The Design,Synthesis And Properties Of Fluorescent Probes Of Coumarin Derivertives Based On BINOL Skeleton

Over the past decades,due to the special structure and properties of supramolecular system,more and more scientists around the world focused on the system.As a result,the supramolecular system was used in the fields of molecular self-assembly,molecular devices,nano-organic materials.And the influence in the fields of material science and life science also was very important.with the development of supramolecular chemistry,molecular recognition has developed rapidly in many fields including bio-imaging,molecular biology,environmental monitoring,and so on.Due to its excellent selectivity,high sensitivity,simple operation,large spectral changes before and after the reaction,the chemodosimeter attracted much attention.In this paper,BINOL was used as the skeleton of fluorophore,combined with coumarin structure,a series of fluorescent probes of coumarin derivatives were designed and synthesized,and the properties were studied in detail.The main work of this paper includes the design and synthesis of chemodosimeters based on the irreversible chemical reactionto sensing Cys.The full text is divided into three chapters:In the first chapter,the research background related to this thesis is mainly elaborated.The fluorescence recognition mechanism of chemodosimeters(including PET,FRET,etc.)and the development of amino acid detection in recent years were introduced.In the second chapter,a cheap and weak fluorescence material—BINOL was used as skeleton of probe to design and synthesis of a series coumarin chemodosimeters L~1-L~6,the characterization of the structure of which were carried on.In chapter 3,the fluorescence properties of the chemodosimeters L~1-L~6 were studied.It was found that L~1-L~4 could selectively detect Cys.The reaction between chemodosimeters and Cys could complete within 30 min,and the fluorescence quenching was occurred while excited by 340nm.All the experimental results showed that L~1-L~4 can identify the Cys specifically even in the presence of other amino acids.This is because the 1,4-conjugate addition generated between the chemodosimeters and Cys,and subsequent elimination of seven-membered ring fragment was occurred.