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 1,3dipolar 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.Scheme 1 The concept of magnetically stimulated rDA reaction using IONPs. † Electronic supplementary information (ESI) available: Detailed experimental procedures and NMR spectra. See a Determined by 1 H NMR spectroscopy by comparing the peak areas of the CH-O groups of oxanorbornene at δ = 5.13-5.39 ppm and the methylene protons of the PEO in α of the triazole ring at δ = 4.52 ppm.
PaperPolymer ChemistryPolym. Chem. This journal is
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.