Design And Synthesis Of Fluorescent Probes For Detecting Thiophenols/thiol And Their Application

Fluorescent probe technology,which with high sensitivity,high selectivity,low detection limit in the fields of biological detection,environmental analysis,and medical diagnosis.Thiophenol is a class of small molecule compounds widely used in organic synthesis for the preparation of various chemical products,such as agrochemicals,pharmaceuticals and other industrial products.Thiophenol is high toxic compounds that affect aquatic organisms and animals.Prolonged exposure of organisms to high concentrations of thiophenol liquid or vapor can cause a range of health problems,including various central nervous system damage,respiratory disorders,muscle atrophy,and death.Cysteine is one of the most abundant small molecule biothiols in the cell.Because of its unique redox properties,it can regulate the redox balance in living organisms,making them have a unique position in human health and disease.Therefore,it is of great scientific significance and application to design fluorescent probes for detecting thiophenol or for detecting Cysteine with excellent sensitivity,selectivity,and rapid response.In this paper,three types of chalcone fluorescent probes were designed and synthesized,two kinds of2,4-dinitrophenyl-chalcone probes were used in cells,and two chalcone fluorescent probes were used in seawater samples to detect thiophenol,one type of fluorescent probe complex for the detection of cysteine.This article is divided into three chapters:1.Design and synthesis two fluorescent probes（probe-KCP1 and probe-KCP2）detection of thiophenol based on chalcone luminophores in this chapter were confirmed by ¹H NMR,¹³C NMR,and mass spectrometry.The probe-KCP has a higher selectivity for thiophenols than other amino acids and common metal ions.The linear correlation between the fluorescence intensity and the concentration of thiophenol in the concentration range of thiophenol ranging from 0 to 15μM.The detection limit of the probe-KCP1was 28 nM（R²=0.9946）.The detection limit of probe-KCP2 was 37 nM（R²=0.9934）.The above experimental results indicate that the probe-KCP has high sensitivity for the detection of thiophenol.The fluorescent probe has a Stokes shift of 130 nm and a response time of 30 min（KCP2:10 min）.These two probes can be used for the qualitative and quantitative detection of thiophenol compounds in vitro experiments water samples.In addition,the probe-KCP was successfully used for the detection of thiophenol in living cells.The probe is a highly selective,highly sensitive fluorescent probe for the detection of thiophenol that can be used to detect thiophenols in environmental and biological samples.2.Two fluorescent probes（probe-KCN1 and probe-KCN2）to detect of thiophenols were design and synthesis in this chapter.The structures were confirmed by ¹H NMR,¹³C NMR,and mass spectrometry.The experimental results showed that the detection limit of probe-KCN1 was 79 nM（R²=0.9915）,and the detection limit of probe-KCN2 was 96 nM（R²=0.9978）for detected thiophenols.The probe has high selectivity,and sensitivity to thiophenols are much higher than other.The probes were also successfully applied to seawater samples for the detection of thiophenol.When the concentration of thiophenol in the range of 1 to 10?（44）,exhibits an excellent linear correlation between the concentration of thiophenol and the fluorescence intensity.It can be used for the quantitative and qualitative detection of thiophenol in seawater.3.Designed and synthesize a safe Chalcone-based fluorescent probe for detecting cysteine in this chapter,which also achieves intracellular cysteine imaging.The structure of the intermediate products and the target compounds were confirmed by ¹H NMR,¹³C NMR,and mass spectrometry.The probe has a specific selectivity for cysteine,which is much higher than glutathione and homocysteine.Low cytotoxicity allows the probe to be applied to detect cysteine in cells.In summary,five kinds of fluorescent probes based on chalcone were designed and synthesized in this paper,which have a rapid response time,a low detection limit and low cytotoxicity.It has been applied to the detection and imaging of thiophenol in living cells and water samples,and the detection of cysteine in cells.