Design And Synthesis Of A New Fluorescent Probe Based On Aggregation-Induced Emission(AIE)

In recent decades,the study of fluorescence probe based on Aggregation-Induced Emission(AIE)mechanism has greatly promoted the design and synthesis of AIE molecules.The AIE effect has been proposed and discovered in order to solve the phenomenon of Aggregation Caused Quenching(ACQ)of traditional fluorescent molecules and greatly expand the application range of fluorescent molecules.Currently,the AIE fluorescent molecules have played an important role in the fields of Chemo-sensors?Bio-sensors?Cell-imaging?Protein conformation study?Organic light-emitting diodes and photodynamic therapy.Although a large number of fluorescent probes based on different mechanisms have been reported,most of them require harsh reaction conditions and lack of specific selectivity.Therefore,the design and synthesis of a new type of high sensitivity and high selectivity of the fluorescent probe still need our efforts.In this thesis,we have tried a variety of methods to synthesize BODIPY-based fluorescent compound D4,such as Reimer-Tiemann reaction of chloroform and strong alkali system,magnesium chloride catalyzed paraformaldehyde system and duff reaction system of urotropin.Based on this,we finally chose the method of this article to synthesize.We try to chloromethylate the p-hydroxybenzaldehyde first,then hydrolyze the hydroxyl group obtained from the hydrolysis to its own hydroxyl group to obtain the A3,with A3 as the aldehyde group bodipy after deprotection,which will be linked to the methyl hydroxyl oxidation to D4.And then on the basis of D4 plus different intermediates to form carbon-nitrogen double bond to get the final product.Fluorescent probes of this type contain hydrazone-like molecules with unsaturated carbon-nitrogen double bonds and adjacent hydroxyl groups.Fluorescence experiments show that the probe has a recognition effect on copper ions.The coordination of the probe molecule with copper ion changed the fluorescence property after the addition of H2S,which indicated that the probe molecule could recognize H2S on the basis of copper ion coordination.