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The Development Of A Dual-channel Near-infrared PH Fluorescent Probe And The Development Of Asymmetric Aza-BODIPY With An Absorption Wavelength Greater Than 700 Nm

Posted on:2022-05-09Degree:MasterType:Thesis
Country:ChinaCandidate:C LiFull Text:PDF
GTID:2491306548965859Subject:Organic Chemistry
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This article briefly describes the application of BODIPY/aza-BODIPY fluorescent dyes in the detection of cations.The N1,N2-bis(4-(dimethylamino)phenyl)oxalamide(DNOXA)and furyl-substituted symmetric aza-BODIPY and furyl-substituted asymmetric aza-BODIPY were also synthesized,in which DNOXA can detect H+.The first chapter briefly describes the design and synthesis method of BODIPY/aza-BODIPY fluorescent dyes,as well as the research of its functional application.It includes the application of various cations such as hydrogen ion,copper ion and mercury ion detection,as well as the detection of BODIPY/aza-BODIPY fluorescent dyes reported by our research group since 2013.Specifically,it includes the synthesis,performance and application of amide derivatives for detecting hydrogen ions,and the preparation of unsymmetric BODIPY/aza-BODIPY fluorescent dye derivatives,ect.In the second chapter of this article,N1,N2-bis(4-(dimethylamino)phenyl)oxalamide(DNOXA)was synthesized according to the reported method of amide synthesis,and the properties of DNOXA were studied for the first time.Compared with N1,N2-di-p-tolyloxalamide(DMOXA),the ability of DNOXA to detect hydrogen ions indicates a significant difference between the presence of the substituted dimethylamino group with the amide group and between the dimethylamino group alone.DNOXA containing dimethylamino can be used as a pH-responsive fluorescence sensor to detect hydrogen ions.At the same time,contrary to the protonated blue shift of traditional pH fluorescent probes,DNOXA exhibits a significant red shift due to the formation of a conjugated system.In addition,the probe can be used to locate lysosomes in MCF-7 human breast cancer cells,indicating that it has potential use in locating lysosomes.Finally,BF2-dikaryon compound was synthesized by the reaction of DNOXA and BF3·Et2O.However,due to the relatively unstable system,the species was not successfully isolated,which also encouraged us to further study the modification of BF2-dikaryon compounds in order to provide a series of stable compounds in the laboratory.In the third chapter,2-aminobenzothiazole was used as the starting material to successfully prepare a seven-membered ring compound,and 2-hydroxy-4-methoxybenzaldehyde and cyclohexenone were used as starting materials to successfully prepare unsymmetric BODIPY fluorescent dye derivative.The synthesized two compounds enrich the types of asymmetric BODIPY fluorescent dyes and lay a solid foundation for their future functionalization.In addition,furanyl-substituted symmetrical aza-BODIPY and furyl-substituted asymmetric aza-BODIPY were synthesized by Carreira synthesis method.Most of the absorption spectra are larger than 700 nm,which have excellent spectral characteristics and are expected to be used in commercialization.
Keywords/Search Tags:BODIPY, aza-BODIPY, fluorescent dye, DNOXA, pH
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