Study On Synthesis And Recognition Properties Of Chiral Fluorescent Macromolecule Probe Based On Diacetylene Framework

So far,human beings have confirmed through a large number of scientific experiments that the origin of life conformation is all due to the asymmetry of matter.And people also found that chiral compounds often play a vital role in life systems.There-fore,the transformation of natural chiral compounds and the artificial synthesis of chiral compounds have gradually become a hot research field in recent years.Now we provides a new method to solve the predicament that existing chiral func-tional materials may encounter in current applications.In this paper,a series of monomers with chiral oxazoline derivative and achiral monomers containing fluorene functional groups were designed and copolymers were synthesized flexibly.The re-search in this paper is mainly summarized from the three parts,which greatly expands the types of chiral functional materials and possible application prospects,and further research its application in fluorescence sensing and asymmetric polymerization.(1)In the first chapter,a chiral derivative monomer 9,9-dipropionyl fluorene(1a)containing fluorene and a chiral monomer 2,containing chiral oxazoline were synthesized.2-dipropionate malononitrile derivative monomer((S)-2-(4-isopropyl-4,5-dihydrooxazole-2-yl)-2-(propyl-2-acetyl-1-yl)penta-4-nitrile)(1b)was used as chiral inducer.The polymerization of o-dichlorobenzene(O-DCB)was carried out by using Glaser coupling in oxygen atmosphere with cuprous chloride and N’-Tetramethylethylenediamine(TMED-Cu Cl)complex system as the catalytic system.The results show that the enantiomers of different amino acids can be recognized by changing the ratio of monomers in the polymer.(2)In the second part,we modified monomer 1a to provide more chiral recognition sites,and synthesized 9,9-dipropionatefluoren-2-formaldehyde(2a)and 9,9-dipropionate fluoren-2-methanol(2b)non-chiral monomers.A chiral compound(S)-2-(4-(tert-butyl)-4,5-dihydrooxazole-2-yl)-2-(prop-2-acetyl-1-yl)penta-4-nitrile(2c)was conjugated by Glaser to investigate the effect ofsteric hindrance on the helical confor-mation of copolymer.The recognition of chiral amino acids by different functional groups was studied.(3)In the third part,9,9-dipropionatefluoren-2-formaldehyde(2a)and(S)-2-(9H-fluoren-2-yl)-4-tert-butyl-4,5-dihydrooxazoline((S)-DTDH)(3a)were used as achiral and chiral monomer coupling polymerization respectively.A series of chiral helical polymers with different monomer ratios were synthesized as fluorescent probes.The structure and chiral properties of the polymer were characterized by1 HNMR,IR,CD and UV.The identification performance of eight chiral enantiomers by polymeric geophysical prospecting was investigated.It was found that there were obvious binding differences between tryptophan enantiomers and probes.