Gradient Polymer Elution Chromatographic Analysis of α,ω-Dihydroxypolystyrene Synthesized via ATRP and Click Chemistry

Gao, Haifeng; Louche, Guillaume; Sumerlin, Brent S.; Jahed, Nazeem; Golas, Patricia L.; Matyjaszewski, Krzysztof

doi:10.1021/ma051566g

Cited by 149 publications

(115 citation statements)

References 48 publications

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“…[46] For example, the group of Matyjaszewski reported the prepartation of a,w-dihydroxy polystyrene by combination of ATRP and CuAAC. [47] In 2004, the group of Vincent first presented tris (2-dioctadecylaminoethyl) amine (C18 6 tren), a sterically crowded tripodal ligand. [48] The corresponding copper(I) complex [Cu(C18 6 tren)]Br does not have to be prepared in situ, but can be isolated and handled in air.…”

Section: Catalysts For Cuaac Reactionsmentioning

confidence: 99%

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

et al. 2012

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It is better to light a candle than to curse the dark. AbstractThe copper-catalyzed azide-alkyne cycloaddition for the synthesis of 1,4-disubstituted 1,2,3-triazoles (CuAAC) is a variant of Huisgen's 1,3-dipolar cycloaddition which disburdens the thermal reaction from its major drawbacks such as poor regioselectivity, long reaction times and harsh conditions. In contrast to the widely used "black box" reagent mixtures, a molecularly defined, highly active catalyst system for homogeneous CuAAC reactions has been developed in this PhD project. In dependence on the postulated stepwise mechanism, its most important structural feature is the presence of two copper(I) ions irreversibly bound in the same catalyst molecule.A highly modular and profitable synthesis for bistriazolium hexafluorophosphate salts as precursors for the ancillary ligand system was devised. In analogy to the CuAAC catalyst systems of general formula [(NHC) 2 Cu]PF 6 described in literature, novel dinuclear copper(I) complexes with a bistriazolylidene ligand backbone and 1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene (IPr) as sacrificial ligand were prepared.However, these complexes did not show the expected high catalytic activity, most probably due to the strong coordination of the IPr ligands. In consequence, another family of dinuclear copper(I) complexes with m-coordinated acetate as labile ligand was synthesized by reaction of the bistriazolium hexafluorophosphate ligand precursors with copper(I) acetate in the presence of a base.The broad applicability and high catalytic activity of one of these bistriazolylidene dicopper acetate complexes was confirmed by a series of gaschromatographically mo-

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Section: Catalysts For Cuaac Reactionsmentioning

confidence: 99%

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

et al. 2012

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“…By using a click-chemistry-ATRP combination and a bifunctional initiator, a,x-dihydroxypolystyrene was successfully prepared. [81] Using click chemistry, various functional groups (such as carboxyl, olefin, and amine) were attached to the ends of polymers prepared by ATRP, and biomolecules were further attached to the polymer chain ends. [82][83][84] When an unsaturated difunctional initiator was used, the resulting telechelic polymer was coupled with a crosslinker to yield degradable model networks (Fig.…”

Section: Role Of Click Chemistry In Multifunctional Polymer Designmentioning

confidence: 99%

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

2007

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The increasing need for materials with tightly controlled structures will continue to fuel the induction of synthetic organic concepts into materials science. One powerful example is the embracement of “click chemistry” by the materials science community. Because of their high selectivity, near‐perfect reliability, high yields, and exceptional tolerance towards a wide range of functional groups and reaction conditions click reactions have recently attracted increased attention, specifically for use in polymer synthesis as well as for the modification of surfaces and nanometer‐ and mesoscale structures. As outlined in this Review article, click chemistry, such as the CuI‐catalyzed Huisgen 1,3‐dipolar cycloaddition and the Diels–Alder reaction, presents a synthetic concept that lends itself superbly to the controlled preparation of multifunctional materials.

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“…此外, 一些研究工作者还将原子转移自由基聚合(ATRP) [11] 或者可逆加成-断裂链转移聚合(RAFT) [12] [18] , Cu(II)被包裹于聚环氧乙烷链中, 阻止 Cu(II)还原生成 Cu(I), 致使该催化体系在含有长链聚环氧乙烷的点击反应中效率较低. 直接使用 Cu(I)催化点击反应也被广泛用于聚合物的合成中 [19] . Figure 4 GPC traces of polymer 3, 6 and 7 .…”

Section: 而又具选择性的化学反应来实现碳杂原子连接unclassified

Synthesis of Perfluorocyclobutyl Aryl Ether-Containing ABA Triblock Copolymer via Click Chemistry

Li¹,

Li²

2013

Chin. J. Org. Chem.

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Because of the unusual polymerization mechanism and normal high polymerization temperature of trifluorovinyl aryl ether monomers, it is difficult to synthesize perfluorocyclobutyl aryl ether (PFCB)-containing block copolymer via sequential addition of monomers. Here a coupling reaction via click chemistry to prepare PFCB-containing ABA triblock copolymer is reported. An azide-ended PFCB polymer, which was firstly prepared by end-modification of methyl-ended PFCB polymer, was coupled with alkynyl-ended polyethylene glycol via the azide alkyne Huisgen cycloaddition.

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Gradient Polymer Elution Chromatographic Analysis of α,ω-Dihydroxypolystyrene Synthesized via ATRP and Click Chemistry

Cited by 149 publications

References 48 publications

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

Synthesis of Perfluorocyclobutyl Aryl Ether-Containing ABA Triblock Copolymer via Click Chemistry

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