The Design And Synthesis Of Several Fluorescence Probes And Performance Research

With the rapid development of industry, more and more toxic and harmful pollutants are brought about, such as heavy metals, pesticides, organic compounds, et al. Analyzing and monitoring the trace pollutants becomes more and more important in the fields of environmental science and engineering. Take advantage of high sensitivity and selectivity, fluorescence analysis was developed, and fluorescent probe has been widely applied in environmental analytical chemistry.In this thesis, new fluorescence probes are not only simple but also excellent in selectiveity, stability and sensitivity, which were designed and synthesized. Then the analytical properties and applications of the fluorescence probes were studied. Three different fluorescence probes prepared in the experiment were studied.(1) N-(pyridyl-2-methyl)-4-bromo-1,8-naphthalimide (PMAN) was synthesized and its fluorescence properties were studied in tetrahydrofuran solution. Fluorescence intensity of PMAN decreased remarkably with the increasing of pH from 1.00~4.07. The effects of different metal ions on the fluorescence intensity were investigeted and the fluorescence intensity was only quenched by Fe3+. The linear equation(y=-10.31x+242.5) for Fe3+ determination was obtained with excellent relativity and the linear range was 1.0×10-5～2.0×10-7mol/L. The detection limit was 3.5×10-8 mol/L. The fluorescence probe was applied to determination of Fe3+ in water samples and the recovery was 96.1%-102.8%。(2) N-(diaminoethyl)-4-bromo-1,8-naphthalimide (DBN) was synthesized. Strong and stable room temperature phosphorescence (RTP) signals were observed in the ternary system of DBN,β-cyclodextrin and cyclohexane. The maximum excitation and emission wavelengths were at 347 and 572 nm, respectively. The concentration ofβ-CD, cyclohexane were investigeted. A good linearity between the RTP intensity and the concentration of DBN from 2×10-5 to 9×10-5mol/L was obtained with a minimum detection concentration of 6.7×10-7 mol/L. The RTP of DBN was sensitive to pH1.0~4.0. The method was applied to determination of DBN in water samples and the recovery was 98.9%~102.3% with a relative standard deviation less than 1.4%. The fluorescence and phosphorescence properties of DBN were obviously different owing to the mechanisms of them were different.(3) Phenylboronic acid derivatives are known to form reversible complexes with polyol compounds. The reaction product of 2-formaldehydeyl-phenyboronic acid and 2-aminofluorene was not the compound which designed according to experiment. The course of this result might be the reaction solvent was not satisfactory.