Synthesis And Application Of BODIPY And Flavonoids Fluorescent Probe

Fluorescent dyes are a popular topic in the fields of chemistry and biology for the past few years,among which organic small molecule fluorescent probes have been widely used in many fields such as ion recognition,cell imaging,fluorescent labeling and photodynamic therapy.Currently,the common small molecule fluorescent dyes include coumarins,imidazoles,fluoresceins,rhodamines,naphthalimides,cyanines,flavonols and fluoro-boron dipyrrolidine(BODIPY),etc.Flavonol is a natural drug molecule with good biocompatibility;BODIPY compounds have excellent photophysical properties,such as higher molar absorption coefficient,higher fluorescence quantum yield and better photophysical stability;Flavonol compounds,as a kind of natural product molecules,not only have good biocompatibility,but also have great application potential in fluorescence detection.In this thesis,new type of fluorescent probe with BODIPY and flavonol dyes as research object were designed and synthesized,and its application also were explored.The main work of this thesis includes the following two parts:Part Ⅰ: BODIPY skeleton asymmetry modification and its application in fluorescence detection.Nitro,aldehyde and substituted aryl were introduced into the BODIPY molecule,so that six new asymmetric BODIPY compounds were gained,Among them,compounds MN2 containing hydrazone group could realize the selective recognition of the copper ions.Part Ⅱ: Study on photocatalytic synthesis of flavonols by one-pot method and Synthesis,Application of BODIPY-Flavonol double fluorophore probe.In the presence of catalyst,visible light mediated,using oxygen as oxygen source instead of hydrogen peroxide,the experimental conditions of one-pot synthesis of flavonol were investigated,and the conversion of chalcone to flavonol was realized.In addition,a BODIPY-Flavonol double fluorophore probe HCBO,was synthesized to realize the conjugate linkage between the structure of flavonol and the structure of BODIPY.On the basis of the characterization of its fluorescence properties,the selective fluorescence detection of reactive oxygen species and active nitrogen species was explored,revealing its broad biological application prospect.