Preparation And Application Of Heterocyclic Derivative Molecular Fluorescent Probe

Supramolecular chemistry has a wide range of contents,among which molecular recognition is cores of supramolecular chemistry research.Molecular recognition is mainly about the recognition of anion,neutral molecule and macromolecule.Among them,the identification of anion and cation is the most basic and needs urgently to develop and enrich.The dual-channel probe with simple structure,good water solubility and strong anti-interference ability is a popular research field of ion recognition.Based on this,we designed and synthesized three kinds of Heterocyclic derivative molecule fluorescent probes,and studied their ionic properties via spectroscopic techniques and theoretical calculations et al.The thesis mainly consists of four parts:Chapter one:Mainly introduces the basic concepts of supramolecular and supramolecular chemistry,the ion recognition mechanism and the significance of ion recognition.The research progress of ion recognition of Heterocyclic derivative molecule is reviewed,mainly summarizes the four types of heterocyclic aromatic derivative fluorescence probe?1?The nitrogen heterocyclic aromatic derivative fluorescence probe?2?the oxygen-containing heterocyclic aromatic derivative fluorescence probe;?3?fluorescent probe containing sulfur Heterocyclic derivative molecule;?4?heterocyclic aromatic hydrocarbon derivative fluorescent probe containing a variety of heterocyclic atoms.Chapter two:We designed and synthesized chemosensor F1 based on4-methyl-7-hydroxy-8-aldehyde coumarin,which has an"turn-on"fluorescence response to cyanide in DMSO/H₂O?5:5,v/v;pH=7.20?solution.The electron-absorbing group?hydroxyl group?of the sensor F1 prevents intramolecular charge transfer?ICT?between the benzene ring and the coumarin group.However,the protons on acylhydrazone and hydroxyl group are removed by deprotonation with the addition of CN-,which enables ICT between the phenyl and coumarin groups.This recognition mechanism was confirmed by 1H-NMR titration and quantum chemical calculation?DFT?.In addition,the fluorescence detection limit is relatively low?9.92×10^-88 M?.It is worth mentioning that not only the sensor F1 has been successfully used to detect cyanide anions in food samples,but also a test strips based on F1 was prepared,which can easily and quickly detect CN-in water samples.Chapter three:Adual-channel chemosensor based on benzimidazoled for detection of Cu²⁺was designed and synthesized.The detectionprocess of Cu²⁺has good anti-interference toward other common cations.Fluorescence detection limit is 9.09×10-9 M.Interaction mechanism between F2 and Cu2+was ligand-metal charge transfer?LMCT?that was confirmed via experimental and theoretical calculations.In addition,the fluorescence change of F2 after the addition of Cu²⁺and EDTA was used as an ultra-sensitive IMPLICATION logic gate at the molecular level.At the same time,the molecular keyboard experiment has realized the information protection at the molecular level.More importantly,the test strips based on F2 can be easily and quickly applied to the detection of Cu²⁺in practical application.Chapter four:We designed and synthesized a carboxylic acid-functionalized coumarin derivative sensor F3,which has a dual-channel response to CN^-in DMSO/H₂O?2:3,v/v;pH=7.20?solution with a fluorescence detection limit of 3.09×10-8 M.Since the fluorescence returned to the initial state after AcOH was added to the F3-CN^-system,so F3 is a reversible fluorescence chemosensor.Based on this,we applied it to the ultrasensitive IMPLICATION logic gate.In addition,we made a test strips that can be used to quickly and conveniently detect CN-.According to various characteristics and applications of sensor F3,it can be concluded that sensor F3 is a promising CN^-detection methods with strong anti-interference ability,easy to use,fast response speed and low detection limit.