An expedient ‘click’ approach for the synthetic evaluation of ester‐triazole‐tethered organosilica conjugates

Abstract

The present work articulates the synthesis of a new series of organo‐functionalized triethoxysilanes derived from versatile carboxylic acids and 3‐azidopropyltriethoxysilane in excellent yields. A proficient and convenient route implicating the Cu(I)‐catalysed 1,3‐cycloaddition of organic azide with terminal alkynes, labelled as click silylation, has been developed for the generation of ester‐triazole‐linked alkoxysilanyl scaffolds (4a–f). All the synthesized compounds have been thoroughly characterized using elemental analysis and Fourier transform infrared, 1H NMR and 13C NMR spectroscopic techniques. Importantly, the fabricated alkoxysilanes are potentially amenable for an in situ sol–gel condensation reaction with silica nanospheres leading to the incorporation of organic functionality via covalent grafting onto the nanostructured particle system. As a proof of concept, a one‐pot preparation of organic–inorganic hybrid nanoparticles is presented using bis‐silane 4 f. The efficiency and selectivity of the prepared nanocomposite towards metal ions is highlighted using adsorption experiments, and the immobilized nanoparticles present a high sensing efficiency towards Cu2+ and Pb2+ ions while demonstrating better response than that of the bulk material.

Intriguing interactions of triazolyl organosilane with copper (II) ion, blue copper protein, and silica nanoparticles: Spectral and theoretical approach

“…The coppercatalyzed azide-alkyne cycloaddition (CuAAC) reaction is the most promising method and furnishes leisure for numerous reactions with high level of precision and control. [31,32] 1,2,3-triazole scaffold has substantiated to be a competent binding skeleton, and their prevalence in chemosensors can be accredited to their ability to bind cations by providing nitrogen donor sites. [33,34] Moreover, organosilanes have multifaceted applicability in optical sensing, drug delivery, and polymer chemistry and are promising materials to increase the adhesion of organic matrices to inorganic substrates.…”