The Synthesis And Application In Molecular Recognition Of Fluorescent Probes Based On Chiral BINOL-Sugar

In recent years,fluorescent probes have been widely used in molecular and ion recognition due to their high sensitivity,good selectivity,short response time and convenient operation.Among them,BINOL has been widely used in the synthesis of fluorescent chemical sensors with high molecular and ion selectivity due to its unique C₂-axis chirality,rigidity,stable chemical properties,good fluorescence properties and wide sources.Fluorescent probes based on BINOL derivatives have been widely used for molecular recognition in recent years,especially for selective recognition of chiral small molecule,such as D-/L-amino acids.Therefore,a series of novel chiral BINOL-based fluorescent probes W1-W12 were designed and synthesized by introducing unique glycosyl-based structures such as glucose,ribose and xylitosyl,and their applications in optical properties and molecular recognition were investigated in order to realize the recognition of chiral small molecules with high sensitivity and selectivity.This thesis comprises several sections as following:In Chapter 1,the structure,recognition mechanism and application of chiral chemical fluorescent probes were introduced,and the research status of chiral binaphthol and its derivatives on fluorescent probes in recent years was summarized.In Chapter 2,four BINOL-glucose chiral fluorescence probes W1-W4 were designed and synthesized.It was found that W1 and W2 could selectively recognize sinconine/sinconidine in methanol system.At the same time,W1 could recognize the lazole drug molecules.For W3 and W4,omeprazole molecules could be selectively identified.Both[W3-20 eq Fe³⁺]and[W4-20 eq Fe³⁺]could perform specific selective recognition of Cys.Meanwhile,the lowest detection limits of[W3-20 eq Fe³⁺]and[W4-20 eq Fe³⁺]for Cys were 1.93×10^-7M and 4.00×10^-7M,respectively,and both of them were 1+1 complexed with Cys.In Chapter 3,four BINOL-ribose chiral fluorescence probes W5-W8 were designed and synthesized.The results showed that W5 and W6 could be selective recognition of cinconine/cinconidine in methanol system.While W5 could selectively recognize omeprazole molecules,W6 could not recognize a single drug molecule.For W7 and W8,W8 could selectively identify Fe³⁺,and its detection limit was 4.67×10^-8M.The complex of W8 and 10.0 eq Fe³⁺could be selectively identified for Cys,and the detection limit was 4.52×10^-7M.Similarly,in the presence of 10 eq Fe³⁺,W7probe could also be selectively identified for Cys,and the detection limit for Cys was6.22×10^-8M.In Chapter 4,four BINOL-xylose chiral fluorescence chemical sensors W9-W12were synthesized.The study showed that W9 and W10 could selectively identify sinconine/sinconidine in methanol system.W10 could selectively identify omeprazole drug molecules,and W9 could not identify omeprazole drug molecules.For W11,the probe could not selectively identify drug molecules such as omeprazole.[W11-10eq Fe³⁺]could be used for specific selective identification of Cys,and its anti-jamming ability was found to be good through anti-jamming experiments.The lowest detection limit of[W11-10 eq Fe³⁺]for Cys was LOD=6.34×10^-8M.Therefore,the research of this paper provides a direction for the preparation of fluorescent probes that can identify and detect the molecules of pazolium drugs,which has certain reference significance.In addition,this study provides ideas for the future design and synthesis of fluorescent probes for the detection of Cys with specific selective recognition.At the same time,it has certain practicality in detecting the Cys content in beverages,food and animal feed.