Click chemistry step growth polymerization of novel α-azide-ω-alkyne monomers

Binauld, Sandra; Damiron, Denis; Hamaide, Thierry; Pascault, Jean‐Pierre; Fleury, Étienne; Drockenmuller, Éric

doi:10.1039/b805164j

Cited by 86 publications

(78 citation statements)

References 17 publications

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“…[3][4][5] From the viewpoint of polymer synthesis, to say nothing of the polyaddition via click chemistry, [6][7][8][9][10][11] polymers possessing clickable pendant groups 12,13 and/or end-functionalities [14][15][16] have attracted researchers' attention, as such polymers can be used as 'building blocks' for syntheses of highly functionalized polymers, 17,18 construction of sophisticated topology, 19,20 and surface modification 21,22 .…”

Section: Introductionmentioning

confidence: 99%

Stereoregular poly(methyl methacrylate) with double-clickable ω-end: synthesis and click reaction

2015

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Isotactic and syndiotactic poly(methyl methacrylate)s with orthogonally double-clickable terminal ends, that is, α,β-unsaturated ester for Michael addition-type thiol-ene reaction and azide or alkynyl groups for azide-alkyne click reaction, were prepared via terminating reaction of stereospecific anionic polymerization with propargyl and 2-chloroethyl α-(chloromethyl)acrylates. The subsequent polymer modification via double click reaction proceeded quantitatively in one -pot system under ambient conditions. The facile and almost quantitative double-end-functionalization would open a new material design based on stereoregular PMMAs with controlled molecular weights.

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Section: Introductionmentioning

confidence: 99%

Stereoregular poly(methyl methacrylate) with double-clickable ω-end: synthesis and click reaction

2015

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“…Copper-catalyzed azide-alkyne cycloaddition (CuAAC) was selected for the step-growth chemistry because it has been shown to be an effective tool for macromolecular ligation. [84][85][86][87][88][89][90][91][92] In particular, Matyjaszewski and co-workers [93] and Drockenmuller and co-workers [94,95] demonstrated that step-growth CuAAC polymerizations proceed generally in high yields. This aspect was also verified in our study.…”

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confidence: 99%

Tailored Polymer Microstructures Prepared by Atom Transfer Radical Copolymerization of Styrene and N‐substituted Maleimides

Lutz¹,

Schmidt²,

Pfeifer³

2011

Macromol. Rapid Commun.

133

124

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In the present Feature Article, a kinetic strategy for controlling the microstructure of synthetic polymer chains prepared via a radical chain‐growth polymerization process is presented. This approach was recently developed in our laboratory and relies on the controlled kinetic addition of ultrareactive N‐substituted maleimides during the atom transfer radical polymerization of styrene. This method is experimentally straightforward and can be applied to a broad library of functional N‐substituted maleimides. Thus, this platform allows synthesis of unprecedented polymer materials such as 1D macromolecular arrays. The basic kinetic requirements, the experimental conditions, and the synthetic scope of this approach are discussed in details herein. magnified image

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“…An explanation of this effect based on the odd-evens reduction in crystallinity has been previously used in polyesters, where monomers from odd-chain length exhibit reduced enthalpies of melt and crystallization [37]. The density of triazole hydrogen bonding within a polymer has previously been demonstrated to be a factor influencing the glass transition temperature of polymers and dictating many thermal properties as well [38]. In the study by Binauld et al, monomers with equal carbon numbers were synthesized with both ester and ether linkages then polymerized into polytriazoles containing only ether linkages, polytriazoles with ester linkages only, and a copolymer consisting of both.…”

Section: Resultsmentioning

confidence: 99%

Vegetable Oil Derived Solvent, and Catalyst Free “Click Chemistry” Thermoplastic Polytriazoles

Floros

Leão

Narine

2014

BioMed Research International

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Azide-alkyne Huisgen “click” chemistry provides new synthetic routes for making thermoplastic polytriazole polymers—without solvent or catalyst. This method was used to polymerize three diester dialkyne monomers with a lipid derived 18 carbon diazide to produce a series of polymers (labelled C18C18, C18C9, and C18C4 based on monomer chain lengths) free of residual solvent and catalyst. Three diester dialkyne monomers were synthesized with ester chain lengths of 4, 9, and 18 carbons from renewable sources. Significant differences in thermal and mechanical properties were observed between C18C9 and the two other polymers. C18C9 presented a lower melting temperature, higher elongation at break, and reduced Young's modulus compared to C18C4 and C18C18. This was due to the “odd-even” effect induced by the number of carbon atoms in the monomers which resulted in orientation of the ester linkages of C18C9 in the same direction, thereby reducing hydrogen bonding. The thermoplastic polytriazoles presented are novel polymers derived from vegetable oil with favourable mechanical and thermal properties suitable for a large range of applications where no residual solvent or catalyst can be tolerated. Their added potential biocompatibility and biodegradability make them ideal for applications in the medical and pharmaceutical industries.

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Click chemistry step growth polymerization of novel α-azide-ω-alkyne monomers

Abstract: A novel step growth polymerization A-B strategy based on the click chemistry polyaddition of tailor-made alpha-azide-omega-alkyne low molar mass monomers was developed, leading to polytriazole (co)polymers with tunable structures and properties.

Cited by 86 publications

References 17 publications

Stereoregular poly(methyl methacrylate) with double-clickable ω-end: synthesis and click reaction

Stereoregular poly(methyl methacrylate) with double-clickable ω-end: synthesis and click reaction

Tailored Polymer Microstructures Prepared by Atom Transfer Radical Copolymerization of Styrene and N‐substituted Maleimides

Vegetable Oil Derived Solvent, and Catalyst Free “Click Chemistry” Thermoplastic Polytriazoles

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