Studies On Synthesis And Properties Of Benzoyl Hydrazone Derivatives-Based Diarylethene Probes

Among the various photochromic materials,diarylethene compounds have been extensively researched since their appearance due to their excellent photochromic properties,outstanding thermal stability and fatigue resistance,as well as their potential applications in information storage,molecular switches,and pigments.By modifying aromatic heterocycles of diarylethene units with specific fluorescent groups,we can obtain a number of unique diarylethene moleculars having detection functions,which not only have photoresponses,but also ionic responses,acid-base responses,or amino acid responses,etc.However,most of these diarylethene moleculars reported have demonstrated specificity detection.In this dissertation,based on the review of the research progress of diarylethene compounds,a series of diarylethene moleculars with multiple recognition effects of anions and cations were obtained by decorated with benzoyl hydrazone derivatives.The main research contents are as follows:In chapter one,the detection mechanism of fluorescent probes and the research progress of diarylethene probes have been summarized.Based on these facts,the research content of this paper was proposed.In chapter two,the diarylethene probe DTC modified by benzoyl hydrazone,chromone groups was designed and synthesized.UV spectra studies showed that DTC had good photochromic properties and thermal stability.Besides,DTC had a specific colorimetric detection effect toward CN^-.Fluorescence spectra researches showed that the fluorescence relay-detection effect of DTC toward Al³⁺and Cr³⁺.The interactions between DTC and CN^-,Al³⁺,and Cr³⁺were further investigated by¹H NMR and mass spectrometry.In chapter three,the diarylethene probe DTP modified by benzoyl hydrazone and pyridine groups was designed and synthesized.UV spectra studies showed that DTP exhibited good photochromism.Through fluorescence spectra studies,it was found that DTP had high selectivity and high sensitivity in detecting Zn²⁺.The addition of Zn²⁺resulted in a 154-fold increase in fluorescence intensity.The interaction between DTP and Zn²⁺was researched by means of¹H NMR and mass spectrometry.In addition,further investigations of fluorescence spectra revealed that the chelate DTP-Zn²⁺had high sensitivity for the detection of HSO₄^-and H₂PO₄^-.In chapter four,the diarylethene probe DTPQ modified by benzoyl hydrazone,pyrrole and quinoline groups was designed and synthesized.UV spectra studies showed that DTPQ had good photochromic properties.Fluorescence spectra researches found that DTPQ had high selectivity for the recognition of Zn²⁺.In addition,further investigations on fluorescence spectra exhibited that the complex DTPQ-Zn²⁺can detect the presence of phosphates,including PO₄^3-,HPO₄^2-,and H₂PO₄^-.Phosphates will induce the fluorescence quenching behavior of DTPQ-Zn²⁺.In chapter five,the diarylethene probe DTSQ modified by benzoyl hydrazone,benzothiophene and quinoline groups was designed and synthesized.UV spectra studies showed that DTSQ had good photochromic properties and fatigue resistance.Fluorescence spectra studies demonstrated that DTSQ had highly selective detection effect toward Zn²⁺.The interaction among DTSQ and Zn²⁺was studied by Job’s plot titration experiments,¹H NMR and mass spectrometry.In addition,the complex DTSQ-Zn²⁺can further detect HSO₄^-and H₂PO₄^-with fluorescence quenching phenomenon.