CN107384373B - One kind having selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof - Google Patents

One kind having selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof Download PDF

Info

Publication number
CN107384373B
CN107384373B CN201710543173.1A CN201710543173A CN107384373B CN 107384373 B CN107384373 B CN 107384373B CN 201710543173 A CN201710543173 A CN 201710543173A CN 107384373 B CN107384373 B CN 107384373B
Authority
CN
China
Prior art keywords
crystal material
luminescent crystal
added
oba
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201710543173.1A
Other languages
Chinese (zh)
Other versions
CN107384373A (en
Inventor
夏友付
沈悦
王清
常永侠
杨永建
曹帅
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to CN201710543173.1A priority Critical patent/CN107384373B/en
Publication of CN107384373A publication Critical patent/CN107384373A/en
Application granted granted Critical
Publication of CN107384373B publication Critical patent/CN107384373B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00Compounds containing elements of Groups 2 or 12 of the Periodic System
    • C07F3/06Zinc compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/008Supramolecular polymers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18Metal complexes
    • C09K2211/188Metal complexes of other metals not provided for in one of the previous groups

Abstract

The invention discloses one kind to have selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof, the chemical formula of the luminescent crystal material are [Zn (OBA) (3-abit)]n, belong to anorthic system, space group P-1, cell parameter is α=73.382 (2) °, β=76.088 (2) °, γ=80.229 (2) °, Z=2.Its preparation process is the following steps are included: by zinc nitrate and 4, 4 '-oxydibenzoic acids are added in aqueous solution stirring, by 4- amino -3, 5- bis- (imidazolmethyl) -1, 2, 4- triazole, which is added in methanol solution, to be stirred, by zinc nitrate obtained above and 4, the aqueous solution of 4 '-oxydibenzoic acids is placed in reaction tube and buffer solvent is added, again by 4- amino -3, 5- bis- (imidazolmethyl) -1, 2, the methanol solution of 4- triazole is slowly added into reaction tube, through crystallizing after sealing, filtering, washing, drying to obtain luminescent crystal material [Zn (OBA) (3-abit)]n.Luminescent crystal material prepared by the present invention is to Fe3+The selective Effect on Detecting of ion, and the chemistry of luminescent crystal material, optical stability are good.

Description

One kind having selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof
Technical field
The present invention relates to the preparations of metal cation detection material, and in particular to one kind has selectivity detection Fe3+Ion Luminescent crystal material and preparation method thereof.
Background technique
With the fast development of global industry, iron and its alloy have become in the world using most a kind of metal materials Material, since it is with numerous good performances, makes it be widely used in the national economy such as machinework, catalyst, metallurgical product Every field, provide strong advantageous support for economic development.Meanwhile ferro element is also the essential element for constituting human body One of, it is not only the pith of hemoglobin or the ingredient of many enzymes and immune system compound, and can participate in The transport and storage of oxygen, play an important role human health.However, the fast development of industry results in a large amount of Fe3+From Son is discharged into environment water, is caused and is seriously threatened to environment etc.;Simultaneously in human body, iron deficiency and Fe supply can be to them Cause very big injury, such as anaemia, heart and liver diseases, diabetes.Therefore effective detection Fe3+Ion pair environment and Human health is extremely important.In reported various Detection Techniques, the chemistry based on fluorescence coordination polymer Sensing is since it has the characteristics that high sensitivity and highly selective, cheap and easy to get, easy flexible has become current numerous scientific research people The emphasis of member's research.Such as document Dalton Trans., 2013,42,12403-12409 and Inorg.Chem.2016,55, 3952-3959 is reported with Fe3+The luminous complex of ion detection performance.
Summary of the invention
In order to solve the above technical problems, the present invention, which provides one kind, has selectivity detection Fe3+The luminescent crystal material of ion And preparation method thereof;Used technical solution are as follows:
It is described that there is selectivity detection Fe3+The luminescent crystal material of ion, chemical formula are [Zn (OBA) (3-abit)]n, Belong to anorthic system, space group P-1, cell parameter isα= 73.382 (2) °, β=76.088 (2) °, γ=80.229 (2) °, Z=2.The crystalline material structure as shown in Figure 1, be by The one-dimensional trapezoidal skeleton structure of one kind made of the Zn of four connections and two kinds of bridge ligands OBA, 3-abit are constructed.
Further, the luminescent crystal material preparation method the following steps are included:
(1) by zinc nitrate and 4,4 '-oxydibenzoic acids (OBA) are added in aqueous solution, and are stirred 3-6 minutes, and be added Alkaline solution adjusts pH to 6-8;
(2) two (imidazolmethyl) -1,2,4- triazole (3-abit) of 4- amino -3,5- is added in methanol solution and is stirred It mixes 5-7 minutes;
(3) solution obtained in step (1) is placed in reaction tube, and buffer solvent is added, be slowly added in step (2) Obtained solution is crystallized after sealing, is filtered, washed, drying to obtain luminescent crystal material [Zn (OBA) (3-abit)]n
Further, provided by the invention that there is selectivity detection Fe3+In the preparation method of the luminescent crystal material of ion, Start material zinc nitrate, 4,4 '-oxydibenzoic acids, 4- amino -3,5- bis- (imidazolmethyl) -1, mole of 2,4- triazoles Than for 1:0.5~1:0.5~1.
Further, provided by the invention that there is selectivity detection Fe3+The preparation method of the luminescent crystal material of ion In, the buffer solvent is CH3OH and H2The mixed solution of O, wherein CH3OH and H2The volume ratio of O is 1:0.5~1.
The luminescent crystal material provided through the invention is not only to Fe3+The selective Effect on Detecting of ion generates Fluorescence intensity apparent quenching effects occur, and effect is not quenched to the fluorescence intensity of other metal cations significantly then Fruit, and the chemistry of luminescent crystal material, optical stability are good;It is not only reacted in the preparation process of luminescent crystal material simultaneously Beginning object is cheap and easy to get, and cost is relatively low, and preparation condition is mild, easily controllable.It is detected by X-ray diffraction pattern, the present invention Prepared luminescent crystal material [Zn (OBA) (3-abit)]nPowder x-ray diffraction pattern and theoretical calculation X-ray Diffraction pattern is almost the same, illustrates crystalline material prepared by the present invention [Zn (OBA) (3-abit)]nWith very high purity.
Detailed description of the invention
Fig. 1 is luminescent crystal material [Zn (OBA) (3-abit)] of the inventionnOne-dimentional structure figure;
Fig. 2 is luminescent crystal material [Zn (OBA) (3-abit)] of the inventionnOne-dimentional structure figure partial enlarged view;
The luminescent crystal material [Zn (OBA) (3-abit)] that Fig. 3 is 1 milligramnVolume is 3 milliliters, solubility is 0.01 to rub You/liter metal cation aqueous solution in fluorescence spectra (excitation wavelength 350nm);
Fig. 4 is the corresponding fluorescence column diagram of Fig. 3 fluorescence spectra;
Fig. 5 is luminescent crystal material [Zn (OBA) (3-abit)] of the inventionnPowder X-ray diffractogram.
Specific embodiment
Preparation method of the present invention is described further below in conjunction with attached drawing and specific embodiment.
Embodiment 1:
1, the preparation of luminescent crystal material: the following steps are included:
(1) the 4,4 '-oxydibenzoic acids (OBA) of the zinc nitrate of 0.1mmol and 0.1mmol are added to the water-soluble of 5mL It is stirred 4 minutes in liquid, and sodium hydroxide solution is added and adjusts pH to 6;(2) by two (the imidazoles first of 4- amino -3,5- of 0.1mmol Base) -1,2,4- triazoles (3-abit) are added in the methanol solution of 5mL, are stirred 6 minutes;It (3) will be obtained in step (1) Solution is placed in the CH that 3mL in reaction tube and is added3OH and H2O buffer solvent, the wherein CH of buffer solvent3OH and H2The volume ratio of O For 1:1, then solution obtained in step (2) is added in reaction tube, crystallized, is filtered, washed after sealing, drying to obtain hair Luminescent crystal material [Zn (OBA) (3-abit)] n;
2、Fe3+The test of ion selectivity detection performance: it is 3 that the luminescent crystal material (1 milligram) of preparation, which is added to volume, In milliliter, the metal cation aqueous solution that solubility is 0.01 mol/L, then ultrasonic two hours obtained stable suspensions exist The fluorescence spectrum of different cationic aqueous solutions is measured under 350nm exciting light.
As shown in Figure 3 and Figure 4, luminescent crystal material provided by the invention to the fluorescence spectrum of different metal cation respectively not It is identical, wherein to Fe3+Ion is far below other metal cations, selective Effect on Detecting, the fluorescence intensity generated Apparent quenching effects occur, and to the fluorescence intensity of other metal cations then without apparent quenching effects.
3, X-ray diffraction is analyzed: being put into X-ray diffractometer and is carried out to the powder of the luminescent crystal material (5mg) of preparation Diffraction pattern analysis.
As shown in figure 5, being detected by X-ray diffraction pattern, luminescent crystal material [Zn (OBA) prepared by the present invention (3-abit)]nX-ray diffraction pattern and theoretical calculation X-ray diffraction pattern it is almost the same, illustrate prepared by the present invention Crystalline material [Zn (OBA) (3-abit)]nWith very high purity.
Embodiment 2:
1, the preparation of luminescent crystal material: the following steps are included:
(1) the 4,4 '-oxydibenzoic acids (OBA) of the zinc nitrate of 0.1mmol and 0.05mmol are added to the water-soluble of 5mL It is stirred 5 minutes in liquid, and sodium hydroxide solution is added and adjusts pH to 6;(2) by two (the imidazoles first of 4- amino -3,5- of 0.05mmol Base) -1,2,4- triazoles (3-abit) are added in the methanol solution of 5mL, are stirred 5 minutes;It (3) will be obtained in step (1) Solution is placed in the CH that 3mL in reaction tube and is added3OH and H2O buffer solvent, the wherein CH of buffer solvent3OH and H2The volume ratio of O For 1:0.5, then solution obtained in step (2) is added in reaction tube, crystallized, is filtered, washed after sealing, drying to obtain Luminescent crystal material [Zn (OBA) (3-abit)] n;
2、Fe3+The test of ion selectivity detection performance: it is 3 that the luminescent crystal material (1 milligram) of preparation, which is added to volume, In milliliter, the metal cation aqueous solution that solubility is 0.01 mol/L, then ultrasonic two hours obtained stable suspensions exist The fluorescence spectrum of different cationic aqueous solutions is measured under 350nm exciting light.
3, X-ray diffraction is analyzed: luminescent crystal material (5mg) powder of preparation being put into X-ray diffractometer and is spread out Penetrate Interferogram Analysis.
Embodiment 3:
1, the preparation of luminescent crystal material: the following steps are included:
(1) the 4,4 '-oxydibenzoic acids (OBA) of the zinc nitrate of 0.1mmol and 0.05mmol are added to the water-soluble of 5mL It is stirred 5 minutes in liquid, and sodium hydroxide solution is added and adjusts pH to 7;(2) by two (the imidazoles first of 4- amino -3,5- of 0.1mmol Base) -1,2,4- triazoles (3-abit) are added in the methanol solution of 5mL, are stirred 5 minutes;It (3) will be obtained in step (1) Solution is placed in the CH that 3mL in reaction tube and is added3OH and H2O buffer solvent, the wherein CH of buffer solvent3OH and H2The volume ratio of O For 1:1, then solution obtained in step (2) is added in reaction tube, crystallized, is filtered, washed after sealing, drying to obtain hair Luminescent crystal material [Zn (OBA) (3-abit)] n;
2、Fe3+The test of ion selectivity detection performance: it is 3 that the luminescent crystal material (1 milligram) of preparation, which is added to volume, In milliliter, the metal cation aqueous solution that solubility is 0.01 mol/L, then ultrasonic two hours obtained stable suspensions exist The fluorescence spectrum of different cationic aqueous solutions is measured under 350nm exciting light.
3, X-ray diffraction is analyzed: luminescent crystal material (5mg) powder of preparation being put into X-ray diffractometer and is spread out Penetrate Interferogram Analysis.
Embodiment 4:
1, the preparation of luminescent crystal material: the following steps are included:
(1) the 4,4 '-oxydibenzoic acids (OBA) of the zinc nitrate of 0.1mmol and 0.05mmol are added to the water-soluble of 5mL It is stirred 5 minutes in liquid, and sodium hydroxide solution is added and adjusts pH to 7;(2) by two (the imidazoles first of 4- amino -3,5- of 0.05mmol Base) -1,2,4- triazoles (3-abit) are added in the methanol solution of 5mL, are stirred 5 minutes;It (3) will be obtained in step (1) Solution is placed in the CH that 3mL in reaction tube and is added3OH and H2O buffer solvent, the wherein CH of buffer solvent3OH and H2The volume ratio of O For 1:0.5, then solution obtained in step (2) is added in reaction tube, crystallized, is filtered, washed after sealing, drying to obtain Luminescent crystal material [Zn (OBA) (3-abit)] n;
2、Fe3+The test of ion selectivity detection performance: it is 3 that the luminescent crystal material (1 milligram) of preparation, which is added to volume, In milliliter, the metal cation aqueous solution that solubility is 0.01 mol/L, then ultrasonic two hours obtained stable suspensions exist The fluorescence spectrum of different cationic aqueous solutions is measured under 350nm exciting light.
3, X-ray diffraction is analyzed: luminescent crystal material (5mg) powder of preparation being put into X-ray diffractometer and is spread out Penetrate Interferogram Analysis.
Embodiment 5:
1, the preparation of luminescent crystal material: the following steps are included:
(1) the 4,4 '-oxydibenzoic acids (OBA) of the zinc nitrate of 0.1mmol and 0.1mmol are added to the water-soluble of 5mL It is stirred 3 minutes in liquid, and sodium hydroxide solution is added and adjusts pH to 8;(2) by two (the imidazoles first of 4- amino -3,5- of 0.05mmol Base) -1,2,4- triazoles (3-abit) are added in the methanol solution of 5mL, are stirred 7 minutes;It (3) will be obtained in step (1) Solution is placed in the CH that 3mL in reaction tube and is added3OH and H2O buffer solvent, the wherein CH of buffer solvent3OH and H2The volume ratio of O For 1:0.5, then solution obtained in step (2) is added in reaction tube, crystallized, is filtered, washed after sealing, drying to obtain Luminescent crystal material [Zn (OBA) (3-abit)] n;
2、Fe3+The test of ion selectivity detection performance: it is 3 that the luminescent crystal material (1 milligram) of preparation, which is added to volume, In milliliter, the metal cation aqueous solution that solubility is 0.01 mol/L, then ultrasonic two hours obtained stable suspensions exist The fluorescence spectrum of different cationic aqueous solutions is measured under 350nm exciting light.
3, X-ray diffraction is analyzed: luminescent crystal material (5mg) powder of preparation being put into X-ray diffractometer and is spread out Penetrate Interferogram Analysis.
Embodiment 6:
1, the preparation of luminescent crystal material: the following steps are included:
(1) the 4,4 '-oxydibenzoic acids (OBA) of the zinc nitrate of 0.1mmol and 0.05mmol are added to the water-soluble of 5mL It is stirred 5 minutes in liquid, and sodium hydroxide solution is added and adjusts pH to 8;(2) by two (the imidazoles first of 4- amino -3,5- of 0.05mmol Base) -1,2,4- triazoles (3-abit) are added in the methanol solution of 5mL, are stirred 5 minutes;It (3) will be obtained in step (1) Solution is placed in the CH that 3mL in reaction tube and is added3OH and H2O buffer solvent, the wherein CH of buffer solvent3OH and H2The volume ratio of O For 1:0.5, then solution obtained in step (2) is added in reaction tube, crystallized, is filtered, washed after sealing, drying to obtain Luminescent crystal material [Zn (OBA) (3-abit)] n;
2、Fe3+The test of ion selectivity detection performance: it is 3 that the luminescent crystal material (1 milligram) of preparation, which is added to volume, In milliliter, the metal cation aqueous solution that solubility is 0.01 mol/L, then ultrasonic two hours obtained stable suspensions exist The fluorescence spectrum of different cationic aqueous solutions is measured under 350nm exciting light.
3, X-ray diffraction is analyzed: luminescent crystal material (5mg) powder of preparation being put into X-ray diffractometer and is spread out Penetrate Interferogram Analysis.
Above embodiment is used for illustrative purposes only, and is not limitation of the present invention, related technical field Those of ordinary skill without departing from the spirit and scope of the present invention can be with various changes can be made and modification, therefore institute There is equivalent technical solution also to should belong to scope of the invention.

Claims (4)

1. one kind has selectivity detection Fe3+The luminescent crystal material of ion, it is characterised in that: the change of the luminescent crystal material Formula is [Zn (OBA) (3-abit)]n, wherein OBA is 4,4 '-oxydibenzoic acids, and the luminescent crystal material is to be connected by four The one-dimensional trapezoidal skeleton structure of one kind made of the Zn connect and two kinds of bridge ligands OBA and 3-abit are constructed, belongs to anorthic system, empty Between group be P-1, cell parameter is α=73.382 (2) °, β=76.088 (2) °, γ=80.229 (2) °, Z=2.
2. a kind of described in claim 1 with selectivity detection Fe3+The preparation method of the luminescent crystal material of ion, including with Lower step:
(1) by zinc nitrate and 4,4 '-oxydibenzoic acids are added in aqueous solution, and are stirred 3-6 minutes, and alkaline solution tune is added Save pH to 6-8;
(2) 4- amino -3,5- two (imidazolmethyl) -1,2,4- triazole is added in methanol solution and is stirred 5-7 minutes;
(3) solution obtained in step (1) is placed in reaction tube, and buffer solvent is added, be slowly added to obtain in step (2) Solution, crystallized, be filtered, washed after sealing, drying to obtain luminescent crystal material [Zn (OBA) (3-abit)]n
3. according to claim 2 have selectivity detection Fe3+The preparation method of the luminescent crystal material of ion, feature Be zinc nitrate, 4,4 '-oxydibenzoic acids, 4- amino -3,5- two (imidazolmethyl) -1,2,4- triazole molar ratio be 1: 0.5~1:0.5~1.
4. according to claim 2 there is selectivity detection to detect Fe3+The preparation method of the luminescent crystal material of ion, It is characterized in that, the buffer solvent is the mixed solution of CH3OH and H2O, and wherein the volume ratio of CH3OH and H2O is 1:0.5~1.
CN201710543173.1A 2017-07-05 2017-07-05 One kind having selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof Active CN107384373B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710543173.1A CN107384373B (en) 2017-07-05 2017-07-05 One kind having selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710543173.1A CN107384373B (en) 2017-07-05 2017-07-05 One kind having selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof

Publications (2)

Publication Number Publication Date
CN107384373A CN107384373A (en) 2017-11-24
CN107384373B true CN107384373B (en) 2019-10-11

Family

ID=60335229

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710543173.1A Active CN107384373B (en) 2017-07-05 2017-07-05 One kind having selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof

Country Status (1)

Country Link
CN (1) CN107384373B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108034990B (en) * 2017-12-08 2019-08-06 江南大学 Can it is highly sensitive detection 2,4,6- trinitrophenol luminescent crystal material preparation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106866989B (en) * 2017-01-20 2019-08-16 江南大学 One kind having selectivity detection Fe3+The preparation method of the luminescent crystal material of ion

Also Published As

Publication number Publication date
CN107384373A (en) 2017-11-24

Similar Documents

Publication Publication Date Title
CN110655529B (en) Preparation of luminescent crystal material for rapidly and highly sensitively detecting high manganese acid radical ions
CN101435778B (en) Method for qualitatively detecting CU<2+> in solution directly by eye
CN109134880A (en) A kind of Eu (III)-metal organic framework and the preparation method and application thereof
CN110128674B (en) Water-stable rare earth metal organic framework material for fluorescence detection of sulfonamide antibiotics and preparation method thereof
CN106084247B (en) A kind of rare earth metal europio organic crystalline material, prepares and its applies
Kanan et al. Recent advances in nanocomposite luminescent metal-organic framework sensors for detecting metal ions
CN106866989B (en) One kind having selectivity detection Fe3+The preparation method of the luminescent crystal material of ion
CN108794759B (en) Zinc-based luminescent metal organic framework material and preparation method and application thereof
CN111500282B (en) Uranyl ion fluorescent probe based on target terbium-organic framework poly tungstate and preparation method and application thereof
CN107589162A (en) A kind of preparation method and application based on complex of iridium Photoelectrochemistrbiosensor biosensor
CN110240707B (en) Post-modified metal-organic framework material for detecting iron ions and preparation method and application thereof
CN107384373B (en) One kind having selectivity detection Fe3+Luminescent crystal material of ion and preparation method thereof
CN102391150A (en) Iron-ion fluorescent probe compound and preparation method thereof
Song et al. A luminescent sensor based on a Cd2+ complex for the detection of nitrofuran antibiotics in aqueous solution
CN100579982C (en) Molecular compound of fluorescence chemical sensor of nitrogen hetero-cycles functionalized 1,3-diketone europium complexes, preparation method and application
CN108997433B (en) Manganese-based luminescent metal organic framework material and preparation method and application thereof
CN113278157B (en) Cadmium coordination polymer and preparation method and application thereof
KR20130126400A (en) Squarylium dye and method for detecting anion
CN113717392A (en) Two-dimensional Cu-MOF fluorescent probe material and preparation method and application thereof
CN106496253A (en) A kind of multi-functional zinc/cadmium complex of thiophene phenyl organic ligand and its application
CN109283163B (en) Method for detecting L-cysteine based on calcium-metal organic framework material as fluorescent probe
CN109265473B (en) Zinc (II) metal organic complex containing mixed ligand and preparation method and application thereof
CN110776523B (en) Ultra-stable three-dimensional luminous zinc (II) metal organic framework material and preparation method and application thereof
CN114920762B (en) Organic hybridization cuprous iodide dual-response fluorescent probe material and preparation method thereof
CN109467712A (en) A kind of metal organic framework MOF-Zn fluorescent sensor material and its preparation method and application

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant