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二茂铁基三唑配合物及其在重金属阳离子传感中的应用。

Ferrocenyl-triazole complexes and their use in heavy metal cation sensing.

作者信息

Al Khalyfeh Khaled, Ghazzy Asma, Al-As' Ad Randa M, Rüffer Tobias, Kanoun Olfa, Lang Heinrich

机构信息

Department of Chemistry, Faculty of Natural Science, Al-Hussein Bin Talal University Ma'an 71111 Jordan

Faculty of Pharmacy, Faculty of Pharmacy and Applied Medical Sciences, Al-Ahliyya Amman University Amman 19328 Jordan.

出版信息

RSC Adv. 2024 Jun 28;14(29):20572-20584. doi: 10.1039/d4ra04023f. eCollection 2024 Jun 27.

Abstract

Complexes tris((1-ferrocenyl-1-1,2,3-triazol-4-yl)methyl)amine (3), bis((1-ferrocenyl-1-1,2,3-triazol-4-yl)methyl)amine (6), bis((1-ferrocenyl-1-1,2,3-triazol-4-yl)methyl)ether (7), and 1-ferrocenyl-1-1,2,3-triazol-4-yl)methanamine (9) were synthesized using the copper-catalyzed click reaction. Complexes 3, 6, 7, and 9 were characterized using NMR (H and {H}) and IR spectroscopy, elemental analysis, and mass spectrometry. Structures of 3, 7, and 9 in the solid state were determined using single-crystal X-ray diffraction. It was found that the triazole rings were planar and slightly twisted with respect to the cyclopentadienyl groups attached to them. Chains and 3D network structures were observed due to the presence of π⋯π and C-H⋯N interactions between the cyclopentadienyl and triazole ligands. A reversible redox behavior of the Fc groups between 239 and 257 mV with multicycle stability was characteristic for all the compounds, revealing that the electrochemically generated species Fc remained soluble in dichloromethane. Electrochemical sensor tests demonstrated the applicability of all the complexes to enhance the quantification sensing behavior of the screen-printed carbon electrode (SPCE) toward Cd, Pb, and Cu ions.

摘要

通过铜催化的点击反应合成了三((1-二茂铁基-1-1,2,3-三唑-4-基)甲基)胺配合物(3)、双((1-二茂铁基-1-1,2,3-三唑-4-基)甲基)胺(6)、双((1-二茂铁基-1-1,2,3-三唑-4-基)甲基)醚(7)和1-二茂铁基-1-1,2,3-三唑-4-基)甲胺(9)。使用核磁共振(H和{H})、红外光谱、元素分析和质谱对配合物3、6、7和9进行了表征。通过单晶X射线衍射确定了固态下3、7和9的结构。发现三唑环是平面的,相对于连接在其上的环戊二烯基略有扭曲。由于环戊二烯基和三唑配体之间存在π⋯π和C-H⋯N相互作用,观察到了链状和三维网络结构。所有化合物的Fc基团在239至257 mV之间具有可逆的氧化还原行为且具有多循环稳定性,这表明电化学生成的物种Fc在二氯甲烷中保持可溶。电化学传感器测试证明了所有配合物在增强丝网印刷碳电极(SPCE)对Cd、Pb和Cu离子的定量传感行为方面的适用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/60cd/11211737/959df5adc9c6/d4ra04023f-s1.jpg

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