Preparation And Properties Of Fluorescent Probes Based On 1,8-naphthalimide Derivatives

In recent years,with the continuous development of the fluorescent probes,the method of fluorescent probe detection has become one of the important ways of detecting the ions in the environment.It is an urgent problem to design and synthesize fluorescent probes with high sensitivity,simple synthesis and fast response.In this thesis,four fluorescent probes NADP,NADN,NAID and NAFH were designed and synthesized.The thesis also investigated the properties and applications of the probes.A novel fluorescent probe NADP for the determination of mercury was prepared by the reaction of 1,8-naphthalimide derivatives with 1,3-propanedithiol.The structure of the probe was analyzed and confirmed by ¹H NMR,¹³C NMR and HRMS.The UV absorption spectrum and fluorescence emission spectrum of the probe were measured in the presence of different ions.It was found that the fluorescent probe NADP had a specific response to mercury ions.The anti-interference ability,detection limit,applicable p H range,response time,cytotoxicity and biological application of the probe were also investigated.In addition,the reaction mechanism of fluorescent probe NADP for the detection of mercury ion was studied by ¹H NMR titration experiment and theoretical calculation.The final results implied that the fluorescent probe NADP has practical application value in detecting mercury ions in environment and biology.A novel fluorescent probe NADN for the determination of mercury was synthesized by the reaction of 1,8-naphthalimide derivatives with1,8-diaminonaphthalene.The structure of the probe was analyzed and confirmed by ¹H NMR,¹³C NMR and HRMS.The UV absorption spectrum and fluorescence emission spectrum of the probe were texted in the presence of various ions.It was found that fluorescent probe NADN had a specific response to mercury ions.The anti-interference ability,detection limit,applicable p H range,response time and visual application of the probe were also studied.In addition,the reaction mechanism of fluorescent probe NADN for the detection of mercury ions was explored by high-resolution mass spectrometry.Cells experiment exhibited that the probe NADN had been successfully applied to the imaging of mercury ions in living cells with excellent biocompatibility and low cytotoxicity.A novel fluorescent probe NAID for the determination of hypochlorous acid was prepared by the reaction of 1,8-naphthalimide derivatives with 1,3-indanedione.The structure of the probe was analyzed and confirmed by ¹H NMR,¹³C NMR and HRMS.The UV absorption spectrum and fluorescence emission spectrum of the probe were investigated in the presence of different ions.It was found that the fluorescent probe NAID had a specific response to hypochlorous acid with the significant change of fluorescence from"off"to"on".The anti-interference ability,detection limit,applicable p H range,response time,cytotoxicity and biological application of the probe were explored for the detection of hypochlorous acid.It was found that the probe had excellent detection performance for hypochlorous acid.In addition,the reaction mechanism of the probe NAID was studied by high distortion mass spectrometry.A novel fluorescent probe NAFH for the determination of hypochlorous acid was prepared by the reaction of 1,8-naphthalimide derivatives with 2-furoyl hydrazine.The structure of the probe was analyzed and confirmed by ¹H NMR,¹³C NMR and HRMS.The UV absorption spectrum and fluorescence emission spectrum of the probe were measured in the presence of different ions.It was found that the fluorescent probe NAFH had a specific response to hypochlorous acid.The anti-interference ability,detection limit,applicable p H range,response time,visualization application,cytotoxicity and biological application of the probe were studied for the detection of hypochlorous acid.Experiments performed that the fluorescent probe NAFH can be recognized by the naked eye to detect hypochlorous acid,and the probe has great potential in biological application.