The Design,Syntheses And Fluorescent Sensing Properties Of Boron Compounds Based On 1,1′–Binaphthyl Derivatives

Molecular recognition as one of the themes of supramolecular chemistry,has been widely applied in many fields such as life sciences,food safety,environmental monitoring,information delivery and so on.Among the current methods,fluorescence detection has become the most common approach in the field of molecular recognition due to its simple operation,low cost,high selectivity,high sensitivity and rapid detection,etc.This dissertation focused on design and syntheses of boron compounds based on1,1′–binphthol（BINOL）skeleton,as well as detection and recognition of mercapto-amino acids using them as fluorescent probes.The main works are as follows:In chapter one,we mainly introduced the structure of fluorescent probe,various fluorescent sensing mechanisms,and research progress of chiral recognition based on BINOL derivatives,emphasizing different action modes between fluorescent probes and chiral analytes.As shown in chapter two,a series of boron compounds with strong fluorescence based on BINOL scaffold have been synthesized using non-fluorescent BINOL-3-aldehyde as a starting material which is easily available.The fluorescent color contains yellow,green-yellow,green and blue.The pivotal roles of the B^III may be stabilization by coordination with appropriate substituents to form a extendedπsystem with a naphthalene ring in BINOL,thereby enhancing conjugation and charge transfer along the molecular axis.The result has laid a good foundation on preparation of full-band light-emitting materials and design of novel fluorescent sensors.In chapter three,starting from the above luminescent boron compounds,（R）-10 containing acryloyl was synthesized as a fluorescent probe which demonstrated selective and chiral recognition of Cys over Hcy and GSH in DMF solution for the first time.This is presumably due to the cyclization reaction and subsequent elimination of seven-membered ring fragment between Cys and the probe.Because of different steric hindrance caused by two configurations,reaction rates of L-Cys andr D-Cys to（R）-10 are distinct,eventually resulting in discriminating fluorescence response to these two enantiomers at the same concentration.