Solving the Loss of Orthogonality During the Polyaddition of α-Azide-ω-Alkyne Monomers Catalyzed by Cu(PPh3)3Br: Application to the Synthesis of High-Molar Mass Polytriazoles

被引：40

作者：

Binauld, Sandra ^{[1
]}

Fleury, Etienne ^{[1
]}

Drockenmuller, Eric ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, INSA Lyon, CNRS,UMR 5223, F-69622 Villeurbanne, France

来源：

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY | 2010年 / 48卷 / 11期

关键词：

1,3-dipolar cycloaddition catalysts; alkynes; azides; click chemistry; gel permeation chromatography (GPC); heteroatom-containing polymers; NMR; polyaddition; staudinger; step-growth polymerization; thermogravimetric analysis (TGA); STEP-GROWTH POLYMERIZATION; PEPTIDE-BASED POLYMERS; CLICK-CHEMISTRY; STAUDINGER REACTION; 1,3-DIPOLAR CYCLOADDITIONS; RADICAL POLYMERIZATION; TERMINAL ALKYNES; LINEAR-POLYMERS; EFFICIENT; FUNCTIONALIZATION;

D O I：

10.1002/pola.24018

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Polyaddition of an alpha-azide-omega-alkyne monomer by Cu(PPh3)(3)Br catalyzed 1,3-dipolar cycloaddition was thoroughly studied as a model system to investigate the orthogonality of this click chemistry process. Indeed, loss of chain-end functionality and occurrence of side reactions have a tremendous impact on the molar mass of polymers obtained by step growth polymerization. Particularly, SEC, H-1, and P-31 NMR experiments have highlighted the occurrence of a Staudinger side-reaction between azide chain-ends and PPh3 from the copper(I) catalyst that dramatically alters M-n of the resulting polytriazoles. A significant enhancement of M-n could be achieved by using an alternative catalyst and optimized experimental conditions, that is, dilution and reaction time. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 2470-2476, 2010

引用

页码：2470 / 2476

页数：7

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