三种水杨醛席夫碱荧光探针的合成及对Zn^(2+)的识别

Three Salicylaldehyde Schiff Base Fluorescent Probes: Synthesis and Recognition of Zn^(2+)

设计、合成了3种新型席夫碱Zn^(2+)荧光探针:水杨醛缩三羟甲基氨基甲烷(L1)、5-氯水杨醛缩三羟甲基氨基甲烷(L2)和4-甲氧基水杨醛缩三羟甲基氨基甲烷(L3),并用^(1)H NMR、^(13)C NMR、元素分析和HRMS进行了表征。光谱分析实验结果表明,相比于探针L1和L3,探针L2对Zn^(2+)具有更好的选择性和灵敏度,检出限为11.96 nmol·L^(-1),远低于国标GB5749—2006规定的饮水中Zn^(2+)的限量值1.0 mg·L^(-1)(约15μmol·L^(-1))。在0-10μmol·L^(-1)范围内,探针L2的荧光强度与Zn^(2+)浓度可呈良好的线性关系。同时,配合物[Zn(C_(11)H_(13)ClNO_(4))_(2)](L2-Zn^(2+))的单晶结构和Job曲线证实探针L2与Zn^(2+)以物质的量之比2∶1配位。另外,探针L2能够对实际水样中的Zn^(2+)进行有效检测。

Three novel Schiff-base fluorescent probes, 2-((2-hydroxybenzylidene)amino)-2-(hydroxymethyl)propane-1,3-diol(L1), 2-((5-chloro-2-hydro-xybenzylidene)amino)-2-(hydroxymethyl)-propane-1,3-diol(L2), and 2-((2-hydroxy-4-methoxy-benzylidene)amino)-2-(hydroxymethyl)propane-1,3-diol(L3), were designed and synthesized,and characterized by ^(1)H NMR,^(13)C NMR, elemental analysis, and HRMS. The results of the spectral analysis showed that probe L2 was more selective and sensitive to Zn^(2+)than probes L1 and L3. The detection limit of L2 was found to be 11.96 nmol·L^(-1), which was far lower than the limit value of Zn^(2+)in drinking water, 1.0 mg·L^(-1)(about 15 μmol·L^(-1)), stipulated in the national standard GB5749—2006. There was a good linear relationship between the fluorescence intensity of probe L2 and the concentration of Zn^(2+)in a range of 0 to 10 μmol·L-1. Meanwhile, the singlecrystal structure of complex [Zn(C_(11)H_(13)ClNO_(4))_(2)](L2-Zn^(2+)) and the Job′s plot revealed a 2∶1 L2-Zn^(2+)identification.Moreover, probe L2 could detect Zn^(2+)in actual water samples. CCDC: 2121021, L2-Zn^(2+).