Synthesis And Property Study Of Fluorescent Sensors Based On Conjugated Skeleton Structure Design

Excessive volatile amines can cause environmental pollution and harm human health,so the design and synthesis of chemical sensors for volatile amines has been widely studied,with fluorescence sensors being an important one.Tetraphenylethylene(TPE)is a kind of fluorescent dye with aggregation induced emission property,which has simple molecular structure and easy to be functionalized.Its application has attracted much attention in chemical sensors.For sensors with TPE core,the chemical reaction between functional groups in the sensing material and amine compounds changes the structure of the sensor chromophore,causing significant changes in its fluorescence,which has the advantages of high sensitivity and specific recognition.Therefore,further exploring new response systems and tapping into the greater application potential of TPE is of great significance.In the first part of this thesis,we designed a solid state fluorescence sensor molecule,TBDQ,based on the TPE skeleton structure and its AIE characteristics,combined with colorimetric and fluorescence sensor performance.In the presence of amine,the quinone unit and amine in TBDQ molecule pass through Michael addition reaction,and the generated product changes the π-π conjugate structure inside the molecule through redox reaction and intramolecular rearrangement,thus producing TPE derivatives,reconstructing the TPE skeleton,and producing aggregated luminescence.In addition,the response of compound TBDQ to a series of amines was also studied,and it was found that the compound showed significant responses to both monoamines and diamines separately.In addition,the TBDQ compound can easily be loaded on the paper by soaking,and a portable sensor for detecting amine vapor can be prepared,which has the advantages of high sensitivity,low cost,and real-time detection.In the second part y,we designed and synthesized a new quinoline compound,2-(3,5difluoro-4-hydroxystyryl)-2-quinoline.Further investigation showed that this compound response to the acid,base and ions with UV visible and fluorescence spectroscopies changes,together with significant color changes which can be recognized by the naked eyes.Moreover,this compound also responsed to cationic cuprous ions.