Research On The Synthesis And Properties Of Novel BODIPY Fluorescence Dyes

Dipyrromethene Boron Difluoride(BODIPY)and Aza-BODIPY fluorescent dyes were novel fluorescent compounds that have attracted extensive attention in recent 20 years.As near-infrared fluorescent dyes,they have good physical and chemical properties,such as: higher fluorescence quantum yields,longer fluorescence emission wavelength,narrow absorption and emission peaks,large molar absorption coefficients,relatively high thermal and photochemical stability and its chemicai structure can be easily tuned etc.At present,these dyes have been widely used in the fileds of ion probes,small molecule probes,fluorescence imaging,biomedical detection,and environmental science.In this dissertation,we reviewed the domestic and international research results on these novel fluorescent compounds.In addition,we had prospect for their future applications and development prospects.At the same time,we designed and synthesized a new type of BODIPY fluorescent dye with large Stokes shift,active substitution group and convenient biomarker.On this basis,we further developed a series of fluorescent dye intermediates with high yield,long wavelength,and even near infrared absorption.The main content of each chapter is described as follows:Chapter 1: prolegomenon,summarizing the mechanism of fluorescence generation,the influence conditions and factors of fluorescence,the types and characteristics of fluorescent dyes,described the prospects for the development of the most widely used fluorescent dyes BODIPY and Aza-BODIPY.In view of the above aspects,the paper planned the research purpose,significance and method of the research ideas,including molecular design and synthesis scheme.Chapter 2: the pyrrole derivatives were firstly synthesized via Knorr reaction.As an active group,aldehyde substituted pyridines and pyrazines were used for synthesizing a series of novel meso-substituted BODIPY fluorescent dyes.In this section,the aldehyde-modified substrates were reacted with two azole derivatives to give main skeleton of BODIPY,which were then condensed with other functional groups.Avoiding the complicated reaction of using BODIPY as raw materials and improving the reaction efficiency,the BODIPY dyes were obtained.At the same time,the structural characterization and optical properties of the synthesized BODIPY dyes have been demonstrated.The results show that the series of BODIPY fluorescent dyes have large Stokes shifts.For meso-substituted dye core,the absorption and the emission spectrum is almost constant in different polar solvents,which improves the accuracy of biological detection and extends its application range.Chapter 3: as the raw material,acetylpyridine was reacted with aromatic aldehydes to give a series of tetradentate azadipyrromethene(Aza-BODIPY dye intermediate)via intermolecular Michael addition reaction.The method conditions(solvent,acidity and alkalinity)and post-treatment are optimized.At the same time,the structural characterization and optical properties of the resulting tetradentate azadipyrromethene were measured.The results showed that the series of compounds have the near-infrared absorption phenomenon and implies the potential of synthesizing a new type of near-infrared fluorescent dye.Therefore,based on the predecessors,it's very hopeful to complete the final products by means of optimizing different conditions such as solvents,temperatures,and alkaline reagents.As for the final step of complexation of new Aza-BODIPY dyes containing pyridine groups,still further researchare under way.