Synthesis And Performance Of New Fluorescent Probes Based On Naphthalene Core

With the development of science and technology and the deepening of research,fluorescent dye molecules have been gradually applied to the fields of life science,biology and environmental detection.In the published reports,the absorption and emission wavelengths of most fluorescent dyes are in the ultraviolet or visible light region.Due to the autofluorescence and the ability to absorb fluorescence of biolo-gical tissues,most fluorescent dyes in the ultraviolet or visible light region have been used in the fields except biological detection.But the two-photon fluorescent probe has absorption peaks in the long-wave region,which can reduce damage and enhance the penetrating performance for biological imaging.This paper was based on fluorescent molecular chemistry.Resorcinol halide and M-hydroxythiophenol were introduced and reacted with anthocyanins to synthesize near-infrared fluorescent dye molecules M₁ and M₂ with a hemicyanine structure as the backbone.After detection,the maximum absorption wavelength of compound M₁in ethanol was 716 nm,and the fluorescence emission wavelength was 766 nm.We have designed and studied the recognition performance of compound M₁ on mercury ion(Hg²⁺)and copper ion(Cu²⁺).The test results showed that compound M₁ has a certain response to both mercury ion(Hg²⁺)and copper ion(Cu²⁺).We also designed and prepared the compound M₂,which greatly increased the penetrability of the fluorescent molecule due to the introduction of the heavy atom iodine.In addition,we also designed and synthesized two compounds of M₃ and M₄with 6-hydroxy-2-naphthaldehyde.Since 6-hydroxy-2-naphthaldehyde has both a hydroxyl group and an aldehyde group,these two groups can be modified separately or simultaneously.In this paper,The compounds M₃ and M₄ were synthesized with two recognition groups of 2,4-dinitrobenzenesulfonyl chloride and 2-（3-cyano-4,5,5-trimethylamine）Furan-2（5H）alkylene)malononitrile on the backbone of 6-hydroxy-2-naphthaldehyde.After detection,the maximum absorption wavelengths of compounds M₃ and M₄ were 350 nm and 468 nm,which were located in the ultraviolet and visible light regions,respectively.We studied the fluorescence performance of M₃ in different solvent ratios and the recognition performance of this fluorescent dye for substances such as m-hydroxythiophenol,sodium sulfide,sodium bisulfite,Cys,GSH and Hcy.In addition,the recognition performance is also studied in this paper of the substances containing sulfur such as m-hydroxybenzenethiol,sodium thiohydride,Cys,GSH and Hcy.The intermediates,by-products and target products synthesized in the design of this thesis were characterized by ¹H-NMR,¹³C-NMR,and MS to determine the structure of the compound.