Diels–Alder “click” reactions: recent applications in polymer and material science

Taşdelen, Mehmet Atilla

doi:10.1039/c1py00041a

Cited by 508 publications

(365 citation statements)

References 268 publications

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“…During the course of development of azide-alkyne click reactions, the thiol-ene and Diels-Alder (DA) reactions have been identified to possess the "click" features [7][8][9][10][11][12][13]. Similar to the thiol-ene click reaction, the thiol-yne one could also be included into the catalogue of click reactions [14,15].…”

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confidence: 99%

Thiol-yne click polymerization

et al. 2013

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The research on using thiol-ene click reaction to synthesize sulfur-containing polymers with topological structures and advanced functional properties is a hot topic. However, the application of the thiol-yne reaction in the functional polymer preparation is limited and the thiol-yne click polymerization is to be further developed. In this review, we summarized recent research efforts on using thiol-yne click polymerization to synthesize polymers with topological structures. The sulfur-containing polymers were facilely prepared by photo-and thermo-initiated, amine-mediated, and transition-metal-catalyzed thiol-yne click polymerizations. These polymers are promising to be used as drug-delivery vehicles, high refractive index optical materials, photovoltaic materials, and biomaterials etc.thiol-yne click polymerization, radical mechanism, amine, rhodium complex, function Citation:

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confidence: 99%

Thiol-yne click polymerization

et al. 2013

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“…After successful discovery of click chemistry concept by Sharpless and Meldal, it is easy to perform polymer modification with high yield under mild conditions, such as rapid, stereospecific, orthogonal and no by-product coherent with the green chemistry [26]. Today, a series of reactions including Huisgen type Cu(I) catalyzed cycloaddition (CuAAC) [27,28], thiol-ene [29][30][31] and Diels-Alder [32] are recognized as well-known click chemistry reactions [33]. Modification of polymers with CuAAC click reaction is very general, robust and particularly simple compared to other click chemistry reactions [34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Polypropylene-based graft copolymers via CuAAC click chemistry

Açık¹,

Sey²,

Taşdelen³

2018

Express Polym. Lett.

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Abstract. Graft copolymers from commercial chlorinated polypropylene (PP-Cl) possessing either poly(ethylene glycol) (PEG) or poly(ɛ-caprolactone) (PCL) grafts are synthesized by copper (I)-catalyzed azide-alkyne cycloaddition 'click' reaction (CuAAC). For this purpose, azido-functional polypropylene is prepared by nucleophilic substitution of chlorine groups of PP-Cl with azidotrimethylsilane-tetrabutylammonium fluoride. Whereas, the clickable alkyne end-functional PEG and PCL are independently synthesized by esterification reaction of poly(ethylene glycol) methyl ether with 4-pentyonic acid at room temperature and ring-opening polymerization of ε-caprolactone using stannous octoate as catalyst and propargyl alcohol as initiator. Finally, the corresponding graft copolymers, PP-g-PEG and PP-g-PCL, with different surface properties were successfully synthesized by CuAAC 'click' reaction under mild condition. Spectral, chromatographic and thermal analyses at various stages prove the formation of desired polypropylene-based graft copolymers with well-defined properties. Furthermore, the water contact angle values of PP-Cl, PP-g-PEG and PP-g-PCL are found as 90±1°, 78±1.8° and 83±2.1°, respectively.

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“…In addition, modular ligation chemistry can be utilized to enhance the functionality and complexity of the individual building blocks with high functional group tolerance, [28] thereby enabling the precise design of macromolecular building blocks in afacile fashion, for example,b yc opper(I)-catalyzed azide-alkyne cycloadditions (CuAAc), [29] Diels-Alder reactions, [30] or thiol-X processes. [31] Thec ombination of reversible deactivation radical polymerization and modular ligations is ideal for the generation of polymeric building blocks for dynamic materials.…”

Section: Introduction 8351mentioning

confidence: 99%

Dynamic Macromolecular Material Design—The Versatility of Cyclodextrin‐Based Host–Guest Chemistry

2017

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Dynamic and adaptive materials are powerful constructs in macromolecular and polymer chemistry with a wide array of applications in drug delivery, bioactive systems, and self‐healing materials. Very often, dynamic materials are based on carefully tailored cyclodextrin host–guest interactions. The precise incorporation of these host and guest moieties into macromolecular building blocks allows the formation of complex macromolecular structures with predefined functions. Thus, dynamic materials with extraordinary adaptive property profiles—responsive to thermal, chemical, and photonic fields—become accessible. This Review explores the hierarchical formation of dynamic materials and complex macromolecular structures from the molecular via the macromolecular to the colloidal and macroscopic level, with a specific emphasis on the functionality and responsiveness of the assemblies, specifically in biological contexts.

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Diels–Alder “click” reactions: recent applications in polymer and material science

Cited by 508 publications

References 268 publications

Thiol-yne click polymerization

Thiol-yne click polymerization

Polypropylene-based graft copolymers via CuAAC click chemistry

Dynamic Macromolecular Material Design—The Versatility of Cyclodextrin‐Based Host–Guest Chemistry

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