Computational and Experimental Investigation of Immobilization of CuI Nanoparticles on 3-Aminopyridine Modified Poly(styrene-co-maleic anhydride) and Its Catalytic Application in Regioselective Synthesis of 1,2,3-Triazoles

Abstract

Cu(I) nanoparticles (NPs) on modified poly(styrene-co-maleic anhydride) was prepared via a facile procedure. In this regard the modified co-polymer (SMA) was initially synthesized from the reaction of poly(styrene-co-maleic anhydride) with 3-aminopyridine. Upon the treatment of CuI with SMA, Cu(I) NPs were immobilized on SMA. This immobilized Cu(I) NPs was fully characterized by FTIR, SEM and EDAX analysis methods. Moreover, the interaction of Cu cations with 3-aminopyridine modified SMI catalyst via density functional theory (DFT) and quantum theory of atoms in molecules (QTAIM) computationally was studied. Our calculated results demonstrated that among 2,3 and 4 substituted aminopyridines for the modification of SMA, the 3-amnopyridine has the weakest ligand and Cu(I) interaction. However, the SMI image showed a suitable size of nanoparticles and inductively coupled plasma (ICP) analysis showed a higher Cu content in comparison with those of 2 and 4-substituted pyridines. The catalytic activity and reusability of this nanocatalyst system of 3-substituded aminopyridines was examined in the Huisgen 1,3-dipolar cycloaddition via click reaction. The reactions proceeded smoothly leading to regioselective synthesis of 1,4-disubstitued 1,2,4-triazole derivatives in excellent yields under mild reaction conditions. This heterogeneous catalytic system was separated easily by simple filtration and was reused without pre-activation at least in five runs without appreciable loss in its activity.

Ultrasonic and bio‐assisted synthesis of Ag@HNTs‐T as a novel heterogeneous catalyst for the green synthesis of propargylamines: A combination of experimental and computational study

“…As it was discussed earlier, we have recently focused on the joint experimental and computational assessment of heterogeneous catalysts including modified poly (styrene‐co‐maleic anhydride) palladium and copper nanocatalyst, copper (I) and (II) ‐aminated KIT‐5 and N‐sulfamic‐aminated KIT‐5 catalysts . Armed with these experiences, we present a quantitative model for description of immobilization behavior of Ag NPs on functionalized HNTs support via DFT and PCM computational approaches.…”

“…Based on our focus on combined experimental and computational design of heterogeneous nanocatalysts and their applications in organic reactions, we have recently analysed and reported metal‐ligand interactions between metal nanoparticles and several amine functionalized polymeric and silica bonded mesoporous supports from the structural, electronic and thermochemical viewpoints . Regarding the importance of information about the physicochemical properties of support surfaces in their computational design and applications, in this research we investigated computationally the immobilization behaviour of silver nanoparticles on 1 H ‐1,2,3‐triazole‐5‐methanol functionalized HNTs surface.…”

Direction of theoretical and experimental investigation into the mechanism of n-HA/Si-PA-SC@Ag as a bio-based heterogeneous catalyst in the reduction reactions

“…In line with our investigations on the design, synthesis and computational modeling of heterogeneous catalysts and development of ecologically benign methods for chemical synthesis [34][35][36][37][38][39] regarding the reports of researchers in the field of joining theory and experiments [40][41][42] , we have recently focused on the application of naturalheterogeneous catalysts in several organic conversions 19,[43][44][45] . Hence, we are introducing efficient catalysts using n-HA decoration with organic functionalities and Ag-NPs doping by bio-assisted method.…”

“…In this line, we have investigated the immobilization behavior of palladium and copper NPs on the modified poly (styrene-co-maleic anhydride) surface. In addition, immobilization of Cu nanoparticles on the aminated and N-sulfamic-aminated KIT-5 nanocatalysts, poly(methyl methacrylate-co-maleimide) support and various functionalized halloysite nanoclays were modeled using quantum chemistry approaches 34,37,[46][47][48][49][50][51][52] . In the recent year, we have assessed metal-ligand interactions in an appropriate designed model of n-hydroxyapatite supported-silver catalyst, functionalized with 4-aminoacetanilide 39 .…”

Valorization of natural clay as an ecological catalyst in the regioselective synthesis of some heterocyclic compounds based on 1,2,3-triazoles

“…Kumar and co-workers reported the synthesis of triazoles using copper-catalyzed azidealkyne (CuAAC) and Ru-catalyzed azide-alkyne cycloaddition (RuAAC) [22]. Application in the regioselective synthesis of 1,2,3-triazoles using CuI nanoparticles on 3-aminopyridine modified poly(styrene-c-maleic anhydride) as catalyst was reported by Hossiennejad et al [23]. Khaled et al [24] applied the copper oxide chitosan nanocomposite for the green regioselective synthesis of 1,2,3-triazoles.…”