Synthesis And Cell Imaging Applications Based On Phenothiazine Derivatives Fluorescent Probe

Fluorescent probes are widely used in environmental pollutant detection,biomolecule and ion recognition and so on,which is ascribe to their advantages of high sensitivity,fast response,low cost,and real-time monitoring.However,there existed problems like short-wavelength absorption and emission,small Stokes shift,poor solubility,ACQ phenomenon and poor cell membrane penetration.These problems inhibited their further applications in the biological field.In view of this,fluorescent probes of phenothiazine rhodanine and cationic phenothiazine quinoline were synthesized to explore their optical properties and their ability to identify and detect anions,and for cell biological imaging.Due to the wide application and high toxicity of cyanide,a novel fluorescent probe PTZCN based on phenothiazine and rhodanine was designed and synthesized.Its structure was characterized by ¹H NMR,¹³C NMR,infrared spectroscopy and mass spectrometry.The TICT phenomenon and the AIE effect were found on the probe with Stokes shift as high as 209nm.It can detect and recognize CN^-in nearly pure water,whose emission wavelength was 689 nm and the detection limit was 94.18 n M.This detection limit was far below the WHO regulations with in drinkable water?1.9?M?.The Job curve showed that the binding ratio of CN^-to the probe PTZCN is 1:1.The ¹H NMR showed that CN^-destroyed the conjugate structure of the molecule and the intramolecular charge transfer?ICT?by attacking the double bond on the vinyl group.In this way,the fluorescence was quenched.In addition,the PTZCN can be prepared as a probe test paper for the detection of CN^-in water,and can also be used in cytoplasmic imaging.Hypochlorite ion,as an important active oxygen species,plays a vital role in human life activities such as aging and immune system.The imbalance of hypochlorite content can cause inflammation and cardiovascular diseases.In this thesis,phenothiazine was used as electron-rich electron-donating group and cationic quinolinium salt as electron-withdrawing group.A fluorescent probe with"turn-on"effect was designed,which was characterized by infrared spectroscopy,¹H NMR,¹³C NMR and mass spectrometry.The PTZQL can specifically recognize Cl O^-in almost pure water with a wide p H range?p H=6-10?.It also had a fast response time?t=20 s?and a low detection limit of 34.4 n M.Mass spectrometry analysis found that hypochlorite can oxidize the sulfur on the phenothiazine group into a sulfoxide structure.Then the molecule was cleaved into the product of the aldehyde group structure with a double bond interrupted.The fluorescence was enhanced with"turn-on"effect.The PTZQL was charactered with good cell penetration and low toxicity,which proved its potential in imaging of exogenous hypochlorite of cells.