Modular synthesis of block copolymers via cycloaddition of terminal azide and alkyne functionalized polymers

Opsteen, Joost A.; Hest, Jan C. M. van

doi:10.1039/b412930j

Cited by 515 publications

(398 citation statements)

References 17 publications

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“…[20] Later, the same group extended their work by synthesizing ABC triblock terpolymers, [21] in which they synthesized poly(methyl acrylate) (PMA)-b-PS-b-poly(tert-butyl acrylate) (PtBA) triblock terpolymers with the CuBr/tris[2-(dimethylamino)ethyl]amine (Me 6 TREN) catalytic system in N,N-dimethylformamide (DMF) at 50 8C in a modular (orthogonal) fashion by performing two sequential CuAAC click reactions of the polymeric precursors. All polymers were ATRP generated, whereby PMA-N 3 (M n = 7150 g mol polymers with PS containing terminal both anthracene and azide (anth-PS-N 3 ) moieties.…”

Section: Linear Terpolymersmentioning

confidence: 99%

Synthesis of Terpolymers by Click Reactions

Altintas

Tunca

2011

Chemistry An Asian Journal

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Well-defined polymeric structures were easily generated through living polymerization systems, in particular, living radical polymerizations. The polymeric precursors with orthogonal functionalities were subsequently clicked together with single or double (combinatorial) click reactions, such as the copper-catalyzed azide-alkyne cycloadditions (CuAAC) and Diels-Alder reactions, to create a wide variety of linear and nonlinear terpolymers.

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Section: Linear Terpolymersmentioning

confidence: 99%

Synthesis of Terpolymers by Click Reactions

Altintas

Tunca

2011

Chemistry An Asian Journal

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“…Exclusive chemoselectivity and perfect conversion yield are therefore highly required for the further modification reaction. To satisfy these criteria, we applied click chemistry for the further modification on Cel-N 3 [29][30][31][32][33].…”

Section: Cu + -Catalyzed [3 + 2]-cycloadditions Of the Alkyne-terminamentioning

confidence: 99%

Cellulose Chemistry Meets Click Chemistry: Syntheses and Properties of Cellulose-Based Glycoclusters with High Structural Homogeneity

et al. 2011

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-1,4-Glucans having oligosaccharide appendages (O-/N-linked -maltoside and O-/N-linked -lactoside) at 6C positions of all repeating units can be readily prepared from cellulose through a two step strategy composed of: (1) regio-selective and quantitative bromination/azidation to afford 6-azido-6-deoxycellulose; and (2) the subsequent Cu + -catalyzed coupling with oligosaccharides having terminal alkyne. The resultant cellulose derivatives showed improved water solubility in comparison to native cellulose; they, however, bound to carbohydrate-binding proteins in a rather non-specific manner. Molecular dynamics calculations revealed that these properties are attributable to rigid sheet-like structures of the cellulose derivatives and the subsequent exposure of their hydrophobic moieties to solvents.

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“…46 The Huisgen 1,3-dipolar cycloaddition between azides and alkynes 47 to yield triazoles meets the requirements for definition as a Click reaction 48 and has recently been utilized to functionalize surfaces, [49][50][51][52] polymers, 53,54 and sugars, [55][56][57] probe biological systems, [58][59][60][61][62] participate in multicomponent cascade reactions, 63,64 build libraries, 65,66 and synthesize analogues of vitamin D. 67 Because of toleration of a wide range of functionalities and high yielding reactions, the Huisgen 1,3-dipolar cycloaddition Click reaction between azides and alkynes is an obvious tool for building macromolecules, [68][69][70][71] and dendritic macromolecules, as demonstrated by the recent employment of this Click reaction to construct dendrimers convergently. 72 Both the convergent and divergent synthetic methodologies provide routes for the production of dendritic macromolecules; however, each has specific advantages.…”

Section: Introductionmentioning

confidence: 99%

Dendrimers Clicked Together Divergently

et al. 2005

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Dendrimers containing 1,4-triazole linkages between each generation were grown divergently via the Click chemistry inspired Huisgen 1,3-dipolar cycloaddition reaction in the presence of a Cu(I) catalyst. The monomeric unit (1-propargylbenzene-3,5-dimethanol) contained the alkyne functionality, while the core (1,2-bis(2-azidoethoxy)ethane) and growing dendrimers presented the azide groups necessary for this type of Click reaction. The first generation dendrimer was also functionalized with alkyne termini to demonstrate an alternative pathway allowed by this chemistry. Synthesis and characterization, with infrared (IR), 1 H and 13 C NMR spectroscopies, high-resolution mass spectrometry, gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA), are reported for these divergently grown dendrimers.

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Modular synthesis of block copolymers via cycloaddition of terminal azide and alkyne functionalized polymers

Abstract: Polymeric building blocks containing terminal azide and alkyne functionalities are prepared via atom transfer radical polymerization (ATRP) and used to modularly synthesize block copolymers via 1,3-dipolar cycloaddition reactions, which are quantitative according to SEC measurements.

Cited by 515 publications

References 17 publications

Synthesis of Terpolymers by Click Reactions

Synthesis of Terpolymers by Click Reactions

Cellulose Chemistry Meets Click Chemistry: Syntheses and Properties of Cellulose-Based Glycoclusters with High Structural Homogeneity

Dendrimers Clicked Together Divergently

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