Design Of Near-infrared BODIPY Fluorescent Probe And Its Application In Selective Detection Of Nitroaromatics

It is become an increasing urgent need to devolpment a rapid and selective detection method for Explosives containing nitroaromatics and their residues,which have brought serious social problems to homeland security and environmental hazards.Owing to the advantages of high sensitivity,easy operation,realtime monitoring,and low background interference,developing near-infrared fluorescent probes for the detection of nitroaromatics have become research topics which are under strong spotlight.Based on the principle of inhibiting Intramolecular the photo-induced electron transfer process(PET)result in fluorescence enhancement,combined with density functional theory(DFT)calculation,8-(4-aminophenyl)-1,2,6,7-tetraphenyl fluoride Boron dipyrromethene was precisely designed and synthesized as a novel near-infrared BODIPY fluorescent probe molecule for selectively detection of picric acid(PA).In this dissertation,the main research contents are summarized as follows:The first part(Chapter 2)of this dissertation focuses on the design and synthesis of a new type of near-infrared BODIPY fluorescent probe.Starting from iminodiacetic acid,via esterification reaction,acylation reaction,condensation reaction with benzil,decarboxylation reaction,organic phosphoric acid-catalyzed reaction with aromatic aldehyde to obtain a series of 5-aryl substitution-2,3,7,8-Tetraphenyldipyrromethanes,then DDQ oxidative dehydrogenation,and in situ complexation of BF₃·OEt₂ in the presence of a base to generate BODIPY fluorescent probe.A series of synthetic work has been carried out for the target molecule of 8-(4-aminophenyl)-1,2,6,7-tetraphenylfluoroboron dipyrromethene,the corresponding structures were characterized by ¹H NMR,¹³C NMR,¹⁹F NMR,HRMS and X-single crystal diffraction.The second part(Chapters 3)of this dissertation focuses on DFT calculation of BODIPY molecules and nitro-containing compounds,which shows has a good math in energy level between 8-(4-aminophenyl)-1,2,6,7-tetraphenylfluoroboron dipyrromethene and picric acid.UV-Vis absorption and fluorescence emission data for the BODIPY derivatives were examined,and fluorescence titration experiments were test to assess the utility of 8-(4-aminophenyl)-1,2,6,7-tetraphenylfluoroboron dipyrromethene as fluorescent probe for selectively detection of picric acid.