015,6, 3024-3030

Author version available

Phosphonated furan-functionalized poly(ethylene oxide)s using orthogonal click chemistries: synthesis and Diels–Alder reactivity

T. T. T. N'Guyen, G. Contrel, V. Montembault, G. Dujardin and L. Fontaine, Polym. Chem., 2015, 6, 3024 DOI: 10.1039/C5PY00188A

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements