Design,Synthesis And Application Of Anthracene Derivative Fluorescent Probes With Aie Properties

Fluorescent probes are used as an important optical sensor and have been widely used in chemical,physical,biological,medical and other fields.It has been favored by scientists,because of its high sensitivity,good selectivity,and ease of use.Usually,people use Rhodamines,Cyanine dyes,Coumarins,BODIPY and other fluorescent molecules as fluorescent probes,but these traditional fluorescent probes often have application limitations.The probe of traditional molecular have strong fluorescence in the solution state,but their fluorescence is significantly weakened or even completely quenched in the aggregated or solid state.The phenomenon of aggregation-caused quenching（ACQ）has limited the application of traditional fluorescent molecules.For example,in the detection of biomolecules,these fluorescent molecules are used as probes to bind to the target and aggregate on the surface of the analyte.The occurrence of such aggregation can cause the fluorescence intensity to decrease or even quench,which seriously affects the accuracy of the analysis results.However,the appearance of aggregation-induced emission（AIE）phenomenon provides a new strategy to solve the problem of ACQ from traditional organic fluorescent molecules.AIE molecules have no fluorescence in solution or in a dispersed state,but emit strong fluorescence in an aggregated or solid state.Due to the unique properties of AIE molecules,more and more AIE molecules have been developed and applied in the fields of ion detection,biomolecule detection,and biological imaging.Based on 9,10-divinylanthracene,a series of AIE materials have been designed and synthesized for ion detection,biomolecule detection and biological imaging.The specific research content is as follows:1.Novel PSMA-coated on-off-on fluorescent chemosensor based on organic dots with AIEgens for detection of copper（II）,Iron（III）and cysteine.According to the reported methods,we have prepared 9,10-distyryl anthracene（DSA）molecules with AIE properties.Then,the DSA molecules were coated by the polymer styrene-co-maleic anhydride（PSMA）which have the self-assembly properties.As binding groups,the carboxyl groups on the surface of the DSA dots can interact with Cu²⁺and Fe³⁺.When DSA dots combined with metal ions,its fluorescence intensity decreased.When the strong copper ion chelator cysteine were added to the system,the fluorescence intensity of DSA dots were restored.Using above principle,the detection of specific metal ions and cysteine from"turn-off"to"turn-on"fluorescence is achieved.2.Fluorescence detection of protamine,heparin and heparinase II based on a novel AIE molecule with four carboxyl.A new DSA（Distyryl-anthracene）derivative with four carboxyl groups was designed and synthesized.This molecule exhibits aggregation-induced emission property（AIE）.The protamine can directly induce the aggregation of probe,which caused by electrostatic attraction.In this way,the turn-on detection of protamine is achieved.When heparin appears,the probes will be redisperse in solution,which causes a decrease in fluorescence intensity.Besides,this method also shows good selectivity and sensitivity.After hydrolyzing heparin by heparinase,the probes rebind with protamine and the fluorescence enhance.With the AIE character,a convenient and sensitive fluorescent probe for the detection of protamine,heparin and heparinase has been developed.3.Synthesis and application of mitochondrial fluorescent probes based on aggregation-induced luminescence properties.Triphenylphosphine salt（TPP）is widely used as a mitochondrial targeting group,we used the DSA molecule as the luminescent core and modified the triphenylphosphine salt group（TPP）at both sides of the fluorescent probe to obtain the fluorescent probe DSA-PPh₃.We use the hydrophobicity of the molecular structure of DSA-PPh3 to prepare fluorescent nanoparticles and use them to achieve mitochondrial fluorescent labeling.By comparing with the commercial mitochondrial dye Mitotracker Red,we found that the probe has good imaging ability,better resistance to photobleaching and stability.In addition,we studied the effects of mitochondrial membrane potential changes on probe imaging through drug regulation.Experimental results show that DSA-PPh₃nanoparticles have good stability and are potential mitochondrial fluorescent probes.