一种苝酰亚胺Pb^(2+)荧光探针的合成及其选择性识别

Synthesis and Selective Identification of a Pb^(2+) Fluorescent Probe Based on Perylenediimide

以四氯苝酐、3-氨甲基吡啶为原料,设计并合成了一种可选择性识别Pb^(2+)的新型苝酰亚胺类荧光探针N,N-(吡啶-3-甲基)-1,6,7,12-四氯-3,4:9,10-苝二酰亚胺(PDI-MBD)。采用质谱、核磁等检测手段对其分子结构进行了表征,通过紫外和荧光光谱法对目标化合物PDI-MBD在N-甲基-2-吡啶烷酮(NMP)/H2O溶液中,对Pb^(2+)的识别性能进行了研究,其光谱性能和对Pb^(2+)识别研究显示,探针PDI-MBD自身的荧光较弱,但与金属离子Pb^(2+)配位反应后荧光显著增强,为配位反应前的10倍,但随着时间的延长,之后又出现荧光猝灭的现象。探针PDI-MBD表现出对溶液中的Pb^(2+)具有良好的选择性识别,且灵敏度高。研究发现,Pb^(2+)在0.1×10^(-5)~5×10^(-5)mol/L的浓度范围内与探针的荧光强度存在良好的线性关系;Pb^(2+)的最低检测限为0.5×10^(-6)mol/L。抗干扰试验证明加入其他常见金属离子后,探针PDI-MBD对Pb^(2+)的荧光信号无显著变化,不易受其他金属离子的影响。说明PDI-MBD可作为Pb^(2+)荧光探针,具有较优的选择性和较强的灵敏度,建立了一种检测Pb^(2+)的分析方法。

A new fluorescent probe of perylenediimide derivative,N,N-(pyridine-3-methyl)-1,6,7,12-tetrachloro-3,4:9,10-perylene diimide(PDI-MBD),was designed and synthesized from tetrachloroperylene tetrahydride and 3-aminomethyl pyridine.The molecular structure of PDI-MBD was characterized by MS and ^(1)H NMR.The Pb^(2+)recognition performance of PDI-MBD in N-methyl-2-pyrrolidinone(NMP)/H 2O was studied in detail by UV and fluorescence spectroscopy.Its spectral properties and the studies on Pb^(2+)recognition showed that the fluorescence of PDI-MBD was weak,but the fluorescence significantly enhanced after the coordination reaction with Pb^(2+),which was ten times before the coordination reaction.However,with the extension of time,the phenomenon of fluorescence quenching appeared again.PDI-MBD probe showed good selective recognition and high sensitivity to Pb^(2+)in solution.It was found that Pb^(2+)had a good linear relationship with the fluorescence intensity of probe in the concentration range of 0.1×10^(-5)~5×10^(-5)mol/L.The lowest detection limit to Pb^(2+)was 0.5×10^(-6)mol/L.The anti-interference experiment showed that the fluorescence signal of Pb^(2+)did not significantly change after adding other common metal ions,and it is not easy to be interfered by other metal ions.These results indicated that PDI-MBD can be used as a Pb^(2+)fluorescent probe with better selectivity and sensitivity,and a analytical method for detecting Pb^(2+)has been established.