Synthesis And Properties Study Of Fluorescent Dye BODIPY And TPT Derivatives

Recently,fluorescent chemical sensors have been widespread used for the detection of small molecules,cations,anions and pH due to their advantages such as higher selectivity and sensitivity,lower cost and convenience.Then,organic fluorescent dyes have become an important material for designing fluorescent probes with their simple synthesis,diverse structures,and particularly strong plasticity.?1?In most fluorescent chromophore,BODIPY,which is a common fluorescent dye,is widely studied because of its high fluorescence quantum yield,low cytotoxicity,high molar extinction coefficient and strong modification.However,the shortcomings of low synthetic yield and the short emission wavelength of the fluorophore itself,hindered its development.Therefore,shortening the synthetic steps,increasing the yield,and red-shifted the emission wavelength become the key and difficult point of designing BODIPY-based fluorescent probes.Thereupon,BODIPY is used as a fluorescent group in this paper,and different recognition groups have been introduced with short synthesis steps and high yields,then two BODIPY fluorescent probes dppy-BODIPY and Ch-BODIPY were synthesized and characterized by ¹H NMR,¹³C NMR.In just one step,BODIPY fluorescent probes with recognition groups dppy and Ch can be obtained while synthesizing the BODIPY nucleus.dppy-BODIPY was obtained at a yield of 40%,and was produced by recrystallization,which avoids the trouble of column chromatography of compounds containing multiple nitrogen atoms.Besides,the methyl group was introduced at the 1,3,5,7 position and the ethyl group at the 2,6 position is helpful the red-shifted emission wavelength.Because of the excessive addition of anisaldehyde,the target probe molecule?Ch-BODIPY?was obtained as a by-product during the synthesis of Ac-BODIPY,and the reaction process was discussed.?2?As a member of organic fluorescent molecules,fluorescent molecules with aggregation-induced emission?AIE?properties have the advantages of easy structure control and strong designability,but effectively overcome the shortcoming of conventional fluorescent molecule aggregation-induced quenching?ACQ?.It has attracted widespread attention,and new types of molecular probes with AIE properties are also emerging.Hence,it is a hot research topic to design and synthesize novel molecules with AIE property and apply them to the fields of biological imaging and molecular ion recognition.Accordingly,a malononitrile AIE molecule Cy-TPT with D-?-A configuration was designed and synthesized in short steps,and characterized by¹H NMR,¹³C NMR and ESI-MS.Its properties were studied by UV-visible/fluorescent spectrophotometry.The results show that the Stokes shift of Cy-TPT can reach more than 120 nm,and it shows good AIE performance in a variety of solvents with different ratios.