水杨醛肼二腙类聚集诱导发光染料合成及对F^(-)的检测

Synthesis of AIEgen Based on Salicylaldehyde Azine and Its Application in Detection of F^(-)

研究开发了1个具有ESIPT+AIE性能的分子5-甲基水杨醛肼二腙(5-Me-SAA),并用于识别检测F^(-)。基于ESIPT性能,5-Me-SAA的稀溶液呈现烯醇式(E)和酮式(K)的双发射,K式发射峰随溶剂极性的增大而下降。5-Me-SAA在四氢呋喃稀溶液中处于自由分散状态,荧光发射较弱;在纯水中形成聚集体,荧光增强22倍,表现出AIE性能。此外,5-Me-SAA可通过裸眼和荧光双通道快速选择性识别F^(-),且响应灵敏,检测限为0.64μmol·L^(-1)。进一步利用核磁共振氢谱探究了探针与F^(-)的作用机理,结果表明在F^(-)作用下,探针的酚羟基发生去质子化,光学性质随之改变。

In this paper,a typical AIEgen 5-methylsalicylaldehyde azine(5-Me-SAA)with ESIPT behavior is developed,synthesized and applied in the detection of F^(-).The dilute solution of 5-Me-SAA has presented double emission of enol(E)and keto(K)forms as a result of ESIPT performance,and the ratio of K/E declines when the polarity of solvent increases.5-Me-SAA is freely dispersed in THF and the fluorescence is weak whereas aggregates are formed in pure water and the emission is enhanced by 22 times,showing a significant AIE effect.In addition,5-Me-SAA can quickly and selectively detect F^(-)with naked eye and fluorescence enhancement.Moreover,it exhibits good sensitivity and the limit of detection(LOD)is calculated as low as 0.64μmol·L^(-1).The interaction mechanism between 5-Me-SAA and F^(-)is further explored by H^(1)-NMR.The result demonstrates that F^(-)triggers the deprotonation of —OH and affects the optical properties of probe.