Studies Of Synthesis And Properties Of Diarylethene Fluorescent Probes Based On Acylhydrazone-linker

Zinc ion is the second most abundant transition metal ion in human body.It plays an important role in many intracellular and extracellular physiological processes.In addition,excess zinc ion in environment will produce certain toxic effects on plants.Therefore,it is of great significance to quickly and inexpensively detect the concentration of zinc ion in human body and environment.Compared with emission spectrometry,high performance liquid chromatography,inductively coupled plasma mass spectrometry and other methods,fluorescence analysis has the advantages of high sensitivity,good selectivity,short response time,and no site limitation.Therefore,fluorescence analysis method has caused widespread concern in the ion detection.On the other hand,among different photochromic materials,diarylethene compounds are hot topics due to their good thermal stability,fatigue resistance,and fast response;acylhydrazones are more stable than ordinary Schiff bases and have a strong chelating ability.Therefore,they are used as linking groups not only simplify the synthesis step,but also improve the selectivity.Based on the above facts,the following four types of diarylethene derivatives with multiple responses were designed and synthesized.The specific research contents are as follows:In chapter 1,the method,mechanism and significance of ion fluorescence sensors were introduced.Besides,the research progress of photochromic materials and the acylhydrazone Schiff bases and the advantages of diarylethene derivatives were described.Finally,the main research contents of this paper were proposed.In chapter 2,a diarylethene derivative,DTIP-1O,containing imidazo[1,2-a]pyridine was designed and synthesized.Firstly,the fluorescence selectivity of sensor DTIP-1O to metal ions was studied.The results showed that it has specific recognition effect on Zn²⁺;then the colorimetric characteristics of the compound were studied.In chapter 3,the 1H-Indazole was linked to the diarylethylene through a acylhydrazones to form compound DTI-2O.In the UV test,the compound can not only selectively recognize CN^-and F^-,but also respond to OH^-.In the fluorescence test,this compound has a specific recognition of the cation Zn²⁺.In chapter 4,a novel diarylethylene derivative DTNA-3O containing naphthol was synthesized.In the fluorescence test,the compound had a solvent effect and selected different ions in different solvents.In tetrahydrofuran solution,the compound can specifically recognize Zn²⁺,while in acetonitrile,the compound can specifically recognize Al³⁺.In chapter 5,the imidazo[2,1-b]thiazole was introduced into the diarylethylene via a acylhydrazone to form a new compound,DTIT-4O,which selectively recognized Zn²⁺and Al³⁺in methanol solution.When Zn²⁺and Al³⁺were added,the color of the solution turned yellow-green and bright green,respectively.Furthermore,the complexation mechanisms of this compound with Zn²⁺and Al³⁺in methanol were different and verified by NMR and mass spectrometry.