| Anions widely exist in nature,and play an extremely important role in many fields such as environmental science,clinical medicine,biology and chemical production.However,high concentrations of toxic anions in the environment(such as cyanide ions,fluoride ions)will affect nature.The environment and human health cause great harm.Compared with traditional anion detection methods,fluorescent probes have excellent properties such as high sensitivity,high selectivity,and fast response.They are widely used in the detection of metal ions,anions,small organic molecules,and large biological molecules in living organisms.Therefore,the development of artificially synthesized fluorescent probes for the specific and highly sensitive detection of anions has good application prospects in the field of supramolecular chemistry.BODIPY fluorescent dyes,due to its unique photoelectric properties,such as strong fluorescence emission in the visible near infrared region,high fluorescence quantum yield,long fluorescence lifetime,and excellent chemical stability,have attracted much attention in supramolecular chemistry.Also,it has a wide range of applications the fields of self-assembly materials,organic semiconductor materials,biological fluorescent dyes and fluorescent switches.In recent years,more and more scholars have paid attention to BODIPY derivatives and it become one of the current research hotspots.Therefore,designing and synthesizing novel BODIPY fluorescent probes that specifically recognize anions has important significance in the field of biological probes.In this paper,based on the previous research of the research group and literature research,we designed and synthesized two series of BODIPY-based novel fluorescent probes by using fluoroborodipyrrole as a fluorophore.These probes can be used for highly selective detection of cyanide and fluoride ions,respectively.The UV-visible spectrum,fluorescence emission spectrum,1H NMR titration,mass spectrometry and other experiments have been investigated to confirm the detection mechanism of fluorescent probes for related anions.The potential applications of probes such as reversibility,aqueous solution,and test paper were also discussed.Secondly,through the nucleophilic substitution reaction between 3,5-dibromofluoroborodipyrrole and phenylacetonitrile,the trifluoroboron dipyrrole derivative R1 containing an activated CHCN group at position 3 was successfully designed and synthesized.A potential intramolecular CH...F hydrogen bond was founded to further enhance carbanion stability.Through ultraviolet absorption and fluorescence emission spectroscopy studies,it was found that the fluorescent probe has high selectivity,high sensitivity,reversibility for cyanide ions,and detecting cyanide ions in aqueous solutions.At the same time,the minimum fluorescence detection limit in 70 % aqueous solutions is up to 148 n M.In addition,the fluorescent probe R1 can also be used for sensitive and reversible detection of cyanide ions in test strips.Finally,using 4-hydroxyfluoroborodipyrrole as the fluorophore and tert-butyldiphenylsilyl(TBDPS)as the protective group for the active hydroxyl group,a novel fluorescen BODIPY-based R2 containing silicon-oxygen bond by a fluoride-triggered release reaction was designed and synthesized.The fluorescent probe R2 was characterized by 1H NMR,13 C NMR,and high-resolution mass spectrometry.Spectral experiments showed that after the fluorescent probe interacted with fluoride ion,a new absorption peak appeared at 605 nm in the ultraviolet absorption spectrum.The needle solution changed from orange to blue;the maximum emission peak at 514 nm in the fluorescence emission spectrum decreased,and the fluorescence color changed from green to fluorescence quenching.In addition,the naked eye detection of fluoride ions in test paper is also achieved. |
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