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Orthogonal Click Postfunctionalization of Alternating Copolymers Prepared by Nitroxide-Mediated Polymerization

Orthogonal Click Postfunctionalization of Alternating Copolymers Prepared by Nitroxide-Mediated Polymerization

Matthias Tesch, Sergej Kudruk, Matthias Letzel, Armido Studer

Chemistry. 2017 May 2;23(25):5915-5919.

PMID: 28224673

Abstract:

Nitroxide-mediated polymerization (NMP) was applied to prepare alternating copolymers using 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) 1 and ((6-trimethylsilyl)-hex-5-yn-1-yl)vinyl ether (THVE) 2 as monomers. The alternating sequence of the resulting poly(HFIPA-alt-THVE) 3 was proved by using tandem mass spectrometry (MS/MS) and further supported by 1 H NMR spectroscopy. Alternating alkyne and activated ester moieties of copolymer 3 were further functionalized with organic azides and amines using sequential Cu-catalyzed azide-alkyne click (CuAAC) and amidation reactions, providing dually functionalized poly(acrylamide-alt-triazole) polymers 5. Water-soluble alternating poly(acrylic acid-alt-triazole) copolymers 9 were obtained by saponification of HFIP esters. 1 H and 19 F NMR spectroscopy, IR spectroscopy as well as gel permeation chromatography (GPC) were used to characterize the polymers before and after functionalization.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2160896	1,1,1,3,3,3-Hexafluoroisopropyl acrylate		2160-89-6	Price
LS775294	Poly(1,1,1,3,3,3-hexafluoroisopropyl acrylate)			Price

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