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首页> 外文期刊>RSC Advances >One-pot synthesis of functionalized 4-hydroxy-3-thiomethylcoumarins: detection and discrimination of Co2+ and Ni2+ ions
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One-pot synthesis of functionalized 4-hydroxy-3-thiomethylcoumarins: detection and discrimination of Co2+ and Ni2+ ions

机译：一锅合成功能化的4-羟基-3-硫代甲基香豆素：检测和区分Co2 +和Ni2 +离子

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摘要

A wide variety of 4-hydroxy-3-thiomethylcoumarin derivatives were synthesized through a one-pot three-component reaction from 4-hydroxycoumarin, aldehydes and thiols, catalysed by L-proline in ethanol at room temperature, in moderate to good yields. The present protocol offers many advantages such as milder reaction conditions, green solvent, easy work up procedure and requirement of a smaller amount of catalyst. Furthermore, one of the derivatives (30a) has been successfully employed as a "turn-off" fluorescence probe that displays remarkable changes in its optical properties only in the presence of cobalt and nickel ions in aqueous based media. The ligand (30a) showed high selectivity towards Co2+ & Ni2+ without any interference from other commonly coexisting metal ions. Fluorescence quenching of ligand (30a) by Co2+ & Ni2+ was found to be similar to 80% and similar to 85% respectively in 9 : 1 DMSO/HEPES buffer (pH = 7.4, 10 mM) at room temperature. Significant changes in the UV-vis spectra with a clear formation of isosbestic points confirms the formation of ligand-metal complexes. The predicted binding mode (2 : 1) for ligand-metal was observed from High Resolution Mass Spectroscopy, Job's plots and single crystal X-ray structures of the complexes. The lower stability of the cobalt(II) complex than the nickel(II) complex provides a reliable platform to distinguish Co2+ from Ni2+ via a "turn-on" photoluminescence response towards the disodium salt of ethylenediaminetetraacetic acid (EDTA).
机译：在室温下，乙醇中L-脯氨酸催化4-羟基香豆素，醛和硫醇通过一锅三组分反应合成了多种4-羟基-3-硫代甲基香豆素衍生物。本方案具有许多优点，例如反应条件温和，绿色溶剂，后处理容易并且需要较少量的催化剂。此外，一种衍生物（30a）已成功地用作“截止”荧光探针，其仅在水基介质中存在钴和镍离子时才显示出其光学性能的显着变化。配体（30a）对Co2 +和Ni2 +具有很高的选择性，而不受其他常见共存金属离子的干扰。发现在室温下，在9：1 DMSO / HEPES缓冲液（pH = 7.4，10 mM）中，Co2 +和Ni2 +对配体（30a）的荧光猝灭分别类似于80％和85％。 UV-vis光谱的明显变化以及等渗点的清晰形成证实了配体-金属配合物的形成。从高分辨率质谱，Job's图和配合物的单晶X射线结构观察到配体-金属的预测结合模式（2：1）。钴（II）配合物比镍（II）配合物的稳定性低，提供了可靠的平台，可通过对乙二胺四乙酸二钠盐（EDTA）的“开启”光致发光反应来区分Co2 +与Ni2 +。

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