First example of “click” copper(i) catalyzed azide-alkyne cycloaddition in supercritical carbon dioxide: application to the functionalization of aliphatic polyesters

Grignard, Bruno; Schmeits, Stephanie; Riva, Raphaël; Detrembleur, Christophe; Lecomte, Philippe; Jérôme, Christine

doi:10.1039/b822924d

Cited by 19 publications

(10 citation statements)

References 36 publications

(38 reference statements)

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“…However, there are only four papers that use scCO 2 to carry out the CuAAC reactions. Therefore, the CuAAC reaction is yet far from being fully developed in scCO 2 . − …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂

et al. 2021

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A new sustainable green protocol for obtaining polyethylene glycol (PEG) conjugates, with a prototype molecule, which in this work was coumarin, by means of click chemistry is presented. The organic solvents commonly used for this type of reaction were replaced by supercritical carbon dioxide (scCO2). The synthesis and characterization of PEG-coumarin were successfully reported using FTIR, 1H NMR, and MALDI TOF. Subsequently, a preliminary study was carried out using the response surface methodology to examine the variables that most affect the use of scCO2 as a reaction medium. The main effects caused by these variables, individually and their binary interaction, have been estimated. The response surface methodology has been used in this work to screen variables using a factorial design 23. The p-values of temperature and pressure were 0.006 and 0.0117, being therefore the most significant variables of the response surface methodology study. Subsequently, a more intensive study has been carried out on the variables that have shown the greatest significant effect on reaction performance where an 82.32% synthesis success was achieved, which broadens the scope of the use of scCO2 as a reaction medium. The conjugated coumarin with mPEG-alkyne and coumarin were evaluated for their in vitro antioxidant activities by the DPPH radical scavenging assay and were found to exhibit substantial activities. The click product showed comparable or even better efficacy than the initial coumarin.

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“…However, there are only four papers that use scCO 2 to carry out the CuAAC reactions. Therefore, the CuAAC reaction is yet far from being fully developed in scCO 2 . − …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂

et al. 2021

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“…The “click” reaction is well known for its high efficiency in coupling azide and alkynyl functional groups and has been applied to the coupling of different types of polymers with varying properties . In this article, the “click” reaction of an alkyne functionalized polyimide with azide functionalized PDMS polymers were used.…”

Section: Resultsmentioning

confidence: 99%

Polyimide polydimethylsiloxane triblock copolymers for thin film composite gas separation membranes

Gurr

Scofield

Kim

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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This article demonstrates the successful fabrication of thin-film-composite (TFC) membranes containing welldefined soft-hard-soft triblock copolymers. Based on "hard" polyimide (PI) and "soft" polydimethylsiloxane (PDMS), these triblock copolymers (PDMS-b-PI-b-PDMS), were prepared via condensation polymerization, and end-group allylic functionalization to prepare the polyimide component and subsequent "click" coupling with the soft azido functionalized PDMS component. The selective layer consisted of pure PDMS-b-PI-b-PDMS copolymers which were cast onto a precast crosslinked-PDMS gutter layer which in turn was cast onto a porous polyacrylonitrile coated substrate. The TFC membranes' gas trans-port properties, primarily for the separation of carbon dioxide (CO 2 ) from nitrogen (N 2 ), were determined at 35 C and at a feed pressure of 2 atm. The TFC membranes showed improvements in gas permselectivity with increasing PDMS weight fraction. These results demonstrate the ability for glassy, hard polymer components to be coated onto otherwise incompatible surfaces of highly permeable soft TFC substrates through covalent coupling.

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“…To the best of our knowledge, CuAAC reactions performed in green scCO 2 are rarely reported (Scheme 1, previous works). [25][26][27] On the basis of our previous work, 27 the main work described in this paper shows a green protocol using copper wire as the recyclable catalyst for the CuAAC reaction in scCO 2 with a much easier work-up and purication (Scheme 1, this work).…”

Section: Introductionmentioning

confidence: 87%

“…In recently, considerable attentions have been focused on using supercritical carbon dioxide (scCO 2 ) as a reaction medium for organic reactions due to their attractive physical and toxicological properties. [25][26][27] On the basis of our previous work, 27 the main work described in this paper is showing a green protocol using copper wire as the recyclable catalyst for CuAAC reaction in scCO 2 with much easier work-up and purification (Scheme 1, this work). To the best of our knowledge, the CuAAC reactions performed in the green scCO 2 are rarely reported (Scheme 1, previous works).…”

Section: Introductionmentioning

confidence: 93%

Metallic copper wire: a simple, clear and reusable catalyst for the CuAAC reaction in supercritical carbon dioxide

Jiang

Zhang

et al. 2015

RSC Adv.

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An efficient protocol for the CuAAC reaction catalyzed by metallic copper wire for the synthesis of 1,4-disubstituted triazoles has been developed in supercritical carbon dioxide (scCO 2 ) at 50 ºC. The protocol could afford the corresponding products in excellent yield with a very easy work-up procedure. The metallic copper wire could be reused for more than 200 runs without decreasing the catalytic efficiency.

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First example of “click” copper(i) catalyzed azide-alkyne cycloaddition in supercritical carbon dioxide: application to the functionalization of aliphatic polyesters

Cited by 19 publications

References 36 publications

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂

Polyimide polydimethylsiloxane triblock copolymers for thin film composite gas separation membranes

Metallic copper wire: a simple, clear and reusable catalyst for the CuAAC reaction in supercritical carbon dioxide

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First example of “click” copper(i) catalyzed azide-alkyne cycloaddition in supercritical carbon dioxide: application to the functionalization of aliphatic polyesters

Cited by 19 publications

References 36 publications

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO2

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO2

Polyimide polydimethylsiloxane triblock copolymers for thin film composite gas separation membranes

Metallic copper wire: a simple, clear and reusable catalyst for the CuAAC reaction in supercritical carbon dioxide

Contact Info

Product

Resources

About

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂