Synthesis And Application Of Novel BODIPY Fluorescent Dyes

In recent years,the fluorescent dye has shown the unprecedented utilization potentiality,such as optical material,metallic ion detection,PH test,fluorescence probe,environmental sciences,analytical chemistry,cell imaging,tracer,protein or DNA label and new solar battery.It is of great significance to develop fluorescent dyes with excellent spectral properties.Among the many fluorescent dyes,Fluoride(BODIPY)fluorescent dyes have attracted much attention.BODIPY fluorochrome is equipped with many good physical and actinology properties,including narrow and sharp absorption and emission peak,higher fluorescence quantum efficiency,low damages to living body,insusceptible to effects of environment and PH and structure easily decorated.Given these prior properties,the BODIPY fluorochrome has been widely used in fluorescence probe,DNA and mark of protein,photodynamic therapy and dye-sensitized solar cell.However,the classical BODIPY dye also has some disadvantages,such as little displacement of stokes,fluorescence easily quenched in solid state,short waves of absorption and emission,have limited application and development of BODIPYfluorescent dye.(1)By selecting the phenothiazine group with strong electron donating ability as electron donor,Nitrogen,oxygen,fluorine and boron hybrid as electron acceptor.A series of novel fluoroboron fluorescent dyes(9 in total)were designed and synthesized.The structure was characterized by 1H NMR,13 C NMR,HRMS and XRD.(2)Through the test of spectral properties of UV absorption spectrum,fluorescence emission spectrum,a series of new dyesin different solvents(ethanol,dichloromethane,tetrahydrofuran,acetonitrile and acetonitrile: PBS(1:1;v/v)system),obtained the performance parameters,and the influence of solvent polarity on the spectral properties and effects of different substituent groups on spectral properties is summarized.The relationship between the molecular properties and the spectral performance is also discussed.After detection,series of fluoro boron dyes have a long emission wavelength(567-679 nm)and a larger stokes shift(144-223 nm)both in polar and non-polar solvents.In addition,unlike the classic BODIPY dyes,the series of new fluoroboron dyes still have strong fluorescence properties in solid state,and thus have broad application prospects.In order to overcome the shortcomings of poor water solubility of these dyes,the hydrophilic group sulfonic acid group was introduced into the dye molecular structure,and the water-soluble fluoroboron dye 5A was synthesized.The dye has a solubility in pure PBS buffer of up to 1.6 mg / m L and has good water solubility.In addition,the molecule is also easily aggregated in the cavity of fetal bovine serum albumin(BSA),which makes the fluorescence enhanced and thus can be used to detect the BSA content in the solution.(3)With this type of new dye molecule 5H as the parent,this paper also designed and synthesized a new type of fluorescent probe molecules,respectively,for the detection of air pollutants thiophenol and selenocysteine.The test proves that this probe has a good result in test and this probe can test thiophenol in buffer solution,serum,cell and on filter paper and all possess high sensibility and low detection limit(The theory of detection limit has decreased to.4n M which is the lowest experimental detection limit of reported tested thiophenol so far).In addition,the probe molecules,but also can achieve the detection of intracellular thiophenol,which has important bio-application prospects.