Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols

Tran, Thi V.; Couture, Garret; H, Loi

doi:10.1039/c9dt00724e

Cited by 10 publications

(9 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…From previous literature on the CuAAC reaction, a specific phenomenon is that copper complexes are more susceptible to inhibition by forming molecular cages in some ligand environments. [34] Bu-NENA competes with the complexing ligand in the copper catalyst, inactivating the copper center and preventing the CuAAC reaction.…”

Section: Thermogravimetric (Tg) Analysismentioning

confidence: 99%

Curing Behaviors of Alkynyl-Terminated Copolyether with Glycidyl Azide Polymer in Energetic Plasticizers

Liu

Cong

et al. 2020

Polymers

View full text Add to dashboard Cite

Alkynyl-terminated polyethylene oxide−tetrahydrofuran (ATPET) and glycidyl azide polymer (GAP) could be linked through click-chemistry between the alkynyl and azide, and the product may serve a binder for solid propellants. The effects of the energetic plasticizers A3 [1:1 mixture of bis-(2,2-dinitropropy) acetal (BDNPA) and bis-(2,2-dinitropropyl) formal(BDNPN)] and Bu-NENA [N-butyl-N-(2nitroxyethyl) nitramine] on the curing reaction between ATPET and GAP have been studied. A diffusion-ordered nuclear magnetic resonance spectroscopy (DOSY-NMR) approach has been used to monitor the change in the diffusion coefficient of cross-linked polytriazole polyethylene oxide−tetrahydrofuran (PTPET). The change in the diffusion coefficient of PTPET with A3 plasticizer is significantly higher than that of PTPET with Bu-NENA. Viscosity analysis further highlighted the difference between A3 and Bu-NENA in the curing process—the curing curve of PTPET (A3) with time can be divided into two stages, with an inflection point being observed on the fourth day. For PTPET (Bu-NENA), in contrast, only one stage is seen. The above methods, together with gel permeation chromatography (GPC) analysis, revealed distinct effects of A3 and Bu-NENA on the curing process of PTPET. X-ray Photoelectron Spectroscopy (XPS) analysis showed that Bu-NENA has little effect on the valence oxidation of copper in the catalyst. Thermogravimetric (TG) analysis indicated that Bu-NENA helps to improve the thermal stability of the catalyst. After analysis of several possible factors by means of XPS, modeling with Material Studio and TG, the formation of molecular cages between Bu-NENA and copper is considered to be the reason for the above differences. In this article, GAP (Mn = 4000 g/mol) was used to replace GAP (Mn = 427 g/mol) to successfully synthesize the PTPET elastomer with Bu-NENA plasticizer. Mechanical data measured for the PTPET (Bu-NENA) sample included ε = 34.26 ± 2.98%, and σ = 0.198 ± 0.015 MPa.

show abstract

Section: Thermogravimetric (Tg) Analysismentioning

confidence: 99%

Curing Behaviors of Alkynyl-Terminated Copolyether with Glycidyl Azide Polymer in Energetic Plasticizers

Liu

Cong

et al. 2020

Polymers

View full text Add to dashboard Cite

show abstract

“…In the synthesis of 1,2,3-triazole derivatives, copper plays a prominent role in the formation of these compounds. On the premise of the work of Sharpless and Medal, special copper resources inclusive of Cu (I) 35 – 40 , MNP@PIL-Cu 41 , Cu-complicated 42 , Cu NPs 43 , and HMS-DP-Cu(II) 44 had been tested. Moreover, in current years, as a way to synthesize triazoles, many other strategies had been counseled 45 – 47 .…”

Section: Introductionmentioning

confidence: 99%

New Acetamidine Cu(II) Schiff base complex supported on magnetic nanoparticles pectin for the synthesis of triazoles using click chemistry

Siuki

Kargar

Bagherzade

2022

Sci Rep

View full text Add to dashboard Cite

In this project, the new catalyst copper defines as Fe3O4@Pectin@(CH2)3-Acetamide-Cu(II) was successfully manufactured and fully characterized by different techniques, including FT-IR, XRD, TEM, FESEM, EDX, VSM, TGA, and ICP analysis. All results showed that copper was successfully supported on the polymer‐coated magnetic nanoparticles. One of the most important properties of a catalyst is the ability to be prepared from simple materials such as pectin that’s a biopolymer that is widely found in nature. The catalytic activity of Fe3O4@Pectin@(CH2)3-Acetamide-Cu(II) was examined in a classical, one pot, and the three-component reaction of terminal alkynes, alkyl halides, and sodium azide in water and observed, proceeding smoothly and completed in good yields and high regioselectivity. The critical potential interests of the present method include high yields, recyclability of catalyst, easy workup, using an eco-friendly solvent, and the ability to sustain a variety of functional groups, which give economical as well as ecological rewards. The capability of the nanocomposite was compared with previous works, and the nanocomposite was found more efficient, economical, and reproducible. Also, the catalyst can be easily removed from the reaction solution using an external magnet and reused for five runs without reduction in catalyst activity.

show abstract

“…[ 34 ] To address this shortcoming, some recycled heterogeneous catalysts have been exploited accordingly. [ 35–41 ] They exhibit the advantages of high recycling frequency, easy separation, and better stability. [ 42–44 ] In this regard, Cu(I)‐based complexes have proven to be promising heterogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

Resorcin[4]arene‐based Cu(I) binuclear and mononuclear complexes as efficient catalysts for azide‐alkyne cycloaddition reactions

Qin

Liu

et al. 2021

Applied Organom Chemis

View full text Add to dashboard Cite

In this study, three fascinating resorcin[4]arene‐based Cu(I) complexes, named [CuCl (TPC4R)] (1), [CuBr (TPC4R)] (2), and [Cu2I2(TPC4R)] (3) were prepared by using a pyrimidine‐functionalized resorcin[4]arene ligand (TPC4R). In 1 and 2, two Cu(I) ions were linked by two TPC4R and two Cl− (or Br−) anions to form binuclear units. The adjacent units were extended into supramolecular layers through H bonds. In 3, two Cu(I) ions were connected by one TPC4R and two I− anions to form a mononuclear complex. The mononuclear units were connected by hydrogen bonds to produce a supramolecular chain. Significantly, 1 and 2 exhibit high efficiency and universality for azide‐alkyne cycloaddition reactions in the synthesis 1,2,3‐triazoles and β‐OH‐1,2,3‐triazoles. It has been found that the amount of catalyst, solvent type and reaction temperature have considerable influences on the activities of catalytic systems. The conversions of catalysts 1 and 2 could reach 99% for most of the selected substrates. It was found that after repeatedly used for 4 times, the catalytic activity of 1 did not decrease apparently.

show abstract

Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols

Abstract: The catalytic activity of dicopper azacryptands was evaluated in water and in the presence of biological thiols.

Cited by 10 publications

References 55 publications

Curing Behaviors of Alkynyl-Terminated Copolyether with Glycidyl Azide Polymer in Energetic Plasticizers

Curing Behaviors of Alkynyl-Terminated Copolyether with Glycidyl Azide Polymer in Energetic Plasticizers

New Acetamidine Cu(II) Schiff base complex supported on magnetic nanoparticles pectin for the synthesis of triazoles using click chemistry

Resorcin[4]arene‐based Cu(I) binuclear and mononuclear complexes as efficient catalysts for azide‐alkyne cycloaddition reactions

Contact Info

Product

Resources

About