Synthesis And Application Of Fluorescent Probes Based On BODIPY And Quinolone

Fluorescent probes are recently an effective detection method that can convert the chemical information generated by the interaction between different substances into fluorescent signals.In the last decads,development of fluorescent probes have gradually replaced traditional detection technologies and become crucial part in the field of medical and modern science,such as:biological testing,clinical medicine,drug screening,materials science,analysis,environmental chemistry,etc.Recently,fluorophores such as fluorescein,phenothiazine,quinoline,quinolone,coumarin,fluoborazole,rhodamine etc.have been developed for selective signalling of chemical and biological samples because of their high quantum yield,good stability and high solubility.In this paper,we have constructed fluorescent probes consisting of BODIPY and quinolone fluorophores for signaling of nitric oxide,biothiols and phosgene which are harmful to the human body as it is stated in the research objects.The concrete contents are as follows:In the chapter 2,we have developed fluorescent probe 8-HB,with BODIPY as a fluorophore and 8-substituted hydrazine as an active site for the detection of NO.The probe 8-HB can react with NO/O2 to generate fluorescent dehydrazinated BODIPY accompanied by 8-azide BODIPY.8-HB shows high selectivity and sensitively for NO over RNS,ROS and ions.This proved that the three compounds of 60 ?M,the cell viability is as high as 80%,and the exogenous and endogenous NO in cells can be detected.In the chapter 3,we have compared their sensing performance of two fluorescent probes,o-Pah and o-Pha,which are two ortho-aminohydroxy(3',4' or 4',3')phenyls at meso position of BODIPY as the reactive sites for phosgene.The probe with-o-(4'-amino-3'-hydroxyl),o-Pha,exhibits better sensing performance over the probe with o-(3'-amino-4'-hydroxyl),o-Pah,for instance,lower background fluorescence to a lower limit of detection(LOD),and more rapid response.The sensing mechanism was demonstrated.Based on results from comparison investigations,a red-fluorescence probe o-Phae has been constructed through extending 3,5-conjugation of BODIPY as a fluorophore and o-aminohydroxy(4',3')phenyl as the recognition site.The probe o-Phae displays high sensitivity to triphosgene(LOD=0.88 nM)and high selectivity toward phosgene over relevant analytes including nitric oxide,nerve agent mimics and acyl chlorides.Furthermore,a facile test strip for phosgene was fabricated by immobilizing o-Phae in a polyethylene oxide membrane for rapid and selective detection of phosgene in gas phase.In the chapter 4,a longer conjugated chain and colorimetric fluorescent probe BODIPY-1 has been synthesized that was found to be sensitive to the presence of phosgene(LOD of 68 nM)and sulfonyl chloride with naked eye visible color changes from blue to pink and fluorescence intensity enhancements.Furthermore,a facile testing strip was fabricated by immobilizing BODIPY-1 on a polyethylene oxide membrane for real-time selective monitoring of phosgene in gas phase.In the chapter 5,we have constructed five different types of quinolone-based fluorescent probes(QB-1,QB-2,QB-3,QB-4 and QB-5)for the detection of biothiols.QB-5,a red fluorescent probe,dispalys the best sensing performance such as high selectivity and good sensitivity for Cys(LOD=0.17 ?M)and GSH(LOD=0.46 ?M_,and can achieve to discrimination between Cys,GSH and Hcy through two different fluorescence channels.For instance,a turn-on fluorescence centred at 420 nm for Cys,ratiometric fluorescence at 643 nm/537 nm for GSH and no response for Hcy.Furthermore,QB-5 can be used to detect endogenous Cys and GSH in two fluorescent channels in living cells.