Chemical modifications of poly(vinyl chloride) to poly(vinyl azide) and “clicked” triazole bearing groups for application in metal cation extraction

Elamari, Hichem; Dardouri, Mokthar; Ncib, Sana; Meganem, Faouzi; Girard, Christian

doi:10.1016/j.reactfunctpolym.2016.01.016

Cited by 14 publications

(4 citation statements)

References 33 publications

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“…This may explain the access and/or stability of complexes formed between the metal the triazole nucleus. This effect has already been observed in the case of copper (II) and lead (II) in a work on PVC-supported triazolic amides [ 38 ].…”

Section: Resultssupporting

confidence: 58%

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Synthesis and Characterization of Polystyrene-Supported Piperazine-Substituted Triazoles by CuAAC and First Evaluation for Metal Ion Extraction

et al. 2016

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Abstract:The goal of this work was to synthesize substituted polystyrene for metal extraction and/or depollution by introduction of substituted piperazines as chelatants starting from Merrifield polymer. After transformation of Merrifield's resin in azidomethyl polystyrene, click-chemistry using copper (I)-catalyzed Huisgen's reaction (CuAAC) was performed to prepare different polymers grafted with 1,4-triazoles bearing the piperazines, containing an alkyne as the other counterpart in the CuAAC.The polymers were then first tested for their efficiency to remove various metal ions from neutral aqueous solutions (Fe 3+ , Ni 2+ , Cu 2+ , Zn 2+ and Pb 2+ ). The polymers were found to extract Ni 2+ and Zn 2+ with low efficiencies ď40%. For Fe 3+ and Cu 2+ , the average extraction was around 80%, and for Pb 2+ around 50%. The global selectivity for these polymers was found to be in the order of Fe 3+ ě Cu 2+ > Pb 2+ >> Ni 2+ > Zn 2+ .

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Section: Resultssupporting

confidence: 58%

“…In this series, we obtained far better extraction results than with our first series of triazolic polymers, based on poly(styrene) and poly(vinyl chloride) backbones, bearing propargyl amides and propiolic anilides [ 23 , 38 ].…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Characterization of Polystyrene-Supported Piperazine-Substituted Triazoles by CuAAC and First Evaluation for Metal Ion Extraction

et al. 2016

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“…With applications ranging from material science to medicinal chemistry it is not surprising that investigations connected with the CuAAC topic, or just making use of this technique, are appearing with impressive and increasingly high frequency in the literature. As shown in Figure 1, these advancements comprise long-standing topics and some incompletely settled aspects like, e.g., the reaction mechanism, as well as new trends and examples of use of CuAAC in unprecedented directions [6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)

Mandoli

2016

Molecules

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Abstract:The explosively-growing applications of the Cu-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between organic azides and alkynes (CuAAC) have stimulated an impressive number of reports, in the last years, focusing on recoverable variants of the homogeneous or quasi-homogeneous catalysts. Recent advances in the field are reviewed, with particular emphasis on systems immobilized onto polymeric organic or inorganic supports.

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“…The propargyl group was formed either on the side chain, on the anomeric center, or on the benzylidene protecting group of the crown cata lyst. The choice was also confirmed by the fact that PVC-bound triazoles, which were used for the extraction of metal ions, had already been prepared [25]. Furthermore, immobili zation of carbohydrates with click reaction has also been carried out [26].…”

Section: Resultsmentioning

confidence: 99%

Reusable Glucose-Based Crown Ethers Anchored to PVC

Varga,

Ujj,

Mátravölgyi

et al. 2023

Molecules

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The recovery and reuse of the enantioselective catalysts produced by tedious work are important not only from the perspective of green chemistry, but also from the point of view of productivity. Some of the carbohydrate-based crown ethers prepared in our research group were able to generate significant asymmetric induction in certain cases. However, they were not recoverable after the synthesis. Therefore, we modified the most effective structure with a propargyl group so that it can be attached to a polymer with an azide–alkyne reaction. It was investigated whether the position of the bonding affects the activity of the crown ethers, hence, the propargyl group was introduced either to the side chain, to the anomeric center or to the benzylidene protecting group. To anchor the macrocycles, low molecular weight PVC was modified with azide groups in 4% and 10%, respectively. It was found that glucose-based crown ether bearing the propargyl group on the benzylidene unit and grafted to PVC in 4% has the highest activity regarding the enantioselectivity (77% ee). The catalyst was recoverable in the Michael addition of diethyl acetamidomalonate to nitrostyrene and it could be reused five times without the loss of enantioselectivity.

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Chemical modifications of poly(vinyl chloride) to poly(vinyl azide) and “clicked” triazole bearing groups for application in metal cation extraction

Cited by 14 publications

References 33 publications

Synthesis and Characterization of Polystyrene-Supported Piperazine-Substituted Triazoles by CuAAC and First Evaluation for Metal Ion Extraction

Synthesis and Characterization of Polystyrene-Supported Piperazine-Substituted Triazoles by CuAAC and First Evaluation for Metal Ion Extraction

Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)

Reusable Glucose-Based Crown Ethers Anchored to PVC

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