Synthesis And Properties Of Aminophenylboronic Acid Pinacol Ester Derivatives

Organoboric acid has important applications in the field of chemistry.They are important reagents,catalysts and intermediates in organic synthesis.Compounds containing boric acid?BA?groups have a wide range of uses,which makes them one of the most widely studied and used chemical functional groups in biomedical applications.Compounds containing boric acid or boric acid esters are also very useful for Suzuki-Miyaura cross-coupling reactions and as molecular recognition sensors.Combining the two popular fields of organic synthesis and molecular recognition,based on the meta-and para-substituted aminophenylboronic acid pinacol ester,this paper synthesized 21 compounds containing organic boric acid or boric acid ester.In this paper,three types of phenylboronic acid pinacol ester derivatives were synthesized through a three-step experiment.A total of 21 such compounds were used.The first step of the experiment was based on the reaction of amino substituted phenylboronic acid pinacol ester with different aromatic aldehydes to generate 7intermediate Schiff bases containing the phenylboronic acid pinacol ester structure;Add diethyl phosphite to the resulting product to form 7 phenylboronic acid pinacol ester derivatives containing phosphonate substituents;the third step is to hydrolyze the phenylboronic acid pinacol ester derivative of the second step Phenylboronic acid derivatives,obtained 7 compounds containing boric acid structure.In addition,the compounds were characterized by ¹H NMR,¹³C NMR,IR,and MS to determine the target product.In this thesis,four meta-substituted phenylboronic acid pinacol ester compounds and the 3-aminophenylboronic acid pinacol ester synthesized in the second step were selected,and their fluorescence properties were investigated by fluorescence spectroscopy.The results show that,in addition to the nitro-substituted compounds,the other four compounds have higher fluorescence intensity in the solid state or the solution state.At the same time,the study also found that solvents of different polarities also had a certain effect on the fluorescence intensity of the compound.In the less polar organic solvents,the comparison order of the compound's fluorescence intensity is basically the same as the solid sequence,while in the more polar solvents,certain changes have occurred.Through fluorescence detection of the solution of dopamine?DA?and gallic acid,it can be found that the compound has a good recognition effect on dopamine and gallic acid.The results show that the compounds can be used for the detection of dopamine and gallic acid.