NL2030557B1 - Europium—based metal-organic framework material for fluorescence recognition of antibiotics and preparation method thereof - Google Patents

Europium—based metal-organic framework material for fluorescence recognition of antibiotics and preparation method thereof Download PDF

Info

Publication number
NL2030557B1
NL2030557B1 NL2030557A NL2030557A NL2030557B1 NL 2030557 B1 NL2030557 B1 NL 2030557B1 NL 2030557 A NL2030557 A NL 2030557A NL 2030557 A NL2030557 A NL 2030557A NL 2030557 B1 NL2030557 B1 NL 2030557B1
Authority
NL
Netherlands
Prior art keywords
europium
organic framework
framework material
antibiotics
based metal
Prior art date
Application number
NL2030557A
Other languages
Dutch (nl)
Other versions
NL2030557A (en
Inventor
Li Ling
Zhang Li
You Shengyong
Zou Jiyong
Original Assignee
Inst Applied Chemistry Jiangxi Academy Sciences
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 Inst Applied Chemistry Jiangxi Academy Sciences filed Critical Inst Applied Chemistry Jiangxi Academy Sciences
Priority to NL2030557A priority Critical patent/NL2030557B1/en
Publication of NL2030557A publication Critical patent/NL2030557A/en
Application granted granted Critical
Publication of NL2030557B1 publication Critical patent/NL2030557B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/001—Macromolecular compounds containing organic and inorganic sequences, e.g. organic polymers grafted onto silica
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)

Abstract

The present disclosure provides a europium-based metal-organic framework material for fluorescence recognition of antibiotics and a preparation method of the europium-based metal-organic framework material. 2,5-furandicarboxylic acid is used as a ligand, rare earth europium ions are used as a metal center, and the europium-based metal-organic framework material is synthesized through a solvothermal method. The material prepared by the present disclosure is simple in preparation method, high in purity and good in activity, can be used for detection after being aired at a room temperature, does not need to be pretreated, is easy to implement, is rapid, simple, convenient, good in selectivity, high in sensitivity, low in detection limit, and recyclable in detection of the antibiotics, and thus has huge potential application value in preparation of fluorescence probe solid-state devices and detection of the antibiotics.

Description

EUROPIUM-BASED METAL-ORGANIC FRAMEWORK MATERIAL FOR FLUORESCENCE RECOGNITION OF ANTIBIOTICS AND PREPARATION METHOD THEREOF TECHNICAL FIELD
[01] The present disclosure relates to a europium-based metal-organic framework material for fluorescence recognition of antibiotics and a preparation method of the europium-based metal-organic framework material, and belongs to the technical field of porous molecular crystal materials.
BACKGROUND ART
[02] Metal-organic framework fluorescence sensing materials are considered to be one of the most promising detection methods, and are widely used to identify harmful substances such as anions, cations, and small molecular organics. See H.-C. Zhou et al, Chem. Soc. Rev, 2014, 43, 5415-5418 and S.-K. Ghosh et al., Chem. Soc. Rev, 2017, 46, 3242-3285. In this method, a fluorescence intensity changes with an analyte concentration, such that the presence of the analyte can be detected. Compared with traditional analysis technology, fluorescence sensing detection based on metal-organic framework has the characteristics of high precision, high sensitivity, small size, short response time, and good adaptability. In recent years, there have been many reports on the fluorescence response of a single antibiotic by the use of metal-organic frameworks. For example, Zhou et al. reported a metal-organic framework material of terbium and zinc. The results of fluorescence sensing detection show that: the material has good detection performance for nitrofuran drugs such as nifurazolidone (FZD), nitrofurazone (NFZ), and nitrofurantoin (NFT) in water (see: Z.-H. Zhou et al., Inorg. Chem. 2018, 57, 3833). Han et al. reported a metal-organic framework material of sodium and europium. The results of fluorescence sensing detection show that: the material has a good selective detection ability for ornidazole (OND) in water (see: M.-L. Han et al., J. Mater. Chem. C, 2017, 5, 8469).
[03] Chinese patent CN110128674 discloses a water-stable rare earth metal-organic framework material for fluorescence detection of sulfonamide antibiotics and a preparation method of the rare earth metal-organic framework material. However, there are still few studies on the simultaneous fluorescence response of multiple antibiotics,
especially the simultaneous fluorescence response of the rare earth metal-organic framework to multiple antibiotics has not been reported.
SUMMARY
[04] An objective of the present disclosure is to solve the above problems and obtain a europium-based metal-organic framework material with chemical stability and simultaneous fluorescence response to nitrofuran antibiotics, nitroimidazole antibiotics, and sulfonamide antibiotics. The present disclosure provides a europium-based metal- organic framework material for fluorescence recognition of antibiotics and a preparation method of the europium-based metal-organic framework material.
[05] A technical solution of the present disclosure is as follows: A europium-based metal-organic framework material for fluorescence recognition of antibiotics, having a chemical formula: {[Eu2(FDA):(H20);(DMF)-DMF-2H:0]},, where in the formula, n is a natural number from 1 to positive infinity; FDA? is obtained by deprotonation of 2 5-furandicarboxylic acid; and DMF is N,N-dimethylformamide.
[06] A preparation method of a europium-based metal-organic framework material for fluorescence recognition of antibiotics includes the following steps:
[07] (1) dissolving organic ligands H2FDA in a N,N-dimethylformamide solvent respectively;
[08] (2) dissolving Mn(OAc)2-4H20 and Eu(NO: );-6H20 in water;
[09] (3) mixing two solutions obtained in steps (1) and (2), then putting a mixed solution in a closed hydrothermal reactor for a reaction at a constant temperature of 90°C for 72 h, taking out a product, and then separating a solid; and
[10] (4) washing the solid with N,N-dimethylformamide for many times to obtain a colorless bulk crystal.
[11] The beneficial effect of the present disclosure is that is the europium-based metal-organic framework material of the present disclosure is different from an existing europium-based framework material and is a new material. The fluorescence change curve of the europium-based metal-organic framework material of the present disclosure in the DMF solution with the low concentration has a linear relationship with the concentration of the antibiotics. Different from the prior art, the test conditions are all aqueous solutions, and the prior art can only recognize the sulfonamide antibiotics by fluorescence alone. The present disclosure can effectively recognize the three types of antibiotics at the same time, and the detection limit is much lower than the prior art.
[12] The material prepared by the present disclosure is simple in preparation method, high in purity and good in activity, can be used for detection after being aired at a room temperature, does not need to be pretreated, is easy to implement, is rapid, simple, convenient, good in selectivity, high in sensitivity, low in detection limit, and recyclable in detection of the antibiotics, and thus has huge potential application value in preparation of fluorescence probe solid-state devices and detection of the antibiotics.
BRIEF DESCRIPTION OF THE DRAWINGS
[13] FIG. 1 is a three-dimensional structure diagram of a europium-based metal- organic framework material of the present disclosure;
[14] FIG. 2 is a fluorescence spectrum of the europium-based metal-organic framework material of the present disclosure in different solvents;
[15] FIG. 3 is a fluorescence spectrum of the europium-based metal-organic framework material in FZD solutions with different concentrations in an example of the present disclosure;
[16] FIG. 4 is a graph of the concentration of FZD in the present disclosure versus a fluorescence intensity Io/I of a rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the FZD versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example ([FZD]<16 pmol/L);
[17] FIG. 5 is a fluorescence spectrum of the europium-based metal-organic framework material in NFT solutions with different concentrations in the example of the present disclosure;
[18] FIG. 61s a graph of the concentration of NFT in the present disclosure versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the NFT versus the fluorescence intensity Io/I of the rare earth metal-organic framework material in the example ([NFT]<16 pmol/L);
[19] FIG. 7 is a fluorescence spectrum of the europium-based metal-organic framework material in NFZ solutions with different concentrations in the example of the present disclosure;
[20] FIG. 8 is a graph of the concentration of NFZ in the present disclosure versus the fluorescence intensity Io/I of the rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the NFZ versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example ([NFZ]<16 pmol/L); J21] FIG. 9 is a fluorescence spectrum of the europium-based metal-organic framework material in MND solutions with different concentrations in the example of the present disclosure,
[22] FIG. 10 is a graph of the concentration of MND in the present disclosure versus the fluorescence intensity Io/I of the rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the MND versus the fluorescence intensity Io/I of the rare earth metal-organic framework material in the example ([MND]<16 pmol/L);
[23] FIG. 11 is a fluorescence spectrum of the europium-based metal-organic framework material in RND solutions with different concentrations in the example of the present disclosure;
[24] FIG. 12 is a graph of the concentration of RND in the present disclosure versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the RND versus the fluorescence intensity Io/I of the rare earth metal-organic framework material in the example ([RND]<16 umol/L);
[25] FIG. 13 is a fluorescence spectrum of the europium-based metal-organic framework material in DND solutions with different concentrations in the example of the present disclosure;
[26] FIG. 14 is a graph of the concentration of DND in the present disclosure versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the DND versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example ([DND]<16 umol/L);
[27] FIG. 15 1s a fluorescence spectrum of the europium-based metal-organic framework material in OND solutions with different concentrations in the example of the present disclosure;
[28] FIG. 16 is a graph of the concentration of OND in the present disclosure versus the fluorescence intensity Io/I of the rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the OND versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example ([OND]<16 pmol/L);
[29] FIG. 17 is a fluorescence spectrum of the europium-based metal-organic 5 framework material in SDZ solutions with different concentrations in the example of the present disclosure;
[30] FIG. 18 is a graph of the concentration of SDZ in the present disclosure versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the SDZ versus the fluorescence intensity Io/I of the rare earth metal-organic framework material in the example ([SDZ]<16 pmol/L);
[31] FIG. 19 is a fluorescence spectrum of the europium-based metal-organic framework material in SMZ solutions with different concentrations in the example of the present disclosure; and
[32] FIG. 20 is a graph of the concentration of SMD in the present disclosure versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the SMD versus the fluorescence intensity lo/I of the rare earth metal-organic framework material in the example ([SMD]<16 pmol/L).
DETAILED DESCRIPTION OF THE EMBODIMENTS
[33] Inthe present example, a europium-based metal-organic framework material for fluorescence recognition of antibiotics has a chemical formula: {[Euz(FDA )3(H20)3(DMF)- DMF -2H,01} n.
[34] In the formula, n is a natural number from 1 to positive infinity. FDA? is obtained by deprotonation of 2 5-furandicarboxylic acid. DMF is N,N- dimethylformamide.
[35] The europium-based metal-organic framework material belongs to a monoclinic system, a space group is P2i/n, and unit cell parameters are: a=10.3176(3) A, b=21.0431(7) A, c=15.6348(4) A, 0=90°, B=93.844(3)°, and y=90°.
[36] In a basic structural unit of the europium-based metal-organic framework material, there are two europium ions in coordination environments, 3 deprotonated ligands FDA? 3 coordinated water molecules, 1 coordinated DMF molecule, 1 free
DMF molecule, and 2 free water molecules. Europium ions adopt a { EuOs} coordination mode of a deformed single-cap tetragonal anti-prism, and Eul ions are coordinated with 8 oxygen atoms from 6 dehydrogenation ligands FDA? and 1 oxygen atom from water respectively. Eu2 ions are coordinated with 6 oxygen atoms from 4 dehydrogenation ligands FDA?%, 2 oxygen atoms in water, and 1 DMF respectively. The adjacent europium ions form a three-dimensional network structure in space through the dehydrogenation ligands FDA?"
[37] The europium-based metal-organic framework material is simplified into a 6, 6- connected single-node pcu topology with a point symbol of {412.63}.
[38] Inthe present example, a preparation method of a europium-based metal-organic framework material for fluorescence recognition of antibiotics includes the following steps for synthesis.
[39] (1) 31.2 mg of organic ligands H:FDA are dissolved in 3 mL of a N,N- dimethylformamide solvent respectively.
[40] (2) 24.5 mg of Mn(OAc)}: 4H:0 and 44.6 mg of Eu(NO: )3:6H:0 are dissolved in water.
[41] (3) Two solutions obtained in steps (1) and (2) are mixed. Then a mixed solution is put in a closed hydrothermal reactor for a reaction at a constant temperature of 90°C for 72 h. A product is taken out. A solid is separated.
[42] (4) The solid is washed with N,N-dimethylformamide and water for three times to obtain a colorless bulk crystal. A yield calculated based on the metal europium is 65%.
[43] The properties of the europium-based metal-organic framework material for fluorescence recognition of antibiotics prepared in the present example are characterized as follows.
[44] (1) Structure determination of the europium-based metal-organic framework material for fluorescence recognition of antibiotics in the present example:
[45] A crystal structure is determined using a Supernova X-ray single crystal diffractometer. Graphite-monochromatized Mo-Ko rays (2=0.71073 A) are used as an incident radiation source. Diffraction points are collected in an w-¢ scanning mode. Unit cell parameters are obtained through correction by the least square method. The crystal structure is solved by the SHELXL-97 direct method from the difference Fourier electron density map, and the crystal structure is corrected by Lorentz and polarization effects. All H atoms are synthesized by difference Fourier and determined by calculation of ideal positions. The exact number of solvent molecules is determined by thermogravimetric and elemental analysis tests. Detailed crystal determination data are shown in Table I.
[46] Table 1 Crystallographic data of europium-based metal-organic framework material Unit cell parameter 2=10.3176(3) A, b=21.0431(7) A, c=15.6348(4) A, en Density 1.966 oe |
[47] FIG. 1 is a three-dimensional structure diagram of a europium-based metal- organic framework material in the present example. In a formula, n is a natural number from 1 to positive infinity, indicating that the material is a polymer.
[48] (2) Fluorescence characterization of europium-based metal-organic framework material in the present example:
[49] FIG. 2 is a fluorescence spectrum of the europium-based metal-organic framework material in different solvents in the example of the present disclosure.
[S0] FIG. 3 is a fluorescence spectrum of the europium-based metal-organic framework material in FZD solutions with different concentrations in the example of the present disclosure. FIG. 4 is a graph of the concentration of the FZD in the present disclosure versus a fluorescence intensity Io/I of the europium-based metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the FZD versus the fluorescence intensity Io/I of the europium-based metal-organic framework material in the example ([FZD]<16 pmol/L). [S1] FIG. 5 is a fluorescence spectrum of the europium-based metal-organic framework material in NFT solutions with different concentrations in the example of the present disclosure. FIG. 6 is a graph of the concentration of the NFT in the present disclosure versus the fluorescence intensity IoT of the europium-based metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the NFT versus the fluorescence intensity Io’I of the europium-based metal-organic framework material in the example ([NFT]<16 pmol/L).
[52] FIG. 7 is a fluorescence spectrum of the europium-based metal-organic framework material in NFZ solutions with different concentrations in the example of the present disclosure. FIG. 8 is a graph of the concentration of the NFZ in the present disclosure versus the fluorescence intensity Io/I of the europium-based metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the NFZ versus the fluorescence intensity Io/I of the europium-based metal-organic framework material in the example ([NFZ]<16 pmol/L). [S3] FIG. 9 is a fluorescence spectrum of the europium-based metal-organic framework material in MND solutions with different concentrations in the example of the present disclosure.
[54] FIG. 10 is a graph of the concentration of the MND in the present disclosure versus the fluorescence intensity Io/I of the europium-based metal-organic framework material in the example, where an inset is an Stern-Volmer linear graph of the concentration of the MND versus the fluorescence intensity Io/I of the europium-based metal-organic framework material in the example ((MND]<16 pmol/L). It can be seen from the figure that when the concentration of the MND is low (0-16 pmol/L), the fluorescence intensity lo/I of the europium-based metal-organic framework material has a linear relationship with the concentration of the MND, and its detection limit is 0.346 umol-L-!. When the concentration of the MND is high, the fluorescence intensity Io/I of the europium-based metal-organic framework material increases slowly at first and then quickly with the concentration of the MND, and no longer has a linear relationship with the concentration of the MND.

Claims (2)

-9- Conclusies-9- Conclusions 1. Europium-gebaseerd organometallisch roostermateriaal voor fluorescentieherkenning van antibiotica, dat een scheikundige formule: {[Eua(FDA):(H20)3(DMF)-DMF-2H,0] }4 heeft, waarbij in de formule, n een natuurlijk getal van 1 tot positief oneindig is; FDA? is verkregen door deprotonatie van 2,5-furaandicarbonzuur; en DMF N‚N- dimethylformamide is; het Europium-gebaseerde organometallische roostermateriaal behoort tot een monoklien stelsel, een ruimtegroep P21 is, en eenheidscelparameters als volgt zijn: a=10.3176(3) A, b=21.0431(7) A, c=15.6348(4) A, 0=90°, B=93.844(3)°, en y=90°; en in een structurele basiseenheid van het Europium-gebaseerde organometallische roostermateriaal, er twee Europium-ionen in coördinatieomgevingen, 3 gedeprotoneerde liganden FDA, 3 gecoördineerde watermoleculen, 1 gecoördineerd DMF-molecuul, 1 vrij DMF-molecuul, en 2 vrije watermoleculen zijn; waarbij de Europium-ionen een {EuOo} coördinatiemodus van een vervormd enkel-kaps tetragonaal antiprisma aannemen, en Eul-ionen zijn gecoördineerd met respectievelijk 8 zuurstofatomen van 6 dehydrogenatieliganden FDA? en 1 zuurstofatoom van water; Eu2-ionen zijn gecoördineerd met respectievelijk 6 zuurstofatomen van 4 dehydrogenatieliganden FDA? 2 zuurstofatomen in water, en 1 DMF; en de naastgelegen Europium-ionen in de ruimte een driedimensionale netwerkstructuur vormen.A Europium-based organometallic lattice material for fluorescence recognition of antibiotics, which has a chemical formula: {[Eua(FDA):(H2O)3(DMF)-DMF-2H,0] }4, where in the formula, n is a natural number from 1 to positive infinity; FDA? is obtained by deprotonation of 2,5-furandicarboxylic acid; and DMF is N,N-dimethylformamide; the Europium-based organometallic lattice material belongs to a monoclinic system, is a space group P21, and unit cell parameters are as follows: a=10.3176(3) A, b=21.0431(7) A, c=15.6348(4) A, 0=90 °, B=93.844(3)°, and y=90°; and in a basic structural unit of the Europium-based organometallic lattice material, there are two Europium ions in coordination environments, 3 deprotonated FDA ligands, 3 coordinated water molecules, 1 coordinated DMF molecule, 1 free DMF molecule, and 2 free water molecules; where the Europium ions adopt a {EuOo} coordination mode of a distorted single-cap tetragonal antiprism, and Eul ions are coordinated to 8 oxygen atoms of 6 dehydrogenation ligands, respectively FDA? and 1 oxygen atom of water; Eu2 ions are coordinated to 6 oxygen atoms of 4 dehydrogenation ligands respectively FDA? 2 oxygen atoms in water, and 1 DMF; and the adjacent Europium ions in space form a three-dimensional network structure. 2. Werkwijze voor bereiding van een Europium-gebaseerd organometallisch roostermateriaal voor fluorescentieherkenning van antibiotica, die de volgende stappen omvat: (1) het oplossen van organische liganden H>FDA in een N,N- dimethylformamide-oplosmiddel respectievelijk; (2) het oplossen van Mn(OAc):-4H:0 en Eu(NO:)3:6H20 in water; (3) het mengen van de twee oplossingen die in stappen (1) en (2) zijn verkregen, daarna het plaatsen van een gemengde oplossing in een gesloten hydrothermische reactor voor een reactie bij een constante temperatuur van 90°C voor 72 uur, het uitnemen van een product, en vervolgens het afscheiden van een vaste stof, en (4) het vele malen spoelen van de vaste stof met N,N-dimethylformamideA method for preparing a Europium-based organometallic lattice material for fluorescence recognition of antibiotics, comprising the steps of: (1) dissolving organic ligands H>FDA in an N,N-dimethylformamide solvent, respectively; (2) dissolving Mn(OAc):-4H:0 and Eu(NO:)3:6H20 in water; (3) mixing the two solutions obtained in steps (1) and (2), then placing a mixed solution in a closed hydrothermal reactor for reaction at a constant temperature of 90°C for 72 hours, extracting a product, then separating a solid, and (4) rinsing the solid many times with N,N-dimethylformamide - 10 - teneinde een kleurloos bulkkristal, het Europium-gebaseerde organometallische roostermateriaal voor fluorescentieherkenning van de antibiotica, te verkrijgen.- 10 - in order to obtain a colorless bulk crystal, the Europium-based organometallic lattice material for fluorescence recognition of the antibiotics.
NL2030557A 2022-01-14 2022-01-14 Europium—based metal-organic framework material for fluorescence recognition of antibiotics and preparation method thereof NL2030557B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NL2030557A NL2030557B1 (en) 2022-01-14 2022-01-14 Europium—based metal-organic framework material for fluorescence recognition of antibiotics and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL2030557A NL2030557B1 (en) 2022-01-14 2022-01-14 Europium—based metal-organic framework material for fluorescence recognition of antibiotics and preparation method thereof

Publications (2)

Publication Number Publication Date
NL2030557A NL2030557A (en) 2022-11-15
NL2030557B1 true NL2030557B1 (en) 2022-11-30

Family

ID=84046036

Family Applications (1)

Application Number Title Priority Date Filing Date
NL2030557A NL2030557B1 (en) 2022-01-14 2022-01-14 Europium—based metal-organic framework material for fluorescence recognition of antibiotics and preparation method thereof

Country Status (1)

Country Link
NL (1) NL2030557B1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117065730A (en) * 2023-08-03 2023-11-17 中国电建集团重庆工程有限公司 New material for removing or detecting tetracycline in liquid and detection system thereof

Also Published As

Publication number Publication date
NL2030557A (en) 2022-11-15

Similar Documents

Publication Publication Date Title
Eppley et al. High-Spin Molecules: Unusual magnetic susceptibility relaxation effects in [Mn12O12 (O2CEt) 16 (H2O) 3](S= 9) and the one-electron reduction product (PPh4)[Mn12O12 (O2CEt) 16 (H2O) 4](S= 19/2)
CN108998007B (en) Preparation method of rare earth metal organic framework material
CN113234233B (en) Europium-based metal-organic framework material with antibiotic fluorescence recognition function and preparation method thereof
CN103242352B (en) A kind of luminescent metal organic framework materials with chemical sensitisation function and its preparation method and application
CN105985362B (en) A kind of method for preparing zeolite imidazole ester frame structure material
CN110128674B (en) Water-stable rare earth metal organic framework material for fluorescence detection of sulfonamide antibiotics and preparation method thereof
Su et al. A monomeric bowl-like pyrogallol [4] arene Ti 12 coordination complex
CN109776504A (en) A kind of metal-organic framework material and preparation method and applications based on low symmetrical pyrazoles-Carboxylic acid ligand Zn
CN107556305B (en) Fluorescent probe for detecting aluminum ions, preparation method and application
NL2030557B1 (en) Europium—based metal-organic framework material for fluorescence recognition of antibiotics and preparation method thereof
Wang et al. Tb (iii) postsynthetic functional coordination polymer coatings on ZnO micronanoarrays and their application in small molecule sensing
CN108558917B (en) Zinc-furandicarboxylic acid organic framework material and preparation method thereof
CN107987282B (en) Water-stable lanthanide metal-organic framework material, preparation and application thereof
Karipides et al. Stereochemistry of carboxylate complexes. Crystal structure of (-) 598-malatodiaquomanganese (II) hydrate
CN101735798A (en) Rare earth organic framework material having sensing function to acetone, preparation method and application thereof
CN108384027B (en) Zinc-organic framework with acetylacetone fluorescent response and preparation method thereof
CN114133581B (en) Mg-MOFs, preparation method thereof and application thereof in iron ion detection
Yu et al. Structure, assembly mechanism and magnetic properties of heterometallic dodecanuclear nanoclusters Dy III4 M II8 (M= Ni, Co)
CN108048075B (en) Calcium ion fluorescent probe based on aggregation induction effect and preparation method and application thereof
CN108424527B (en) Synthetic method of Zn (II) complex of three-dimensional mixed ligand and application of fluorescent probe
CN114507353B (en) Preparation method and application of organic hybrid perovskite/metal organic framework material
CN108559097A (en) 3,3 &#39;, 5,5 &#39;-azoxy benzene tetracarboxylic acid europiums（III）Metal coordinating polymer and its synthetic method and application
CN112940279B (en) Layered column type zinc-based metal-organic framework material and preparation method thereof
CN108822051A (en) The synthetic method and application of Zn (II) complex of fluorescent type three-dimensional
CN114778636A (en) Preparation method of composite electrode for simultaneously measuring hydroquinone and catechol