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Issue 3, 2020
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Highly modulated supported triazolium-based ionic liquids: direct control of the electronic environment on Cu nanoparticles

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Abstract

A series of new triazolium-based supported ionic liquids (SILPs), decorated with Cu NPs, were successfully prepared and applied to the N-arylation of aryl halides with anilines. The triazoles moieties were functionalised using copper-catalysed azide–alkyne cycloaddition. SILP surface characterisation showed a strong correlation between the triazolium cation volume and textural properties. STEM images showed well-dispersed Cu NPs on SILPs with a mean diameter varying from 3.6 to 4.6 nm depending on the triazolium cation used. Besides, XPS results suggest that the Cu(0)/Cu(I) ratio can be modulated by the electronic density of triazolium substituents. XPS and computational analysis gave mechanistic insights into the Cu NP stabilisation pathways, where the presence of electron-rich groups attached to a triazolium ring plays a critical role in leading to a cation adsorption pathway (Eads = 72 kcal mol−1). In contrast, less electron-rich groups favour the anion adsorption pathway (Eads = 63 kcal mol−1). The Cu@SILP composite with electron-rich groups showed the highest activity for the C–N Ullmann coupling reaction, which suggests that electron-rich groups might act as an electron-like reservoir to facilitate oxidative addition for N-arylation. This strategy firmly suggests the strong dependence of the nature of triazolium-based SILPs on the Cu NP surface active sites, which may provide a new environment to confine and stabilise MNPs for catalytic applications.

Graphical abstract: Highly modulated supported triazolium-based ionic liquids: direct control of the electronic environment on Cu nanoparticles

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Article information


Submitted
20 Jan 2020
Accepted
09 Feb 2020
First published
12 Feb 2020

This article is Open Access

Nanoscale Adv., 2020,2, 1325-1332
Article type
Paper

Highly modulated supported triazolium-based ionic liquids: direct control of the electronic environment on Cu nanoparticles

C. Valdebenito, J. Pinto, M. Nazarkovsky, G. Chacón, O. Martínez-Ferraté, K. Wrighton-Araneda, D. Cortés-Arriagada, M. B. Camarada, J. Alves Fernandes and G. Abarca, Nanoscale Adv., 2020, 2, 1325
DOI: 10.1039/D0NA00055H

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