荧光探针8-萘重氮氨基-2-硫代苯并噻唑的合成及性质研究

STUDY ON SYNTHESIS AND PERFORMANCE OF FLUORESCENT PROBE 8-NAPHTHALENEDIAZOAMINO-2-THIOBENZOTHIAZOLE

以1-萘胺为原料,在酸性溶液中与亚硝酸钠发生重氮化反应生成重氮盐,进一步和2-巯基苯并噻唑偶联合成一种新型的荧光试剂8-萘重氮氨基-2-硫代苯并噻唑(NADTBT)。合成产率为40.7%,提纯后产物表观为红褐色粉末的固体,具有乙醇溶解性。通过红外光谱、荧光光谱和高效液相色谱及质谱进行表征。实验结果表明,引入了噻唑环结构,增加了NADTBT分子刚性的平面结构,使其具有明显不同于萘胺的荧光性能,最佳激发/发射波长为225 nm/366 nm,荧光量子产率为5.82%。NADTBT分子中的偶氮结构可与金属离子形成配位化合物,导致荧光强度发生变化。其中,铜离子的猝灭响应最为明显,可为铜离子的检测提供一种新型的荧光检测探针。荧光猝灭程度与铜离子的浓度在(1.00~9.00)×10-6 mol/L浓度范围内,呈良好的线性关系,相关系数r=0.9955。

A novel fluorescent reagent 8-naphthalenediazoamino-2-thiobenzothiazole(NADTBT)was synthesized by diazotization coupling reaction with 1-naphthylamine and sodium nitrite in an acidic solution to form a diazonium salt,it reacts with which is further coupled with 2-mercaptobenzothiazole.The synthesis yield was 40.7%.After purification,the product appeared as a red-brown powder solid with alcohol solubility.The structure of NADTBT was characterized by infrared spectroscopy,fluorescence spectroscopy,high performance liquid chromatography and mass spectrometry.The experimental results showed that the introduction of the thiazole structure increases the planar structure of the NADTBT molecular rigidity,which makes it had a fluorescence performance that is significantly different from 1-naphthylamine.The excitation/emission wavelength was 225 nm/366 nm and the fluorescence quantum yield is 5.82%.The azo structure in NADTBT molecules could form coordination compounds with metal ions,resulting in changes in fluorescence intensity.The most obvious quenching response was shown by copper ions with NADTBT,which could provide a new type of fluorescent detection probe for the detection of copper ions.The degree of fluorescence quenching and the concentration of copper ions shows a good linear relationship in a certain range of(1.009.00)×10-6 mol/L,and the correlation coefficient r=0.9955.