CN114836201B - Zinc ion-mediated fluorescence sensor and preparation method and application thereof - Google Patents
Zinc ion-mediated fluorescence sensor and preparation method and application thereof Download PDFInfo
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- CN114836201B CN114836201B CN202210350357.7A CN202210350357A CN114836201B CN 114836201 B CN114836201 B CN 114836201B CN 202210350357 A CN202210350357 A CN 202210350357A CN 114836201 B CN114836201 B CN 114836201B
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- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 230000001404 mediated effect Effects 0.000 title claims abstract description 15
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000005562 Glyphosate Substances 0.000 claims abstract description 90
- 229940097068 glyphosate Drugs 0.000 claims abstract description 90
- 238000001514 detection method Methods 0.000 claims abstract description 40
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 31
- 239000000523 sample Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007995 HEPES buffer Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 150000003751 zinc Chemical class 0.000 claims abstract description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 241001122767 Theaceae Species 0.000 claims description 9
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004246 zinc acetate Substances 0.000 claims description 5
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 claims description 4
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 claims description 4
- OVZQVGZERAFSPI-UHFFFAOYSA-N quinoline-8-carbaldehyde Chemical group C1=CN=C2C(C=O)=CC=CC2=C1 OVZQVGZERAFSPI-UHFFFAOYSA-N 0.000 claims description 4
- MYUNWHTZYXUCIK-WEVVVXLNSA-N 2-[(E)-hydrazinylidenemethyl]phenol Chemical compound N\N=C\C1=CC=CC=C1O MYUNWHTZYXUCIK-WEVVVXLNSA-N 0.000 claims description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- 229960001763 zinc sulfate Drugs 0.000 claims description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims 1
- 239000000575 pesticide Substances 0.000 abstract description 8
- 230000007547 defect Effects 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 238000011534 incubation Methods 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 230000008859 change Effects 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 3
- 239000005947 Dimethoate Substances 0.000 description 3
- 239000005561 Glufosinate Substances 0.000 description 3
- 239000005949 Malathion Substances 0.000 description 3
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 3
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 3
- 229950001327 dichlorvos Drugs 0.000 description 3
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 3
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229960000453 malathion Drugs 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229960001952 metrifonate Drugs 0.000 description 3
- PZXOQEXFMJCDPG-UHFFFAOYSA-N omethoate Chemical compound CNC(=O)CSP(=O)(OC)OC PZXOQEXFMJCDPG-UHFFFAOYSA-N 0.000 description 3
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 3
- CNHYKKNIIGEXAY-UHFFFAOYSA-N thiolan-2-imine Chemical compound N=C1CCCS1 CNHYKKNIIGEXAY-UHFFFAOYSA-N 0.000 description 3
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- NXSVNPSWARVMAY-UHFFFAOYSA-N 1-benzothiophene-2-carbaldehyde Chemical compound C1=CC=C2SC(C=O)=CC2=C1 NXSVNPSWARVMAY-UHFFFAOYSA-N 0.000 description 1
- VZBLASFLFFMMCM-UHFFFAOYSA-N 6-methoxynaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(OC)=CC=C21 VZBLASFLFFMMCM-UHFFFAOYSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000840 electrochemical analysis Methods 0.000 description 1
- 238000000835 electrochemical detection Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004186 food analysis Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001795 light effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011897 real-time detection Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- G01N21/17—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
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
-
- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- 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
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
Abstract
A zinc ion-mediated fluorescence sensor and a preparation method and application thereof relate to the field of glyphosate detection, in particular to a preparation method of a zinc ion-mediated fluorescence sensor and application thereof in glyphosate detection. The preparation method of the fluorescence sensor comprises the following steps: and dissolving the fluorescent probe in an organic solvent/HEPES buffer solvent, adding inorganic zinc salt for incubation, and obtaining the fluorescent sensor. The fluorescent sensor can specifically identify the glyphosate, has strong detection specificity, high sensitivity and high speed, has small interference with other organophosphorus pesticides, and can realize qualitative and quantitative detection of the glyphosate. The method is used in the field of glyphosate detection, and can solve the defects of complex sample treatment, long time consumption, high cost and difficulty in large-scale conventional detection in the existing method for detecting glyphosate.
Description
Technical Field
The invention relates to the field of glyphosate detection, in particular to a preparation method of a zinc ion-mediated fluorescence sensor and application of the zinc ion-mediated fluorescence sensor in glyphosate detection.
Background
Glyphosate is a systemic, conductive, biocidal broad-spectrum organophosphorus herbicide developed by us Meng Shandou company in the 70 s of the 20 th century, and is widely used in farmland, orchards, forestry and other fields, and has become the most widely used herbicide in the world. However, in recent years, researches show that the glyphosate has certain toxicity to organisms, has teratogenic effect and has certain toxic and side effects on inheritance, development and reproduction of the organisms, so that the detection of glyphosate residues in foods is enhanced in various countries in recent years.
Currently, glyphosate residue detection methods include chemical analysis, spectrophotometry, high performance liquid chromatography, gas chromatography, chromatography-mass spectrometry, and rapid methods such as enzyme-linked immunosorbent assay, electrochemical analysis, and the like. In the methods, a chromatographic method and a mass spectrometry method are combined to obtain good effects, but the methods have the defects of complex pretreatment, long detection time, difficulty in high-throughput analysis and certain limitation on popularization and application. The rapid detection technologies such as immunodetection, electrochemical detection and the like are late in starting and are still immature in development. Therefore, a rapid detection method with high sensitivity, strong specificity and strong universality is innovated, and a powerful technical support can be provided for the safety detection and monitoring of glyphosate.
Compared with the detection method, the fluorescence sensing detection method has the advantages of easily available equipment, simple operation, low requirement on personnel, high sensitivity, strong specificity, short response time, real-time detection, naked eye identification and field analysis, and therefore the method is rapidly developed in the field of analysis and detection. The fluorescent sensing detection method is applied to the detection of glyphosate residues, and has wide application prospect.
Disclosure of Invention
The method is used for constructing the zinc ion-mediated fluorescence sensor and detecting the glyphosate, and can solve the defects of complex sample treatment, long time consumption, high cost and difficulty in large-scale conventional detection in the existing glyphosate detection method.
The preparation method of the zinc ion-mediated fluorescence sensor comprises the following steps:
dissolving fluorescent probe in organic solvent/HEPES buffer solvent to obtain 3.0X10 -5 Adding inorganic zinc salt into the mol/L solution, and incubating for 2-4 min to obtain the fluorescent sensor.
The structural formula of the fluorescent probe is as follows:
the fluorescent probe is prepared by condensation reaction of salicylaldehyde hydrazone and aromatic aldehyde.
Preferably, the aromatic aldehyde in the preparation method can be quinoline-8-formaldehyde, 6-methoxy-2-naphthalene aldehyde, anisaldehyde, benzothiophene-2-carboxyaldehyde, quinoline-2-formaldehyde or o-vanillin.
Preferably, the organic solvent/HEPES buffer solvent in the step, the organic solvent may be DMSO, DMF, acetone or methanol.
Further, the molar ratio of zinc ions to fluorescent probe is 1 (2-3), preferably 1:2.2.
Preferably, the inorganic zinc salt in the step may be zinc nitrate, zinc sulfate, zinc acetate or zinc chloride, preferably zinc acetate.
The fluorescence sensor prepared by the method can be applied to qualitative and quantitative detection of glyphosate.
When the invention is actually used for detecting the glyphosate-containing sample, the sample is subjected to pretreatment of soaking, centrifugation and filtration.
The principle of the invention is as follows: the fluorescent probe prepared by the invention has a conjugated system and a rigid planar structure, and does not have fluorescence. The hydroxyl, imine bond and N heteroatom in the probe structure can be complexed with zinc ions to form a complex, so that electrons are transferred to metal ions to generate a fluorescence effect. The glyphosate molecule contains amino, phosphate, carboxyl and other functional groups, and the functional groups and zinc ions have strong coordination, so that the zinc ions in the complex can be replaced, the probe is recovered to a monomer state, the electron transfer function disappears, and fluorescence disappears, so that the fluorescence detection of the glyphosate is realized. The principle of the fluorescent sensor for identifying the glyphosate is shown in figure 1.
Compared with the prior art, the invention has the advantages that:
(1) The invention uses the zinc ion-mediated fluorescence sensor for glyphosate detection for the first time. The sensor itself has fluorescence, and exhibits a fluorescent ON state. After identifying the glyphosate, the fluorescence disappears, and the fluorescence is in an OFF state, so that the ON-OFF detection of the glyphosate is realized.
(2) The fluorescence sensor constructed by the invention has obvious color/fluorescence change in the process of detecting the glyphosate under the visible light/ultraviolet light, thereby realizing the visual detection of the glyphosate.
(3) The fluorescence sensor constructed by the invention has the linear relation between the fluorescence intensity and the concentration of glyphosate in the concentration of 0-12 mu mol/L (0-2.0 mu g/mL) and the detection limit of 3.8X10 -8 mol/L (6.42 ng/mL), and can realize the trace detection of the glyphosate.
(4) The fluorescence sensor constructed by the invention has the advantages of simple preparation method, good product purity, high yield, low cost and good commercialization prospect.
(5) The fluorescent sensor prepared by the invention has good selectivity for identifying the glyphosate, can not be interfered by other organophosphorus pesticides, is simple and convenient to operate, does not need expensive large-scale instruments and complex sample pretreatment, and can realize large-scale and conventional detection of the glyphosate.
Drawings
FIG. 1 fluorescent probe L1 1 H NMR spectrum;
FIG. 2 fluorescent probe L1 13 C NMR spectrum;
FIG. 3 IR spectrum of fluorescent probe L1;
FIG. 4 shows a zinc ion selective recognition pattern of the fluorescent probe L1;
FIG. 5 is a plot of fluorescent probe L1 versus Job's plot of zinc ions;
FIG. 6 is a graph of fluorescence sensor versus glyphosate selective recognition;
FIG. 7 fluorescent probe L1 (1 #) and fluorescent sensor L-Zn at 365nm ultraviolet light 2+ (2 #) fluorescent sensor L-Zn 2+ Fluorescent sensor L-Zn which is respectively reacted with glyphosate (3 #), trichlorfon (4 #), iminothiolane (5 #), dichlorvos (6 #), malathion (7 #), omethoate (8 #), dimethoate (9 #), acephate (10 #), fenitrothion (11 #), methyl parathion (12 #), parathion (13 #), and glufosinate (14 #) 2+ A fluorescence change map;
FIG. 8 fluorescence sensor recognizes glyphosate anti-interference ability profile;
FIG. 9 is a graph of fluorescence sensor versus glyphosate concentration;
FIG. 10 is a graph of fluorescence sensor recognition glyphosate UV-visible absorption spectra;
FIG. 11 is a Job's plot of fluorescence sensor versus glyphosate;
FIG. 12 is a graph of a reversible cycle experiment of a fluorescence sensor recognizing glyphosate;
FIG. 13 is a schematic diagram of a fluorescence sensor identifying glyphosate;
Detailed Description
The technical scheme of the invention is not limited to the specific embodiments listed below, and also includes any combination of the specific embodiments.
The first embodiment is as follows: the zinc ion-mediated fluorescence sensor for glyphosate detection in the embodiment is prepared by the following steps:
dissolving the fluorescent probe inIn organic solvent/HEPES buffer solvent, 3.0X10 -5 Adding inorganic zinc salt into the mol/L solution, and incubating for 2-4 min to obtain the fluorescent sensor.
The second embodiment is as follows: the first difference between this embodiment and the specific embodiment is that: the fluorescent probe structure is one of the following structures. The other is the same as in the first embodiment.
And a third specific embodiment: this embodiment differs from the first or second embodiment in that: the fluorescent probe is prepared by condensation reaction of salicylaldehyde hydrazone and aromatic aldehyde. The other is the same as the first or second embodiment.
The specific embodiment IV is as follows: the third difference between this embodiment and the third embodiment is that: the aromatic aldehyde used in the preparation of the fluorescent probe is one of quinoline-8-formaldehyde, 6-methoxy-2-naphthalene aldehyde, anisaldehyde, benzothiophene-2-carboxyaldehyde, quinoline-2-formaldehyde or o-vanillin. The other is the same as in the third embodiment.
Fifth embodiment: the first difference between this embodiment and the specific embodiment is that: in the organic solvent/HEPES buffer solvent, the organic solvent is one of DMSO, DMF, acetone or methanol. The other is the same as in the first embodiment.
Specific embodiment six: the first difference between this embodiment and the specific embodiment is that: the mole ratio of zinc ion to fluorescent probe is 1 (2-3). The other is the same as in the first embodiment.
Seventh embodiment: the first difference between this embodiment and the specific embodiment is that: the molar ratio of zinc ions to fluorescent probe was 1:2.2. The other is the same as in the first embodiment.
Eighth embodiment: the first difference between this embodiment and the specific embodiment is that: the inorganic zinc salt used in the construction of the sensor is one of zinc nitrate, zinc sulfate, zinc acetate or zinc chloride. The other is the same as in the first embodiment.
Detailed description nine: the zinc ion fluorescence sensing system is used for qualitative and quantitative detection of glyphosate.
The following examples of the present invention are described in detail, and are provided by taking the technical scheme of the present invention as a premise, and the detailed embodiments and specific operation procedures are given, but the scope of the present invention is not limited to the following examples.
Example 1: preparation of fluorescent Probe L1
Into a three-necked flask, yang Quanzong 0.1.1 g of water, 0.12g of quinoline-8-carbaldehyde and 30mL of ethanol were added, and the mixture was refluxed with a little glacial acetic acid for 6 hours. Filtering while the solution is hot, recrystallizing with ethanol, and vacuum drying to obtain fluorescent probe L1.16 g with a yield of 79.1%. 1 H NMR(300MHz,DMSO-d 6 )δ11.33(s,1H),9.89(s,1H),9.16–8.88(m,2H),8.50(td,J＝8.3,7.5,1.6Hz,2H),8.20(dd,J＝8.2,1.5Hz,1H),7.87–7.70(m,2H),7.66(dd,J＝8.3,4.2Hz,1H),7.41(ddd,J＝8.7,7.3,1.7Hz,1H),7.06–6.81(m,2H). 13 C NMR(75MHz,DMSO-d 6 )δ163.79,159.30,159.23,151.38,146.28,137.22,133.62,132.31,131.65,130.55,128.53,127.57,126.97,122.60,120.02,118.69,116.95ppm.FT-IR(KBr)：3440.71,1619.64,1572.22,1493.98,830.21,788.82,752.09,730.57,650.88cm -1 . Fluorescent probe L1 1 H NMR spectrum, 13 The C NMR spectrum and the IR spectrum are shown in FIGS. 1, 2 and 3, respectively.
Example 2: preparation of fluorescent Probe L2
This example is different from example 1 in that the aromatic aldehyde used in the reaction is 6-methoxy-2-naphthaldehyde, and the remainder is the same as example 1. The yield thereof was found to be 85.2%. 1 H NMR(300MHz,DMSO-d 6 )δ11.38(s,1H),8.99(s,1H),8.90(s,1H),8.27(d,J＝1.5Hz,1H),8.02(dd,J＝8.6,1.6Hz,1H),7.93(dd,J＝11.4,8.8Hz,2H),7.76–7.64(m,1H),7.51–7.32(m,2H),7.24(dd,J＝8.9,2.5Hz,1H),7.08–6.91(m,2H),3.91(s,3H). 13 C NMR(75MHz,DMSO-d 6 )δ163.29,162.94,159.26,159.14,136.62,133.43,131.68,131.44,130.81,129.42,128.46,127.98,124.31,119.99,119.83,118.70,116.91,106.88,55.85ppm.FT-IR(KBr)3423.84,1619.98,1600.51,1484.35,1384.79,1275.70,1178.40,1198.16,1021.11,967.99,858.67,747.33cm -1 .
Example 3: preparation of fluorescent Probe L3
This example is different from example 1 in that the aromatic aldehyde used in the reaction is anisaldehyde, and the remainder is the same as example 1. The yield thereof was found to be 74.9%. 1 H NMR(300MHz,DMSO-d 6 )δ11.14(s,1H),9.01(s,1H),8.63(s,1H),7.82(t,J＝8.9Hz,2H),7.67(ddd,J＝13.2,7.9,1.6Hz,1H),7.39(dtd,J＝7.9,6.7,6.2,1.7Hz,1H),7.06(dd,J＝8.7,6.7Hz,2H),7.01–6.86(m,2H),3.82(d,J＝2.7Hz,3H).13C NMR(75MHz,DMSO-d6)δ163.24,162.10,160.98,159.09,133.69,131.27,130.43,127.01,120.05,118.64,116.98,114.84,55.83ppm.FT-IR(KBr)3432.01,1624.45,1568.67,1487.34,1454.26,1384.79,1298.98,1276.89,1250.40,1204.99,1168.22,1111.01,1025.20,894.44,829.06,775.94,751.76cm -1 .
Example 4: preparation of fluorescent Probe L4
This example differs from example 1 in that the aromatic aldehyde used in the reaction is benzothiophene-2-carboxaldehyde, the remainder being the same as in example 1. The yield thereof was found to be 86.4%. 1 H NMR(300MHz,DMSO-d 6 )δ11.22(s,1H),9.12(s,1H),8.97(s,1H),8.07–8.00(m,2H),8.00–7.87(m,1H),7.70(dd,J＝8.0,1.7Hz,1H),7.43(dtd,J＝15.6,8.5,7.9,1.7Hz,3H),7.09–6.71(m,2H). 13 C NMR(75MHz,DMSO-d 6 )δ163.83,159.22,157.61,140.65,139.50,138.92,133.73,132.01,131.63,127.36,125.50,125.48,123.30,120.04,118.63,116.97.FT-IR(KBr)：3421.01,3051.11,2925.07,1614.70,1584.73,1491.45,1286.94,1271.03,1230.55,1166.52,1040.27,947.75,871.61,788.93,745.27,736.90cm -1 .
Example 5: preparation of fluorescent Probe L5
This example is different from example 1 in that the aromatic aldehyde used in the reaction is quinoline-2-carbaldehyde, and the remainder is the same as example 1. The yield thereof was found to be 89.1%. 1 H NMR(300MHz,DMSO-d 6 )δ11.09(s,1H),9.05(s,1H),8.83(s,1H),8.50(d,J＝8.6Hz,1H),8.22(d,J＝8.6Hz,1H),8.09(dd,J＝16.3,8.2Hz,2H),7.84(t,J＝7.7Hz,1H),7.77(d,J＝8.0Hz,1H),7.69(d,J＝7.3Hz,1H),7.43(t,J＝8.3Hz,1H),7.05–6.98(m,2H). 13 C NMR(75MHz,DMSO-d 6 )δ164.34,162.48,159.30,153.29,147.99,137.48,134.05,131.40,130.79,129.70,128.80,128.54,128.46,120.05,118.84,118.66,117.06.ppm.FT-IR(KBr)3432.01,1623.36,1590.17,1500.04,1478.03,1425.98,1372.53,1311.24,1272.75,1115.10,1198.36,1147.79,1033.37,962.56,886.27,836.01,751.50,788.20,757.50cm -1 .
Example 6: preparation of fluorescent Probe L6
This example differs from example 1 in that the aromatic aldehyde used in the reaction is o-vanillin, the remainder being the same as example 1. The yield thereof was found to be 75.8%. 1 H NMR(300MHz,DMSO-d 6 )δ11.13(s,1H),10.91(s,1H),9.00(d,J＝2.5Hz,2H),7.70(dd,J＝7.7,1.7Hz,1H),7.40(ddd,J＝8.6,7.3,1.7Hz,1H),7.28(dd,J＝7.9,1.4Hz,1H),7.12(dd,J＝8.1,1.5Hz,1H),7.03–6.86(m,3H),3.83(s,3H).13C NMR(75MHz,DMSO-d6)δ163.30,163.19,159.10,148.94,148.40,133.68,131.30,122.49,120.04,119.73,118.79,118.64,116.98,115.70,56.32ppm.FT-IR(KBr)3432.01,1623.36,1590.17,1500.04,1478.03,1425.98,1372.53,1311.24,1272.75,1115.10,1198.36,1147.79,1033.37,962.56,886.27,836.01,751.50,788.20,757.50.
Example 7: the fluorescent probe L1 specifically recognizes metal ions, and the method comprises the following steps:
respectively taking 3mL of the mixture with the concentration of 3.0X10 -5 mol/L probe L1 DMSO/HEPES buffer solution was added at a concentration of 3X 10 in 10. Mu.L -2 Co of mol/L 2+ 、Zn 2+ 、Cs + 、Ca 2+ 、Cr 3+ 、K + 、Ni 2+ 、Al 3+ 、Fe 3+ 、Mg 2+ 、Pb 2+ 、Na + 、Ba 2+ 、Ce 3+ 、Ag + 、Cu 2+ 、Cd 2+ And Hg of 2+ The solution, fluorescence emission peak intensity at 540nm, is shown in FIG. 4.
In FIG. 4, zn is present in the probe L1 system 2+ When the system fluorescence is obviously enhanced, the fluorescence intensity is increased from 8a.u to 903a.u, 112 times is enhanced, other ions are added without obvious change, and the probe can be used for Zn 2+ Characteristic response, and zinc ions to construct a fluorescence sensor.
Example 8: the action proportion of the fluorescent probe L1 and zinc ions is carried out according to the following steps:
the total concentration of the probe L1 and zinc ions was kept constant at 30. Mu. Mol/L during the measurement by the equimolar continuous change method, and the fluorescence response value at the emission wavelength of 540nm was plotted on the ordinate and the molar concentration of zinc ions on the abscissa, and the result is shown in FIG. 5. When the concentration of zinc ions is 0.34, inflection points appear in the fluorescence intensity of the system, and Zn can be obtained based on the inflection points 2+ The action ratio of the probe to the probe is 1:2.
Example 9: the construction of the fluorescence sensor is carried out according to the following steps:
100mL of the solution was taken to have a concentration of 3.0X10 -5 1.5X10 mol/L of probe solution was added -5 Incubating zinc acetate in mol/L for 2-4 min to obtain zinc ion mediated fluorescence sensor (1.5X10) -5 mol/L) for later use.
Example 10: the fluorescent sensor is used for selectively identifying the glyphosate, and the method comprises the following steps:
3mL of fluorescence sensor was taken and sequentially added 1.5X10 -5 The fluorescence intensity of the mol/L glyphosate, trichlorfon, iminothiolane, dichlorvos, malathion, omethoate, dimethoate, acephate, fenitrothion, methyl parathion, parathion and glufosinate is measured under the excitation light effect of 425 nm. The results are shown in FIG. 6. And the naked eye recognition condition of the fluorescent sensor on the glyphosate is observed under ultraviolet light, as shown in figure 7.
As shown in FIG. 6, when the fluorescent sensor is used for identifying the glyphosate, the fluorescent intensity is obviously weakened and is consistent with that of the initial probe L1, and the fluorescent signal intensity of the sensor is not obviously changed when other 11 pesticides are added, so that the fluorescent sensor can be used for realizing characteristic identification of the glyphosate, and the fluorescent intensity of a system is restored to the initial value of the probe.
As shown in FIG. 7, when the fluorescence of the system is obviously quenched after the glyphosate is added, the fluorescence intensity of the system (3 # is recovered to the initial state (1 #) of the probe after the glyphosate is added into the fluorescence sensor (2 #), and other organophosphorus pesticides (4 # to 14 #) are added, so that no fluorescence phenomenon is generated. According to the analysis, the sensing system realizes specific identification of the glyphosate, and can realize macroscopic observation of the glyphosate.
Example 11: the fluorescent sensor has the anti-interference performance on glyphosate identification, and the method comprises the following steps:
3mL of fluorescence sensor was added sequentially to 1.5X10 -5 mol/L glyphosate, trichlorfon, iminothiolane, dichlorvos, malathion, omethoate, dimethoate, acephate, fenitrothion, methyl parathion, parathion and glufosinate, and recording the fluorescence intensity under the excitation light of 425 nm. Then sequentially adding 1.5X10 -5 The change in fluorescence intensity was observed and recorded for mol/L glyphosate, and the results are shown in FIG. 8.
When the sensor singly recognizes 12 organophosphorus pesticides, and only glyphosate is added, the sensing system generates obvious fluorescence quenching response, and the addition of other 11 pesticides hardly affects the fluorescence intensity of the sensor. When the glyphosate respectively coexists with other 11 organophosphorus pesticides, the detection system has obvious phenomenon of weakening of fluorescent signals, so that the sensor can recognize the glyphosate and the existence of other pesticides can not influence the detection of the glyphosate.
Example 12: the fluorescence sensor detects the limit of glyphosate, and the method comprises the following steps:
3mL of zinc ion fluorescence sensor was used, 1. Mu.L of the zinc ion fluorescence sensor was added each time at a concentration of 3X 10 -3 The fluorescence intensity of the aqueous solution of mol/L glyphosate was measured, and the result is shown in FIG. 9.
When the glyphosate is added into the sensing system in a gradient way, the fluorescence response value gradually decreases along with the increase of the concentration of the glyphosate, when the concentration of the glyphosate is in the range of 0-12 mu mol/L (namely 0-2 mu g/mL), the fluorescence response value of the sensor is in a linear relation with the concentration of the glyphosate, and the curve fitting equation is Y= -67.44X+906.4, R 2 =0.9982, and the detection limit of the sensor to glyphosate is calculated to be 3.8x10 according to the calculation formula 3 sigma/k of the detection limit -8 mol/L (i.e., 6.42 ng/mL), thus the constructed fluorescence sensor can realize the trace detection of glyphosate.
Example 13: the action mechanism of the fluorescence sensor on the glyphosate is carried out according to the following steps:
the ultraviolet-visible absorption spectra of probe L1, fluorescence sensor and fluorescence sensor after glyphosate addition were separately tested, as shown in FIG. 10.
From the graph analysis, the initial state probe L1 has ultraviolet absorption at 355nm, and when the probe recognizes zinc ions, the maximum ultraviolet absorption peak at 355nm is red shifted to 416 nm. When the sensor recognizes glyphosate, the absorption peak at 416nm disappears and transitions back to 355nm, which is the same as the absorption peak of the initial state probe L1. It is inferred from this that after the fluorescent sensor recognizes glyphosate, the strong chelation of zinc ions by the glyphosate molecule causes the sensor to lose zinc ions and revert to the free probe L1 state.
Example 14: the action ratio of the fluorescence sensor to the glyphosate is carried out according to the following steps:
the total concentration of the sensor and the glyphosate is kept to be 15 mu mol/L, the molar concentration ratio of the sensor and the glyphosate in the system is changed, the fluorescence change of the system is measured, and a Job's plot curve is drawn, as shown in figure 11.
When the molar concentration ratio of the glyphosate is between 0 and 0.5, the fluorescence intensity is reduced sharply along with the increase of the molar concentration of the glyphosate in the system. When the molar concentration ratio of the glyphosate is between 0.5 and 0.9, the fluorescence intensity is slowly weakened along with the increase of the molar concentration of the glyphosate in the system. Thus, the inflection point of the change in fluorescence intensity appears at a glyphosate concentration of 0.48, resulting in a 1:1 ratio of fluorescence sensor to glyphosate.
Example 15: reversible cycle experiment for identifying glyphosate by fluorescent sensor
In the fluorescence sensor solution, equal amounts of glyphosate and zinc ions were alternately added, fluorescence intensity changes were recorded and a cycle curve was made, as shown in fig. 12.
The fluorescence intensity is still kept at 95% after five times of experiments, so that the sensor can realize alternative fluorescence identification of glyphosate and zinc ions. Meanwhile, the mechanism of the sensor for identifying the glyphosate is verified, namely the glyphosate can chelate zinc ions in the sensor, so that the detection system is restored to the initial state of the probe. From this, it is inferred that the mechanism by which the fluorescence sensor recognizes glyphosate is as shown in FIG. 13.
Example 16: fluorescent sensor applied to glyphosate detection in tea
Taking commercially available Longjing tea leaves for pretreatment: weighing 0.5g of tea leaves, placing the tea leaves into a centrifuge tube, adding 50mL of water immersed tea leaf sample, carrying out ultrasonic oscillation for 20min, and centrifuging at 4000r/min for 10min. Transferring the supernatant into another plastic centrifuge tube, repeatedly extracting the residue with 20mL of water, mixing the aqueous solutions, and filtering with 0.45 μm filter to obtain the following solutions with the concentrations of: the samples were tested using the constructed sensors with 0.3. Mu.g/mL, 0.6. Mu.g/mL, 0.9. Mu.g/mL, 1.5. Mu.g/mL glyphosate solution. Under the action of 425nm excitation light, the fluorescence emission peak intensity of the fluorescence sensing system at 540nm is measured and brought into the following equation, and the concentration of glyphosate is calculated, and the result is shown in table 1.
Y＝-67.44X+906.4
Wherein X is the concentration of glyphosate, and Y is the fluorescence emission peak intensity value.
TABLE 1 fluorescent sensor for detection of glyphosate in tea leaves
The data show that the standard adding recovery rate of the glyphosate in the actual tea leaves is 98.1-104.6%, the relative standard deviation is 0.48-3.28%, and the error between the detected glyphosate concentration and the corresponding standard adding concentration is smaller. The sensor has high accuracy in detecting the glyphosate in the actual tea samples, and the sensor system has a certain application prospect in the field of food analysis and detection.
Claims (5)
1. The preparation method of the zinc ion-mediated fluorescence sensor is characterized by comprising the following steps of:
dissolving fluorescent probe in organic solvent/HEPES buffer solvent to obtain 3.0X10 -5 Adding inorganic zinc salt into the mol/L solution, and incubating for 2-4 min to obtain a fluorescence sensor;
the structural formula of the fluorescent probe is one of the following:
wherein, the mol ratio of zinc ion to fluorescent probe is 1 (2-3).
2. The method for preparing the zinc ion-mediated fluorescence sensor according to claim 1, wherein the fluorescence probe is prepared by condensation reaction of salicylaldehyde hydrazone and aromatic aldehyde, wherein the aromatic aldehyde is quinoline-8-formaldehyde, 6-methoxy-2-naphthalene aldehyde, anisaldehyde, benzothiophene-2-carboxamide, quinoline-2-formaldehyde or o-vanillin.
3. The method for preparing the zinc ion-mediated fluorescence sensor according to claim 1, wherein the organic solvent is DMSO, DMF, acetone or methanol in the organic solvent/HEPES buffer solvent.
4. The method for preparing a zinc ion-mediated fluorescence sensor according to claim 1, wherein the inorganic zinc salt in the step is zinc nitrate, zinc sulfate, zinc acetate or zinc chloride.
5. The fluorescent sensor prepared by the preparation method of the fluorescent sensor as claimed in claim 1 is applied to qualitative and quantitative detection of glyphosate in tea.
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