CN107417681A - One kind contains cumarin thiadiazolyl group schiff bases fluorescent probe compounds and its production and use - Google Patents

One kind contains cumarin thiadiazolyl group schiff bases fluorescent probe compounds and its production and use Download PDF

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CN107417681A
CN107417681A CN201710450445.3A CN201710450445A CN107417681A CN 107417681 A CN107417681 A CN 107417681A CN 201710450445 A CN201710450445 A CN 201710450445A CN 107417681 A CN107417681 A CN 107417681A
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fluorescent probe
probe compounds
cumarin
thiadiazolyl group
schiff bases
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CN107417681B (en
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朱维菊
方敏
李村
吴振玉
韦蔚
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Anhui University
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Anhui University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

The invention discloses one kind containing cumarin thiadiazolyl group schiff bases fluorescent probe compounds and its production and use, wherein the structural formula containing cumarin thiadiazolyl group schiff bases fluorescent probe compounds is：Fluorescent probe compounds of the present invention have multifunctionality, can be realized by ultraviolet-visible spectrophotometry and fluorescent spectrometry to Cu2+And Hg2+The identification of ion and quantitative detection, there is good anti-interference, high selectivity and sensitivity in the presence of other ions.

Description

One kind contains cumarin-thiadiazolyl group schiff bases fluorescent probe compounds and its preparation Method and purposes
Technical field
The present invention relates to one kind containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds and preparation method thereof and to use On the way, metal ion detection and fluorescent molecular probe field are belonged to.
Background technology
Heavy metal ion pollution turned into the world one it is very serious and urgent the problem of, this is due to have A little heavy metal ion to environment and human body even if also producing potential hazard at very low concentrations.In recent years, with chemistry Sensor develops rapidly, and fluorescence probe research is more and more by people in numerous areas such as chemistry, biology, medical science and environment Concern, turn into a current big study hotspot.Fluorescent probe technique because with the good, high sensitivity of selectivity, it is simple and quick and The detection of each metal ion species need not be widely used in by the advantages of expensive instrument.Utilize ultraviolet/fluorescence property Ion can quantitatively or qualitatively be analyzed with the relation of ion concentration, it is convenient, fast, there is higher selectivity and spirit Sensitivity, it is very suitable for the real-time or in situ detection of heavy metal ion.
Copper is micro- and required nutrient important in life system.Copper electrodissolution very little, but copper lacks and can caused Growth and the disorder of metabolism.The change that copper balances in cell can cause suppress neurogenic disease, as Menkes syndromes, Wilson diseases, Familial Occurrence posterior spinal sclerosis, Alzheimers disease and Prion diseases etc..The copper of weight just because of to(for) life Will, distribution of the copper in cell is by strict control.Copper has variable valence, and electron transmission, oxidation are participated in life entity A series of processes such as reduction, directly research and simulation cuprein and cuprase are always the focus of scientist's research.Therefore, establish A kind of easy, sensitive method detection copper ion is necessary.
Mercury is a kind of important heavy metal element, is widely present in nature, is most threatening to human body and nature One of heavy metal element, therefore a kind of method for fast and accurately detecting mercury ion is found, for environmental pollution, detection food peace Congruence has important theoretical and practical values.At present to Hg2+The research of assay method is much reported, but there is also instrument Expensive, the shortcomings of analysis cost is high.Fluorescence detection has the advantages that high sensitivity, selectivity single-minded and response time are short, closely In the past few years enjoy the favor of people.
In recent years, fluorescence probe research and application have been achieved for very big progress.Fluorescence probe be using probe with The change of photoluminescent property is realized to the recognition detection of target substance before and after target substance combines, have good selectivity, high sensitivity, The advantage such as real-time in-situ detection and operating method simplicity.
The content of the invention
The present invention is intended to provide a kind of contain cumarin-thiadiazolyl group schiff bases fluorescent probe compounds and preparation method thereof And purposes.Because the recognition performance of fluorescence probe and the space structure of probe molecule are relevant, so the present invention is based on C=N isomeries Change mechanism, using cumarin aldehyde as fluorescent chromophore parent, design and synthesize the Schiff base derivatives with C=N structures, simultaneously Containing coordination atoms such as O, S and N in molecule, ligand molecule can be formed with some metal ions, produce specific ultraviolet, fluorescence Phenomenon.
The present invention contains cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, and its structural formula sees below formula 1：
Preparation method of the invention containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, is by based on tonka-bean The product that the aldehyde of element obtains with the progress condensation reaction of 5- amido -1,3,4- thiadiazoles -2- mercaptan.
The aldehyde based on cumarin is 3- aldehyde radical -7-N, TMSDEA N diethylamine butylcoumariii.
Preparation method of the invention containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, comprises the following steps：
Weigh 3- aldehyde radical -7-N, TMSDEA N diethylamine butylcoumariii 1.0mmol and 5- amido -1,3,4- thiadiazoles -2- mercaptan 1.1mmol is simultaneously dissolved in 10mL absolute ethyl alcohols respectively, is mixed in after stirring and dissolving in reactor, and adds a drop glacial acetic acid and urge Agent, it is warming up to 75 DEG C of back flow reaction 6h；Reaction cools down after terminating, and filters, and absolute ethyl alcohol recrystallization, filters, washs and dry, Obtain target product.
The synthetic route of target product of the present invention is as follows：
Purposes of the invention containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, is qualitatively or quantitatively to examine Survey Cu2+Shi Zuowei detection reagent applications.
Application of the invention containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, is entered in water-bearing media Row uv-visible absorption spectra determines, and is realized by the change of solution colour to Cu2+Qualitative detection.
The water-bearing media is acetonitrile and water by volume 1：1 mixed solution formed.
Application of the invention containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, is entered in water-bearing media Row uv-visible absorption spectra determines, and realizes to Cu2+Quantitative detection.
The water-bearing media is acetonitrile and water by volume 1：1 mixed solution formed.
Purposes of the invention containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, is qualitatively or quantitatively to examine Survey Hg2+Shi Zuowei detection reagent applications.
Application of the invention containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, is entered in water-bearing media Row fluorescence spectrometry, realized by the change of fluorescence intensity to Hg2+Qualitative or quantitative detection.
The water-bearing media is acetonitrile and water by volume 1：1 mixed solution formed.
Target product of the present invention has C=N structures, the thiadiazoles Schiff base derivatives containing substituted cumarin group, its Molecular characterization is to contain hydrophilic mercapto groups in schiff base compounds structure, while contains the coordination such as O, S and N in molecule Atom, ligand molecule can be combined to form with some metal ions in water-bearing media, produce specific ultraviolet, fluorescence phenomenon.
Fluorescent probe compounds of the present invention can be used for Cu2+Identification, the detection of ion, there is stronger resist to various metals ion Interference performance, and fluorescent probe compounds of the present invention and Cu2+Ar ion mixing produces obvious color change phenomenon and can realized Bore hole identifies and colorimetric analysis；Fluorescent probe compounds of the present invention can also identify Hg2+Ion.
Beneficial effects of the present invention are embodied in：
Fluorescent probe compounds of the present invention have multifunctionality, can pass through UV-VIS spectrophotometry and fluorescence light Spectrometry is realized to Cu respectively2+And Hg2+The identification of ion.Utilize UV-VIS spectrophotometry Selective recognition Cu2+Ion, profit It can be selected to identify Hg with fluorescent spectrometry2+Ion.Fluorescent probe compounds of the present invention can be used in aqueous medium to Cu2 +Or Hg2+The quick identification of ion, quantitative detection, and to Cu2+Or Hg2+Ion identification is with higher selectivity and preferably Antijamming capability, and obvious color change phenomenon can realize bore hole identification and colorimetric analysis.
Brief description of the drawings
Fig. 1 is that fluorescent probe compounds L of the present invention in acetonitrile and water volume ratio is 1：Different gold are added in 1 mixed solution Belong to the ultra-violet absorption spectrum of ion, illustration is addition Cu2+L color change.
Fig. 2 is addition Cu2+The fluorescent probe compounds L of ion is 1 in acetonitrile and water volume ratio：1 mixed solution is ultraviolet- Visible absorption spectra spectra for titration figure.
Fig. 3 is that fluorescent probe compounds L in acetonitrile and water volume ratio is 1：Metalloform-selective in 1 mixed solution With anti-interference block diagram；L is represented in acetonitrile and water volume ratio as 1：Different metal ions are added in 1 mixed solution UV absorption intensity；Represent in L acetonitriles and water volume ratio as 1：Different metal ions and Cu are added in 1 mixed solution2 +UV absorption intensity (the λ of ionmax=506nm).
Fig. 4 is that fluorescent probe compounds L in acetonitrile and water volume ratio is 1：Different metal ions are added in 1 mixed solution Fluorescence spectrum (λex=500nm).
It is that fluorescent probe compounds L in acetonitrile and water volume ratio is 1 in Fig. 5：Hg in 1 mixed solution2+Fluorescence titration Spectrum (λex=500nm).
Fig. 6 is that fluorescent probe compounds L in acetonitrile and water volume ratio is 1：In 1 mixed solution metalloform-selective and Anti-interference block diagram；Represent the fluorescence intensity that different metal ions are added in L acetonitrile solutions；Represent in acetonitrile It is 1 with water volume ratio：Different metal ions and Hg are added in 1 mixed solution2+Fluorescence intensity (the λ of ionem=568nm).
Embodiment
The present invention can be further illustrated by the following examples, but be not limited solely to embodiment.
Embodiment 1：The synthesis of fluorescent probe compounds (L) of the present invention
Weigh 0.245g (1.0mmol) 3- aldehyde radical -7-N, TMSDEA N diethylamine butylcoumariii and 0.147g (1.1mmol) 5- amine Base -1,3,4- thiadiazoles -2- mercaptan are simultaneously dissolved in 10mL absolute ethyl alcohols respectively, and stirring makes it fully dissolve；Person is mixed and added In round-bottomed flask, and add a drop glacial acetic acid and make catalyst, be warming up to 75 DEG C of backflow 6h, after reaction solution cooling, filter, anhydrous second Alcohol recrystallizes, and filters, washs and dries, obtains product 0.297g, yield 82.4%.
FT-IR (KBr, cm-1)：3431 (S-H stretching vibrations), 2976,2929 (- CH2With-CH3Stretching vibration), 1738 (C =O stretching vibrations), 1615,1502 (phenyl ring stretching vibrations), 1348 (- C-H flexural vibrations), 1132 (- C-N stretching vibrations), 683 (- N-H out-of-plane bending vibrations).
1H NMR(400MHz,DMSO-d6):1H NMR(400MHz,DMSO):δ(ppm)14.42(s,1H,-SH),8.68 (s, 1H ,-CH=N-), 8.59 (s, 1H ,-CH=), 7.68 (d, 1H ,-CH=), 6.82 (dd, 1H ,-CH=), 6.61 (d, 1H ,-CH=), 3.50 (q, 4H ,-CH2-),1.15(t,6H,-CH3).ESI-MS:m/z 361.08for C16H16N4O2S2.
Embodiment 2：Fluorescent probe compounds L uv-visible absorption spectra measure
Precise fluorescent probe compounds L mass 3.6mg, dissolve and be configured to concentration as 1.0 × 10-2Mol/L second Nitrile stock solution；It is 1 with acetonitrile and water volume ratio：Storing solution is diluted to concentration as 1.0 × 10 by 1 mixed solution-5Mol/L's Solution to be measured.It is 1.0 × 10 to take 3mL concentration-5(thickness of quartz colorimetric utensil is mol/L solution to be measured in quartz colorimetric utensil 1cm), 3 μ L concentration are then respectively adding as 1.0 × 10-2Mol/L each metal ion species (Na+, K+, Ag+, Ca2+, Mg2+, Mn2+, Cd2+, Cr3+, Cu2+, Ni2+, Co2+, Fe3+, Fe2+, Hg2+) the aqueous solution, shake up, after 1 minute determine solution ultraviolet-visible inhale Receive spectrum (see Fig. 1).Before adding metal ion, fluorescent probe compounds L uv-visible absorption spectra, which is shown in 506nm, to be had One clear and definite absworption peak, as addition Cu2+After ion, absworption peaks of the fluorescent probe compounds L at 506nm weakens, Occurs a new absworption peak at 446nm, its solution colour is also changed into yellow green (such as the illustration institute in accompanying drawing Fig. 1 from yellowish-brown Show), it can visually observe, there is " bore hole identification " function, fluorescent probe compounds L can be used as ultraviolet identification and bore hole to know Other Cu2+The colorimetric probe of ion；And under the same conditions, other metal ions are such as：Na+, K+, Ag+, Ca2+, Mg2+, Mn2+, Cd2 +, Cr3+, Zn2+, Ni2+, Co2+, Fe2+, Hg2+The addition uv-visible absorption spectra big to L have no significant effect, solution face Color base does not originally change.
Embodiment 3：Fluorescent probe compounds L uv-visible absorption spectra titration experiments and the measure of test limit
It is 1.0 × 10 to take 3mL concentration-5Mol/L solution to be measured in quartz colorimetric utensil, be separately added into 3,6,9,12,15, 18th, 21,24,27,30 μ L concentration are 1.0 × 10-3Mol/L Cu2+Deionized water solution, shake up, the purple of solution is determined after balance Outside-visible absorption spectra (as shown in Figure 2).With Cu2+The addition of ion, absorbances of the fluorescent probe compounds L at 446nm Gradually enhancing, and the trap at 506nm gradually weakens, and occurs an obvious isocenter at 469nm, illustrates in acetonitrile It is 1 with water volume ratio：Fluorescent probe compounds L energy and Cu in 1 mixed solution2+Ion forms stable complex, Cu2+From Son is 1.0 × 10-6~1.2 × 10-5In the range of mol/L, Cu2+Ion concentration is in preferable line with absorbance change amount at 446nm Sexual intercourse (R=0.98), by the way that fluorescent probe compounds L is calculated to Cu2+The detection of ion is limited to 1.28 × 10-6mol/ L。
Embodiment 4：Fluorescent probe compounds L is to Cu2+The selectivity and anti-interference of ion identification
It is 1.0 × 10 to take 3mL concentration-5Mol/L solution to be measured in quartz colorimetric utensil, add 3 μ L concentration be 1.0 × 10-2Mol/L Cu2+After ion, then 3 μ L concentration are separately added into as 1.0 × 10-2Mol/L each metal ion species (Na+, K+Deng) Solution, shake up, its ultra-violet absorption spectrum (as shown in Figure 3) is determined after 1 minute, as a result show and add other metal ions such as：Na+, K+Deng being had little to no effect to fluorescent probe compounds L uv absorption property, this has indicated that fluorescent probe compounds L To Cu2+Ion identification has higher selectivity and preferable antijamming capability.
Embodiment 5：Fluorescent probe compounds L fluorescence spectrometry
It is 1.0 × 10 to take 3mL concentration-5Mol/L solution to be measured is then respectively adding 3 μ L concentration in quartz colorimetric utensil For 1.0 × 10-2Mol/L each metal ion species (Na+, K+, Ag+, Ca2+, Mg2+, Mn2+, Cd2+, Cr3+, Cu2+, Ni2+, Co2+, Fe3+, Hg2+) solution, shake up, its fluorescence emission spectrum is determined (such as Fig. 4 institutes under λ=500nm excitation wavelength after 1 minute Show), when being as a result displayed without adding metal ion, fluorescent probe compounds L has a weaker fluorescence peak at λ=568nm, Hg2+To fluorescent probe compounds L, the fluorescence radiation peak at 568nm has obvious enhancement effect of fluorescence for the addition of ion.Add Hg2 +Afterwards, fluorescent probe compounds L fluorescence peak intensity adds about 5 times；And other metal ions are such as：Na+, K+, Ag+, Ca2+Deng Without obvious Enhancement of Fluorescence.
Embodiment 6：Fluorescent probe compounds L fluorescence spectroscopic titration experiment and the measure of test limit
It is 1.0 × 10 to take 3mL concentration-5Mol/L solution to be measured in quartz colorimetric utensil, be separately added into 3,6,9,12,15, 18th, 21,24,27,30,33,36,39,42,45,48 μ L concentration are 1.0 × 10-3Mol/L Hg2+Deionized water solution, shake up, put down The fluorescence spectrum (as shown in figure 5 of the drawings) of solution is determined after weighing apparatus, with Hg2+The addition of ion, fluorescent probe compounds L is in λex Fluorescence intensity under=500nm is excited gradually increases.By the relation curve of ion concentration and fluorescence intensity, 0.5 × 10-6~1.4 × 10-5In the range of mol/L, Hg2+Ion concentration and fluorescence intensity are in preferable linear relationship (R=0.99), fluorescence Probe compound L is to Hg2+The detection of ion is limited to 2.96 × 10-7mol/L。
Embodiment 7：Fluorescent probe compounds L is to Hg2+The selectivity and anti-interference of ion identification
It is 1.0 × 10 to take 3mL concentration-5Mol/L solution to be measured in quartz colorimetric utensil, add 3 μ L concentration be 1.0 × 10-2Mol/L Hg2+After ion, then 3 μ L concentration are separately added into as 1.0 × 10-2Mol/L each metal ion species (Na+, K+Deng) Solution, shake up, determine its fluorescence emission spectrum (as shown in accompanying drawing Fig. 6) after 1 minute under λ=500nm excitation wavelength, as a result Display adds other metal ions such as：Na+, K+Deng being had little to no effect to fluorescent probe compounds L fluorescence intensity, this is just Fluorescent probe compounds L is indicated to Hg2+Ion identification has higher selectivity and preferable antijamming capability.

Claims (8)

1. one kind contains cumarin-thiadiazolyl group schiff bases fluorescent probe compounds, it is characterised in that its structural formula is：
2. the preparation method containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds described in a kind of claim 1, its It is characterised by：
By the aldehyde based on cumarin and 5- amidos -1,3,4- thiadiazoles -2- mercaptan carries out condensation reaction, obtained target product.
3. preparation method according to claim 2, it is characterised in that：
The aldehyde based on cumarin is 3- aldehyde radical -7-N, TMSDEA N diethylamine butylcoumariii.
4. preparation method according to claim 2, it is characterised in that comprise the following steps：
Weigh 3- aldehyde radical -7-N, TMSDEA N diethylamine butylcoumariii 1.0mmol and 5- amido -1,3,4- thiadiazoles -2- mercaptan 1.1mmol And be dissolved in respectively in 10mL absolute ethyl alcohols, it is mixed in after stirring and dissolving in reactor, and add a drop glacial acetic acid and make catalyst, rise Temperature is to 75 DEG C of back flow reaction 6h；Reaction cools down after terminating, and filters, and absolute ethyl alcohol recrystallization, filters, washs and dry, obtain mesh Mark product.
5. the purposes containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds described in a kind of claim 1, its feature It is：It is in qualitatively or quantitatively detection Cu2+Or Hg2+Shi Zuowei detection reagent applications.
6. the application containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds described in a kind of claim 1, its feature It is：It is the progress uv-visible absorption spectra measure in water-bearing media, is realized by the change of solution colour to Cu2+Determine Property detection.
7. the application containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds described in a kind of claim 1, its feature It is：It is the progress uv-visible absorption spectra measure in water-bearing media, realizes to Cu2+Quantitative detection.
8. the application containing cumarin-thiadiazolyl group schiff bases fluorescent probe compounds described in a kind of claim 1, its feature It is：It is that fluorescence spectrometry is carried out in water-bearing media, is realized by the change of photoluminescence spectrum intensity to Hg2+It is qualitative or fixed Amount detection.
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CN110229147A (en) * 2019-06-21 2019-09-13 安徽大学 A kind of cumarin-benzothiazolyl hydrazone compounds and its preparation method and application
CN115073443A (en) * 2022-06-06 2022-09-20 辽宁师范大学 Visual fluorescence-enhanced copper ion fluorescence detection probe and preparation method thereof

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CN109239026A (en) * 2018-01-23 2019-01-18 齐齐哈尔大学 A kind of phosphinylidyne-containing amine group fluorescence probe is to Hg2+Fluorescence detection and application method
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CN108640867B (en) * 2018-06-13 2021-02-26 安徽大学 Fluorescent probe compound containing cyano-carbazolyl Schiff base as well as preparation method and application thereof
CN110229147A (en) * 2019-06-21 2019-09-13 安徽大学 A kind of cumarin-benzothiazolyl hydrazone compounds and its preparation method and application
CN115073443A (en) * 2022-06-06 2022-09-20 辽宁师范大学 Visual fluorescence-enhanced copper ion fluorescence detection probe and preparation method thereof
CN115073443B (en) * 2022-06-06 2023-07-07 辽宁师范大学 Visual fluorescence enhancement type copper ion fluorescence detection probe and preparation method thereof

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