Synthesis And Properties Of BODIPY-indenone Fluorescent Dyes And Naphthalimide Fluorescent Dyes

Recently,a new type of organic fluorescent dye based on BODIPY was emerged and various derivatives were configured and excellent opt-physical properties were developed.Gradually,researchers' intensive attention was captured.BODIPY dyes have several optimal characteristics,including large molar absorptivities,high quantum yields of emission,reasonably sized Stokes shifts,and insensitive to polarity/pH.Such potential attracted the interest of material and biotechnological scientists and configured an amazing perspective.In chapter 1,two parts are involved.The first part mainly concerns the development of BODIPY dyes and its benefit to the environment and various biosystems.Especially,BODIPY dyes have been systemic engineered and applications in our daily life.Another part mainly concerns unique character of the coumarin derivatives and their usage in functional materials and dyes.Based on the review of the two parts,ideas of this dissertation was configured and presented.In chapter 2,the synthesis of the target compounds was introduced.It was synthesized with3,4,5-trihydroxybenzoic acid methyl ester as the starting materials,via hydrolysis to yield the acid,then treated with thienyl chloride to give the acid chloride.Subsequently,the acid chloride was condensed with2,4-dimethylpyrrole,yielding BODIPY framework.An aldehyde could be introduced in high yield by Vilsmeier-Haack reaction at the ?-position.Finally,3-dicyanovinyl-1-ethanone was condensed with the introduced aldehyde and configured a seven membered ring,attaching to the framework of BODIPY.The absorption and emission properties of condensed product were measured in different polarity solvent.A detailed discussion was given in the text,including its unique response toward F-.In chapter 3,a series of fluorescent dyes was designed and synthesized by 1,8-naphthalimide and coumarin.Detailed absorption and emission properties in various organic solvents were provided.In addition,unique response toward F-(in dioxane),Fe3+(in dichloromethane),and oxidant(in dioxane)were also investigated in detail.In chatper 4,a conclusion and perspective were presented.