The Design,Synthesis And Fluorescence Properties Of BINOL-based Boron Compounds

Using the cheap and easily available 1,1’-binaphthol as the basic framework,we design and synthesis a series of boron compounds and study their sensing properties for thiol-containing amino acids as fluorescent probes.The main content includes three chapters:The first chapter introduces the general structure of fluorescent probes and several recognition mechanisms of fluorescent probes(including PET,ICT,ESIPT,etc.).At the same time,it summarizes the development of BINOL derivatives in recent years.Emphasis was placed on the chiral recognition using BINOL derivative as fluorescent probes,and the interaction between probes and chiral substances.In the second chapter,we design and synthesize some BINOL-based boron compounds using1,1’-binaphthol as the starting material which is easy to obtain and has low fluorescence.The boron compounds have strong fluorescence,and their fluorescent colors range from green,blue to yellow.After the coordination with boron atom,the substituent group of BINOL will be fixed to expand the conjugated system.Thecompounds will lay a certain foundation for the construction of a new BINOL-based fluorescent probes,and also will be used to prepare full-wavelength luminescent materials.In the third chapter,a fluorescent probe(R)-a with acryloyl group was designed and synthesized based on the above boron compounds.After studying of the fluorescence properties of(R)-a,the results of chiral recognition for cys were obtained in spectrally pure DMF solvent.The mechanism of recognition was as follow: The first step is that the 1,4-conjugate addition occurred between the thiol group of Cys and the acryloyl group of(R)-a.The second step is that the amino group of Cys attacked the carbonyl group of the probe resulting a seven-membered ring compound,which than falls off to obtain the starting boron compound.Due to the different configurations,the reaction rates of L-Cys and D-Cys show different results.Even in the same concentration of L-Cys and D-Cys,the fluorescence responses of the probe also show different results.