Fluorescent imidazole-based chemosensors for the reversible detection of cyanide and mercury ions†,Photochemical & Photobiological Sciences

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Fluorescent imidazole-based chemosensors for the reversible detection of cyanide and mercury ions†
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2018-09-22 00:00:00 , DOI: 10.1039/c8pp00226f
Ganapathi Emandi _{1,

2,

3,

4,

5} , Keith J. Flanagan _{1,

2,

3,

4,

5} , Mathias O. Senge _{1,

2,

3,

4,

5}

Affiliation

We report 4-(2-(5-(tert-butyl)-3-formyl-2-hydroxyphenyl)-1H-phenanthro[9,10-d]imidazol-1-yl)benzoic acid 1 and 4-(2-(5-(tert-butyl)-3-formyl-2-hydroxyphenyl)-4,5-diphenyl-1H-imidazol-1-yl)benzoic acid 2 as reversible luminescent sensors for the detection of cyanide and mercury ions. These imidazole derivatives were characterized using spectroscopic techniques and single crystal X-ray crystallography. The compounds showed sensing exclusively towards CN⁻ ions, which resulted in the quenching of fluorescence and a decreased singlet state life time. The detection limit of imidazole derivatives 1 and 2 were found to be 0.8 μM and 1.2 μM respectively, in a CH₃CN/H₂O system. Job's plot analysis, ¹H NMR spectra and LC-MS studies supported the formation of the respective cyanohydrin. This cyanohydrin was further used as a reversible sensor for the detection of Hg²⁺ ions through metal-assisted elimination. The reversibility and reusability of sensors for the detection of CN⁻ and Hg²⁺ ions were tested for four consecutive cycles.

中文翻译：

基于荧光咪唑的化学传感器，用于可逆检测氰化物和汞离子†

我们报告4-（2-（5-（叔丁基）-3-甲酰基-2-羟苯基）-1 H-菲[9,10 - d ]咪唑-1-基）苯甲酸1和4-（2 -（5-（叔丁基）-3-甲酰基-2-羟基苯基）-4,5-二苯基-1 H-咪唑-1-基）苯甲酸2作为可逆发光传感器，用于检测氰化物和汞离子。使用光谱技术和单晶X射线晶体学对这些咪唑衍生物进行表征。化合物表现出只朝向CN传感^-离子，这导致荧光的猝灭和降低的单重态寿命。咪唑衍生物1和在CH ₃ CN / H ₂ O系统中，发现2个分别为0.8μM和1.2μM 。Job's图分析，¹ H NMR光谱和LC-MS研究支持了各自氰醇的形成。该氰醇还进一步用作可逆传感器，用于通过金属辅助消除来检测Hg ²⁺离子。可逆性和用于检测CN的传感器的可重用性^-和Hg ²⁺离子连续四个周期进行了测试。

更新日期：2018-09-22

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