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负载于磁铁矿-壳聚糖上的磺化席夫碱作为合成呫吨衍生物的高效纳米催化剂

Sulfonated Schiff base immobilized on magnetite-chitosan as an efficient nanocatalyst for the synthesis of xanthene derivatives.

作者信息

Taheri Mohammadhossein Alijafari, Setoodehkhah Moslem, Moradian Mohsen

机构信息

Department of Inorganic chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran.

Department of Organic chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran.

出版信息

Sci Rep. 2025 May 30;15(1):19056. doi: 10.1038/s41598-025-03308-w.

DOI:10.1038/s41598-025-03308-w
PMID:40447651
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12125304/
Abstract

The present study aims to develop and enhance a magnetic heterogeneous catalyst with a core-shell structure, FeO@CS/SSB (FeO@Chitosan-Salicylaldehyde-5-sulfonate), by immobilizing a chitosan-based Schiff base complex on the surface of magnetite. Chitosan, a low-cost, biodegradable, and biocompatible polymer with a suitable chemical structure such as the NH₂ functional group plays a significant role in heterogeneous catalytic systems. In this research, the Schiff base was synthesized through the condensation of a sulfonated aromatic aldehyde (salicylaldehyde) with the amine group of chitosan, forming a magnetic nanocatalyst with acidic properties. The catalyst was characterized using various analytical techniques, including XRD, FT-IR, VSM, TGA, DLS, FE-SEM, EDX, and TEM. The catalytic performance of the nanomagnetic catalyst was evaluated in the synthesis of 14-aryl-14-H-dibenzo[a, j]xanthenes and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones via a one-step condensation reaction of dimedone, 2-naphthol, and aryl aldehydes in ethanol. The progress of the reaction was monitored using thin-layer chromatography (TLC). The xanthenes derivatives were characterized by FT-IR, H NMR, and C NMR analyses. Ultimately, it was observed that the catalyst could be reused multiple times without significant loss of catalytic activity.

摘要

本研究旨在通过将基于壳聚糖的席夫碱配合物固定在磁铁矿表面,开发并增强一种具有核壳结构的磁性非均相催化剂FeO@CS/SSB(FeO@壳聚糖-水杨醛-5-磺酸盐)。壳聚糖是一种低成本、可生物降解且具有生物相容性的聚合物,具有合适的化学结构,如NH₂官能团,在非均相催化体系中发挥着重要作用。在本研究中,席夫碱是通过磺化芳香醛(水杨醛)与壳聚糖的胺基缩合而成,形成了一种具有酸性的磁性纳米催化剂。使用各种分析技术对催化剂进行了表征,包括XRD、FT-IR、VSM、TGA、DLS、FE-SEM、EDX和TEM。通过在乙醇中使达米酮、2-萘酚和芳醛一步缩合反应,评估了纳米磁性催化剂在合成14-芳基-14-H-二苯并[a,j]呫吨和12-芳基-9,9-二甲基-8,9,10,12-四氢苯并[a]呫吨-11-酮中的催化性能。使用薄层色谱(TLC)监测反应进程。通过FT-IR、¹H NMR和¹³C NMR分析对呫吨衍生物进行了表征。最终观察到,该催化剂可以多次重复使用而不会显著损失催化活性。

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