Fluorescent probe based on N-ethyl carbazol-3-formaldehyde Schiff-base: Synthesis and properties of Cu2+ detection
董智云 忻州师范学院化学系, 忻州 034000  
郭昌晟 忻州师范学院化学系, 忻州 034000  
高琳 忻州师范学院化学系, 忻州 034000  
顼兴宇 忻州师范学院化学系, 忻州 034000  
刘成琪 忻州师范学院化学系, 忻州 034000  
席福贵 忻州师范学院化学系, 忻州 034000 xifugui@163.com 
摘要: 以咔唑为原料,经过两步反应制备得到N-乙基咔唑-3-甲醛,其结构经X射线单晶衍射测定属于单斜晶系,空间群为P21/n。再以N-乙基咔唑-3-甲醛与1,3-二氨-2-丙醇为原料,设计、合成了一种新型双席夫碱荧光探针分子CMP。借助荧光光谱在体积比为6:4的DMSO/H2O缓冲溶液(Tris-HCl,pH=7.0)中研究了探针CMP对Cu2+的选择性识别。研究结果表明,探针CMP与Cu2+以1:2的比例配位,结合常数为1.52×105 L·mol-1,检出限为0.205 μmol·L-1。回收实验表明,探针分子CMP可应用于环境水样中Cu2+的检测。
关键词: N-乙基咔唑-3-甲醛  席夫碱  荧光探针  Cu2+  荧光猝灭
基金项目: 国家自然科学基金(No.21701137)和山西省高等学校科技创新项目(No.2021L449,2021L455)资助。
Abstract: N-ethyl carbazol-3-formaldehyde was synthesized by using carbazole as initial material through a two-step reaction, and its crystal structure was determined by X-ray single crystal diffraction and showed that the crystal belongs to monoclinic, P21/n space group. A new fluorescent probe CMP for Cu2+ ions was designed and synthesized from N-ethyl carbazol-3-formaldehyde and 1,3-diamino-2-propanol. CMP in DMSO/H2O (6:4, V/V, Tris-HCl buffer, pH=7.0) solution displayed highly selective and sensitive fluorescence "on-off" response over all the other competitive metal ions including K+, Ni2+, Pb2+, Sn2+, Mn2+, Fe3+, Fe2+, Cr3+, Co2+, Cd2+, Al3+, and Mg2+. The fluorescence intensity of CMP presented a good linear relationship to the Cu2+ concentration and with a low detection limit of 0.205 μmol·L-1 for Cu2+ ion, and the binding constant was calculated to be 1.52×105 L·mol-1. 1/(I0-I) of CMP vs cCu2+/cCMP plot, Job plot, and 1H NMR titration confirmed that fluorescence decrease was caused by the formation of 1:2 complex between CMP and copper ion. The recovery tests demonstrated that CMP could accurately detect the existence of Cu2+ ions in water samples. CCDC:2156980, N-ethyl carbazol-3-formaldehyde.
Keywords: N-ethyl carbazol-3-formaldehyde  Schiff base  fluorescent probe  Cu2+  fluorescence quenching
投稿时间:2022-11-21 修订日期:2023-01-18
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