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Research And Application Of Reactive Small Molecule Fluorescent Probes Based On Fluoroboron (BODIPY) Fluorophores

Posted on:2019-03-02Degree:MasterType:Thesis
Country:ChinaCandidate:B LiFull Text:PDF
GTID:2351330548958360Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Organic small molecule fluorescent probes are an effective molecular tool,and it are often used in molecular recognition and optical imaging because of their high sensitivity,specificity,rapid response,and simple technique,thus providing direct and quantitative information on the location and quantity of biomolecules Visualization and dynamic information.In addition,changes in the microenvironment are localized and monitored by taking full advantage of the spectral properties of molecular fluorophores.BODIPY dyes tend to be strongly UV-absorbing,emit relatively sharp fluorescent small molecules with high quantum yield peaks.At the same time,its polarity and p H change in microenvironment are relatively stable under physiological conditions.Therefore,modification of the fluorophore structure can change the fluorescence characteristics of the fluorophore.In this paper,Five organic small molecule fluorescent probes were designed and synthesized by the modification of BODIPY fluorophore.All the probe structures were confirmed by1H-NMR,13C-NMR and HRMS etc.Fluorescent molecular probes were used to detect small molecules.The information was tested by UV spectrophotometer and fluorescence spectrometer.1.The hydrazine reaction functional group is connected to 3-position of BODIPY.by nucleophilic substitution reaction,Which was finally used to synthesize two small molecular target probe(the fluorescent probe HP1 and HP2).The molecular probe in the phosphate buffer saline(PBS = 7.4)showed high selection,highly sensitive recognition of hydrazine molecules.When hydrazine molecules was added,the fluorescence intensity increased significantly.Hydrazine hydrate molecular probes can be used to double channel recognition of hydrazine molecules by the naked eye and fluorescence.2.An OFF-ON fluorescent probe was synthesized,whose receptor of the hydrazine group was conjugated to 3-position of BODIPY for formaldehyde recognition.It selectively recognizes formaldehyde in a buffered solution(PBS = 7.4)and ultimately effect OFF-ON of signal changes when formaldehyde was added.The small molecule of formaldehyde probe can be detected with high sensitivity and high selectivity in aqueous solution.In the presence of formaldehyde,the fluorescence intensity of the molecular probe rapidly increases,Which eventually inhibit the PET effect and realize the selective recognition of small molecule formaldehyde.3.Two hypochlorous molecular probes was designed and synthesized,Which introduced two different reactive functional groups based on Knoevenagel reaction.The selectivity of the three fluorescent probes can be tested in aqueous buffer solutions in which the fluorescence changes sharply with the addition of Cl O-in a buffered solution(PBS = 7.4).The fluorescent probe exhibits excellent sensitivity and selectivity to hypochlorous acid in aqueous solution.
Keywords/Search Tags:Fluorescent probe, Boron dipyrromethene, PET, Formaldehyde, Hypochlorous acid
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