Synthesis And Study Of BODIPY-acetophenone Fluorescent Dyes

In the past twenty years,organic fluorescent dyes have been characterized by a broad range of applications in molecular probes,OLEDs,bio-imaging process and analysis.Due to its excellent optoelectronic properties and controllable structure,most chemists and biologists were attracted by it and devoted themselves to its investigation.Typical family members of organic fluorescent dyes include fluorine-boron complexes,rhodamine,coumarins,and naphthalimide etc.BODIPY is the typical members of fluorine-boron complexes and draw scientist's attention by high molar extinction coefficient,quantum yield,insensitive to polarity environment,excellent thermal/optical stability,and large Stoke's shift.By Vilsmerier-Haack and aldol condensation,a series of BODIPY derivatives with different electron-donating and withdrawing group attached.Corresponding investigation about their optophyscial properties configured the following dissertation.In chapter one,basic principles and theories about the generation of fluorescence were introduced with typical fluorescent dyes as examples.The development of BODIPY derivatives reviewed and a proposal of this dissertation was put forward based on the research directions.In chapter two,a molecular probes based on BODPY was synthesized and fully characterized.And the recognition site was activated by intramolecular hydrogen bonds,which could produce fast fluorescent response with the existence of thiol amino acids.The probe was configured by BODIPY(signal group),?,?-unsaturated carbonyl group(responsive group),and hydroxyl(active group).Based on its response to the thiol amino acids in cells,a distinct cell image could be obtained.Its detailed absorption and emission were also investigated in various solvent and poly(methyl methacrylate)(PMMA).In chapter three,an aldehyde was introduced to BODIPY with high yield.And a series of BODIPY derivatives was synthesized by condensation between aldehyde and aromatic ketone.Detailed absorption and emission behaviors were investigated in various polarity organic solvent and in PMMA.This series of BODIPY derivatives significant shift their emission maximum by comparison to the parent BODIPY.However,the electron-donating and withdrawing group attaching to the molecular structure doses not led to obvious emission change furtherly.Only individual,such as chloroform,could lead to interesting emissionbehavior.In chapter four,other fluorescent units with acetyl attached were condensed with BODIPY-CHO and configured fluorescent dyes with multifluorophore.Correspondingly,their absorption and emission behaviors were also investigated in various polarity organic solvent and in PMMA.Energy transfer could be significant influenced by polarity environment.In chapter five,conclusion and perspective were given based on current development and our investigation.