Nanomagnetic macrocyclic Schiff-base-Mn(ii) complex: an efficient heterogeneous catalyst for click approach synthesis of novel β-substitued-1,2,3-triazoles.

Abstract

In the present work, a novel symmetrical 15-membered macrocyclic Schiff base complex of manganese was prepared using the reaction of the synthetic 2,6-diacetylpyridine functionalized Fe3O4 MNPs with 2,2-(piperazine-1,4-diyl)dianiline and Mn(ii) bromide salt via a template approach. The resulting [Fe3O4@PAM–Schiff-base–Mn][ClO4] heterogenized complex was characterized using FT-IR, XRD, BET, TGA, EDX, Xray-mapping, SEM, TEM and VSM analysis. To demonstrate proof of concept, Huisgen 1,3-dipolar cycloaddition synthesis of 1,2,3-triazoles was selected to evaluate the activity and reusability of the catalyst. The ethanol as a green solvent proved to be an excellent reaction medium for this synthesis. Yields of up to 100% were obtained in some cases. Significantly, as demonstrated, [Fe3O4@PAM–Schiff-base–Mn][ClO4] catalyst was recycled for 8 cycles without losing catalytic activity under the optimized reaction conditions. The hot filtration and ICP-OES tests ratified that there was no leaching of metal during the catalytic reaction, indicating the heterogeneous manner of the catalyst.