ChemInform Abstract: [CuBr(PPh<sub>3</sub>)<sub>3</sub>] for Azide—Alkyne Cycloaddition Reactions under Strict Click Conditions.

Lal, Steven; Díez‐González, Silvia

doi:10.1002/chin.201127140

Cited by 5 publications

(5 citation statements)

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“…Functionalization of nanoparticles was carried out via copper(I)-catalyzed azide−alkyne cycloaddition reaction (CuAAC) between Si−Y or Ho−Y and the appropriate composition of PEGs using (PPh 3 ) 3 CuBr as catalyst. 29,30 For example, the particles bearing both fluorescein and polyarginine (Si-PEG-Flu-Arg) were prepared by mixing a certain amount of Si−Y with the same total amount of PEGs, of which 5 wt % consisted of PEG-Flu, 10 wt % of PEG-Arg, and the remaining 85 wt % of PEG-OMe (Scheme 2). When doing this, it was approximated that all PEGs had the same average molecular weight.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Fate of Organic Functionalities Conjugated to Theranostic Nanoparticles upon Their Activation

et al. 2015

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Neutron activation is widely applied for the preparation of radioactive isotopes to be used in imaging and/or therapy. The type of diagnostic/therapeutic agents varies from small chelates coordinating radioactive metal ions to complex nanoparticulate systems. Design of these agents often relies on conjugation of certain organic functionalities that determine their pharmacokinetics, biodistribution, targeting, and cell-penetrating abilities, or simply on tagging them with an optical label. The conjugation chemistry at the surface of nanoparticles and their final purification often require laborious procedures that become even more troublesome when radioactive materials are involved. This study represents a thorough investigation on the effects of neutron activation on the organic moieties of functionalized nanoparticles, with special focus on (166)Ho2O3 particles conjugated with PEG-fluorescein and PEG-polyarginine motives. Spectroscopic and thermogravimetric analyses demonstrate only a limited degradation of PEG-fluorescein upon irradiation of the particles up to 10 h using a thermal neutron flux of 5 × 10(16) m(-2) s(-1). Cell experiments show that the polyarginine-based mechanisms of membrane penetration remain unaltered after exposure of the functionalized particles to the mixed field of neutrons and gammas present during activation. This confirms that radiation damage on the PEG-polyarginines is minimal. Intrinsic radiations from (166)Ho do not seem to affect the integrity of conjugated organic material. These findings open up a new perspective to simplify the procedures for the preparation of functionalized metal-based nanosystems that need to be activated by neutron irradiation in order to be applied for diagnostic and/or therapeutic purposes.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Fate of Organic Functionalities Conjugated to Theranostic Nanoparticles upon Their Activation

et al. 2015

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“…The simple reaction conditions, ease of product purification, the ability to use environmentally friendly solvents or run the process without solvents, economic viability, and excellent yields make this methodology attractive. The literature describes methods for carrying out the solvent-free Cu-catalyzed azide−alkyne cycloaddition reaction (CuAAC) to obtain some organic compounds using various catalytic systems such as copper nanoparticles (CuNP) or their clusters, 35 N-heterocyclic carbenes (NHCs), 36 complex catalyst [CuBr(PPh 3 ) 3 ] 37 or Cu(PPh 3 ) 2 NO 3 , 38 copper powder. 39 Only in one study by Thorwirth et al was solvent-free CuAAC carried out, including on polymers.…”

Section: ■ Introductionmentioning

confidence: 99%

Environment Friendly Process toward Functional Polyorganosiloxanes with Different Chemical Structures through CuAAC Reaction

Bezlepkina

Ardabevskaia

Klokova

et al. 2022

ACS Appl. Polym. Mater.

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Despite the presence of many methods, which were created to date for the preparation, functionalization, and vulcanization of polysiloxanes, the development of materials based on silicones remains relevant and requires the introduction of new approaches that combine such modern strategies as atom-economical reactions, refusal to use harmful and dangerous organochlorosilanes, and using the principles of green chemistry and minimizing the use of solvents. In this work, we develop modern approaches to the preparation of both linear and branched polyorganosiloxanes containing azidopropyl functions at the silicon atom. In the first part of the work, it was shown that the proposed method for introducing these groups by catalytic rearrangement with the opening of cyclosiloxane is effective and makes it possible to obtain polysiloxanes with different contents of azidopropyl groups and different molecular weights. The second part of the work demonstrated the possibility of postpolymerization functionalization of such polymers by the mechanism of azide–alkyne cycloaddition under “green” conditions, without using solvents and amines. All of the most important functional fragments were introduced into the structures of organosilicon polymers by a single mechanism, under simple conditions, without the use of expensive catalysts, exposure to irradiation, and hazardous solvents. The combination of simplicity and versatility in the preparation of polysiloxanes with azidopropyl groups with the possibility of performing a click reaction makes it possible to directionally obtain the required materials based on universal raw materials and, as a result, can open up broad prospects for serious development and rethinking of the chemistry of silicones.

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“…Unsurprisingly, the deposition of clickable groups (azide or acetylenes) on a substrate gained much attention, given the unique characteristics of a "click" type reaction: high selectivity, low byproduct formation, and mild reaction condition. 14 This enables quantitative conversion and high yield of building blocks onto a surface. Servinis et al employed an electrochemical deposition method to tether a small molecule with an alkynyl end group to a CF surface and added azides afterward.…”

Section: Introductionmentioning

confidence: 99%

Latent, Cross-Linkable Triazole Platform on a Carbon Fiber Surface for Enhancing Interfacial Cross-Linking within Carbon Fiber/Epoxy Composites

2022

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A long-running need in carbon fiber composite production is to ameliorate interfacial adhesion between the polymer and carbon fibers. Here, we present a convenient and feasible strategy for controlling the carbon fiber’s surface in a continuous process: syntheses of click-modified silanes via copper(I)-catalyzed azide–alkyne cycloaddition reaction and grafting them onto fiber surfaces which prepare a latent curable platform under mild processes without postmodification. As 1,2,3-triazole moieties from the click reaction were added to the epoxy/dicyandiamide system, they triggered additional reactions in the later conversion stage; approximately, a 20% increase in the total reaction enthalpy compared to the system with no additives was obtained. We expected the enhanced cross-linking between the surface and matrix to expand the interfacial area, leading to reinforcements on interfacial adhesion and stress-transfer abilities within composites. The merit of the approach is well-demonstrated by conductive atomic force microscopy, showing that the interphase can be extended up to 6-fold when the triazole platform acts as curatives and serve as bridges after the epoxy cure. Consequently, the composite’s interfacial shear strength and interlaminar shear strength were increased up to 78 and 72%, respectively. This work affords a reactive platform where a custom-tailored fiber/matrix interface can be designed by virtue of versatility in clickable reactants.

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ChemInform Abstract: [CuBr(PPh₃)₃] for Azide—Alkyne Cycloaddition Reactions under Strict Click Conditions.

Cited by 5 publications

References 1 publication

Fate of Organic Functionalities Conjugated to Theranostic Nanoparticles upon Their Activation

Fate of Organic Functionalities Conjugated to Theranostic Nanoparticles upon Their Activation

Environment Friendly Process toward Functional Polyorganosiloxanes with Different Chemical Structures through CuAAC Reaction

Latent, Cross-Linkable Triazole Platform on a Carbon Fiber Surface for Enhancing Interfacial Cross-Linking within Carbon Fiber/Epoxy Composites

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ChemInform Abstract: [CuBr(PPh3)3] for Azide—Alkyne Cycloaddition Reactions under Strict Click Conditions.

Cited by 5 publications

References 1 publication

Fate of Organic Functionalities Conjugated to Theranostic Nanoparticles upon Their Activation

Fate of Organic Functionalities Conjugated to Theranostic Nanoparticles upon Their Activation

Environment Friendly Process toward Functional Polyorganosiloxanes with Different Chemical Structures through CuAAC Reaction

Latent, Cross-Linkable Triazole Platform on a Carbon Fiber Surface for Enhancing Interfacial Cross-Linking within Carbon Fiber/Epoxy Composites

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Product

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ChemInform Abstract: [CuBr(PPh₃)₃] for Azide—Alkyne Cycloaddition Reactions under Strict Click Conditions.