Synthesis And Properties Of Novel Fluorescent Probes For Hypochlorous Acid

Hypochlorous acid(HOCl)is widely used in daily life and industrial production.However,the residual HOCl in the water can cause water pollution and the existence of potential harm to human health.In living organisms,HOCl plays a pivotal role in physiological process.But,once its content is beyond the normal physiological level,it will cause a series of disease.The detection of HOCl in environmental samples and organisms has become such an important issue that the development of new,fast,sensitive and selective fluorescent probes for HOCl is of great significance and application value.In this thesis,five novel HOCl fluorescent probes were designed and synthesized based on fully using the molecular fluorescent sensor principle of intramolecular charge transfer(ICT).They can be used for the detection of HOCl in both environmental samples and biological system,respectively.Two cases of ultrasensitive HOCl fluorescent probe,NDMTC and Lyso-NDMTC were synthesized by using naphthalimide as fluorophore and thiocarbamate as recognition receptor.The probe NDMTC has high sensitivity and selectivity to HOCl and can be used to rapidly identify HOCl in a wide pH range.In addition,it can be used for the detection of HOCl in environmental samples as well and can distinguish between breast cells and breast cancer cells,which successfully achieved two-photon fluorescence imaging of the endogenous HOCl in cells and mice.The targeted probe Lyso-NDMTC,which based on the probe NDMTC,achieves the detection and fluorescence imaging analysis of HOCl in lysosom of the liver cancer cell.A long wavelength fluorescent probe TCF-OCl for HOCl was synthesized by modification TCF.There is an obvious color change before and after the reaction with HOCl(from light yellow to red).TCF-OCl can rapidly detect HOCl by absorption spectrometry and fluorescence spectrometry.The probe TCF-OCl has good selectivity and water solubility which is successfully applied in the detection of HCIO in environmental samples.The maximum emission wavelength of the probe is at 610 nm,and it can be used for detecting HOCl in macrophage by fluorescence imaging.A ratiometric fluorescent probe AETU-HOCl was synthesized with a recognition receptor of diethylamino-thiourea.The emission peak of AETU-HOCl is centered at 533 nm and it blue shiftes to 473 nm after adding HOCl.Probe AETU-HOCl has excellent selectivity,and keeps stable when other higher concentrations of analytes are added.It can quickly identify HOCl in a wider range of pH and can be used for the detection of HOCl in environmental samples.AETU-HOCl can be used for the detection and analysis of HOCl in environmental samples and achieve ratio fluorescence imaging analysis of intracellular exogenous and endogenous HOCl.A colorimetric fluorescent probe BTAT for the detection of HOCl was synthesized with a recognition receptor of phenylboronic acid.BTAT has great solubility in water and selectivity.It can detect HOCl rapidly by absorption spectrometry and fluorescence spectroscopy.And,BTAT can be available for detecting HOCl in environmental samples and cell nucleus.The above results show that the five novel hypochlorous acid fluorescent probes not only can effectively detect HOCl in environment samples and biological system,but also laid the theoretical foundation for hypochlorous acid fluorescent probes and the development of probes for other environmental pollutants.