Synthesis And Photophysical Property Of Tri-Pod BODIPY Fluorescent Compounds Bearing Phenolic Derivatives

In rescent years, BODIPY(borondipyrromethene) fluorescent structures have got rapiddevelopment as higher fluorescence quantum yields and molar extinction coefficient, the stableoptical properties, good optical stability, molecular structure is easy to modify etc, four novel trupodBODIPY fluorescent compounds bearing phenolic derivatives were synthesized based on thecorresponding four intermediates obtained from the nucleophilic substitution of cyanuric chloride. Allthe eight compounds were characterized by1HNMR,13CNMR, IR, MS, and were not reported so for.First，the appropriate reaction conditions were found through exploring the reaction sequence,molar ratio and the addition methods.The optimized reaction conditions as follows:(1) The displacement order of cyanuric chloride. First, chlorine atom was substituted by phenoliccompounds. And the second chlorine atom was substituted by4-hydroxybenaldehyde; And the molarratio of the reactants was1.0:0.9:1.3.(2) DIEA was the better choice as as acid-binder during the process of intermediates synthesis.(3) Tendam reaction were adopted to fulfill the diethylamine displacement of the third chlorideand boro complexation process in one pot.(4) Proper eluents and separation conditions were found for the workup procedure of thesynthetic dyes.Next，analyses of the UV-Vis and fluorescence spectra of the dyes obtained in this paper showedthat:(1) The maximum absorption wavelength of these dyes were influenced by solvents slightly. Andin the same solvent, the maximum absorption wavelength of the four dyes were the same. Themaximum absorption wavelength in methanol, cyclohexane and chloroform were499nm,503nm,504nm respectively.(2) The four kinds of phenolic moieties used in the auxillary part affected the maximum emissionwavelength of the dyes slightly.(3) Relatively higher molar extinction coefficient and fluorescence quantum yields of the dyeswere found.