Synthesis And Photophysical Properties Of Tri-Pod Fluorescent Dyes Bearing Electron-rich Phenolic Derivatives

Because of its high sensitivity, fluorescence analyzing technology plays an important role inenvironmental science, medicine, pharmacy, and cellular biology. Among the most commonly usedfluorescent reagents such as fluoresceins, rhodamines, cyanine dyes and BODIPY compounds,BODIPY dyes bearing excellent emission and absorption wavelength, high molar extinctioncoefficient, high quantum efficiencies, good photostability, sharp intense absorption which can betuned easily etc, have attracted great attention in the last ten years.In this thesis, four kinds of phenolic compounds bearing electron-donating groups wereintroduced to cyanuric chloride to synthesize a series of intermediates, which were then used tosynthesize the corresponding BODIPY dyes. All these eight compounds haven’t been reported so far,and were characterized by1H NMR,13C NMR, IR, MS. The appropriate reaction conditions werefound through exploring the reaction sequence and the workup procedure.The optimized reaction conditions:(1) The displacement order of cyanuric chloride. First chlorine atom was substituted by phenoliccompounds which have electron-donating groups. And then, the second chlorine atom was substitutedby4-hydroxybenaldehyde.(2) DIEA was proved to be the best acid-binder in the process of intermediates synthesis.(3) The removal of DDHQ, the reductive product of DDQ, right after the end of the oxidationstep, favored the subsequent separation procedure greatly.Photophysical properties of the dyes indicated that:(1) The maximum absorption wavelength of the four dyes obtained here were influenced bysolvents slightly. In chloroform, the maximum absorption wavelength is504nm, wheras503nm incyclohexane and499nm in metanol were received respectively. And in the same solvent, themaximum absorption wavelength of the four dyes were the same. This indicated that the four kinds ofelectron-rich phenolic moieties used in the auxillary part did not affect the maximum absorptionwavelength of the fluorophore of the dyes either.(2) The four kinds of electron-rich phenolic moieties used in the auxillary part did not affect themaximum emission wavelength of the dyes either. (3) The fluorescence quantum yields of dyes showed that: the stronger electron-donating abilityof phenolic derivatives, the greater the fluorescence intensity.