Synthesis And Performance Study Of Fluorescent Probes Based On 2’-Hydroxy Chalcone Derivatives

2-Hydroxychalcone is a fluorophore with aggregation-induced emission and excited-state intramolecular proton transfer properties.It has the advantages of simple synthesis,easy availability of raw materials,and good fluorescence properties,and is widely used in the synthesis of fluorescent probes.In this paper,using 2-hydroxychalcone as the structural skeleton,through appropriate structural modification,four fluorescent probes were designed and synthesized,and the fluorescence recognition performance of the probes was investigated.1.Probe DNBS-H was synthesized with 2-hydroxychalcone as the parent structure.The probe DNBS-H can recognize GSH/Hcy/Cys in DMSO/Tris（v:v=8:2,Tris 10 m M,p H=8.4）solution with high sensitivity selectivity and a large Stokes shift（>110 nm）.DNBS-H has low cytotoxicity and can be used to image GSH in living cells.2.The compound 2-2 obtained by the aldol condensation reaction reacted with2,4-dinitrofluorobenzene to give the probe DNBS-S.The probe DNBS-S displays weak fluorescence in DMSO/HEPES（v:v=8:2,HEPES 10 m M,p H=8.7）solution.The fluorescence emission increased greatly upon addition of HS^-DNBS-S has high selectivity to HS^-and is suitable to be used within alkaline p H range.Through cell imaging experiments,the probe DNBS-S can detect HS^-in living cells.3.The probe HCA-M was synthesized.When Hg²⁺was added,Hg²⁺reacted with the probe and caused removal of the thiocarbonate unit,which resulted in releasing of the fluorophore 2-2.The probe HCA-M realizes specific recognition to Hg²⁺in THF/PBS（v:v=3:7,PBS 20 m M,p H=8.0）solution.It has the advantages of long emission wavelength,high sensitivity,strong anti-interference ability and low detection limit(3.97×10^-5M).4.The probe HCA-P was synthesized.The probe HCA-P can recognize F^-in THF/PBS（v:v=3:7,PBS 20 m M,p H=8.0）solution using the characteristic of F^-induced silicon-oxygen bond cleavage,which results in releasing of the intermediate HCA with“AIE+ESIPT”characteristics.HCA-P has the characteristics of good stability,high sensitivity,specific recognition and low cytotoxicity.