水杨醛席夫碱Zn^(2+)荧光探针的合成及性能研究  

Fluorescent probes for Zn^(2+)ions synthesized based on salicylaldehyde Schiff-bases

作　　者：李中燕 李元达 杨芊之 张胜婷 袁霖 LI Zhong-yan;LI Yuan-da;YANG Qian-zhi;ZHANG Sheng-ting;YUAN Lin(School of Chemical and Biological Engineering,Hunan University of Science and Engineering,Yongzhou 425199,China)

机构地区：[1]湖南科技学院化学与生物工程学院,湖南永州425199

出　　处：《化学研究与应用》2022年第10期2552-2557,共6页Chemical Research and Application

基　　金：湖南省教育厅科学研究项目(21A0518)资助;湖南省教育厅科学研究项目(21C0691)资助。

摘　　要：设计合成了三种新型的席夫碱Zn^(2+) 荧光探针,5-氯水杨醛缩叔丁胺( L1 )、5-溴水杨醛缩叔丁胺( L2 )和5-硝基水杨醛缩叔丁胺( L3 ),结构均由^(1)H NMR、^(13)C NMR、IR和HRMS进行了表征。荧光光谱分析实验结果表明,相比于探针 L2和L3 ,探针 L1 对Zn^(2+) 具有更好的选择性和灵敏度,检出限为66 nmol·L^(-1) ,远低于国标GB5749-2006《生活饮用水卫生标准》规定的饮水中Zn^(2+) 含量的限量值。在0~10 μmol·L^(-1) 浓度的范围内,探针 L1 的荧光强度与Zn^(2+) 浓度可呈现良好的线性关系。同时,Job曲线证实探针 L1 与Zn^(2+) 以摩尔比2∶1络合,并通过核磁滴定、红外光谱实验和单晶结构进一步确定了 L1 与Zn^(2+) 络合机理。在活体生物Zn^(2+) 检测中,探针 L1 具有良好的生物相容性,表明其在水体及水体生物Zn^(2+) 检测中具有潜在的应用前景。Three novel Schiff-base fluorescent probes,2-((tert-butylimino)methyl)-4-chlorophenol( L1 ),4-bromo-2-((tert-butylimino)methyl)phenol( L2 ),2-((tert-butylimino)methyl)-4-nitrophenol( L3 ),were synthesized and characterized by^(1)H NMR,^(13)C NMR,IR and HRMS.The results of fluorescence spectrum analysis showed that the probe L1 ,was more selective and sensitive to Zn^(2+) than probes L2 and L3 . The detection limit of L1 was found to be 66 nmol·L^(-1) ,which was far lower than the limit value of Zn^(2+) content in drinking water,stipulated in the national standard GB5749-2006“Sanitary Standards for Drinking Water”. There was a good linear relationship between the fluorescence intensity of the probe L1 and the concentration of Zn^(2+) in the range of 0 to 10 μmol·L^(-1) . Mean the while,the Job plot revealed a 2∶1 L1 -Zn^(2+) identification.The complexation mechanism of L1 with Zn^(2+) was further determined by^(1)H NMR titration,infrared spectroscopy and single crystal.In the detection of Zn^(2+) in living organisms,the probe L1 had good biocompatibility,indicating that it had a potential application prospect in the detection of Zn^(2+) in water and aquatic organisms.

关 键 词：水杨醛 席夫碱 锌离子 荧光探针 活体检测 

分 类 号：O624.41[理学—有机化学]