WO2020218871A1 - Corps magnétique à nanoagrégats d'argent dopé avec un atome de métal different, et son procédé de préparation - Google Patents

Corps magnétique à nanoagrégats d'argent dopé avec un atome de métal different, et son procédé de préparation Download PDF

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WO2020218871A1
WO2020218871A1 PCT/KR2020/005428 KR2020005428W WO2020218871A1 WO 2020218871 A1 WO2020218871 A1 WO 2020218871A1 KR 2020005428 W KR2020005428 W KR 2020005428W WO 2020218871 A1 WO2020218871 A1 WO 2020218871A1
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dissimilar metal
silver
doped
group
formula
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PCT/KR2020/005428
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Korean (ko)
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이동일
김민석
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연세대학교 산학협력단
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
    • B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
    • B22F1/16—Metallic particles coated with a non-metal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
    • B22F9/00—Making metallic powder or suspensions thereof
    • B22F9/16—Making metallic powder or suspensions thereof using chemical processes
    • B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
    • B22F9/24—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds starting from liquid metal compounds, e.g. solutions
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
    • H01F1/00—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties

Definitions

  • the present invention relates to a silver nanocluster magnetic material doped with dissimilar metal atoms and a method of manufacturing the same.
  • a nanocluster or superatom composed of a certain number of metal atoms and ligands follows the macroatomic orbital theory, in which the valence electrons of the particles are newly defined, and this is considered to be one giant atom. It is a theory.
  • Nanoclusters are stable compared to one atom or nanoparticles, and have strong molecular properties than metallic properties, and thus have optical and electrochemical properties that are completely different from nanoparticles.
  • optical, electrical and catalytic properties of nanoclusters are sensitively changed depending on the number of metal atoms, types of metal atoms, and ligands, research on nanoclusters is actively in progress in a wide variety of fields.
  • magnetic nanoparticles have a very diverse range of applications, and interest in magnetic nanoparticles is further amplified as various application fields using magnetism are developed, especially in the biomedical industry.
  • Such applications include magnetic resonance imaging (MRI) contrast agents, material separation using magnetism, drug delivery using magnetism, material sensor using magnetism, and high-frequency magnetic field heat treatment.
  • MRI magnetic resonance imaging
  • magnetic nanoparticles have a disadvantage in that the size and shape of the particles are non-uniform, and it is difficult to control the surface properties equally, so that the form of spin clustering is not clear and non-uniform.
  • nanocluster magnetic material has a very clear spin shape due to its completely uniform size and structure, and has excellent dispersibility in solution, so it can be used in various applications using magnetism. It can be possible.
  • the nanocluster magnetic material has a disadvantage in that magnets are smaller than that of magnetic nanoparticles, there is a need to develop a nanocluster magnetic material having a greater magnetic property.
  • Korean Patent Publication No. 10-1178512 is proposed as a prior document similar to this.
  • an object of the present invention is to provide a silver nanocluster magnetic material doped with dissimilar metal atoms, which has excellent magnetic properties, has a completely uniform size and structure, and has a very clear spin shape, and a method of manufacturing the same.
  • One aspect of the present invention relates to a silver nanocluster magnetic material doped with a dissimilar metal atom satisfying the following Formula 1.
  • SR is an organothiol-based ligand
  • M is ruthenium (Ru) or rhodium (Rh).
  • the organothiol-based ligand in Formula 1 may be an arylthiol having 6 to 30 carbon atoms in which C1-C10 alkyl is substituted.
  • another aspect of the present invention is a) preparing a reaction solution by reacting a silver precursor and an organic thiol-based ligand compound; And b) adding a dissimilar metal precursor, a reaction catalyst, and a reducing agent to the reaction solution to prepare a nanocluster magnetic material that satisfies the following formula (1); including, a method for producing a silver nanocluster magnetic material doped with a dissimilar metal atom. will be.
  • SR is an organothiol-based ligand
  • M is ruthenium (Ru) or rhodium (Rh).
  • the molar ratio of the silver precursor: the dissimilar metal precursor may be 50: 0.8 to 1.2.
  • the silver precursor according to an embodiment of the present invention may be any one or two or more selected from the group consisting of AgNO 3 , AgBF 4 , AgCF 3 SO 3 , AgClO 4 , AgO 2 CCH 3 and AgPF 6 .
  • the magnetic material of the silver nanocluster doped with dissimilar metal atoms according to the present invention may maintain the intrinsic characteristics of the doped atom as it is by doping one ruthenium atom or rhodium atom into the silver nanocluster, and thus may have excellent magnetic properties.
  • the size and structure may be completely uniform, and accordingly, the spin shape may be very clear.
  • MRI magnetic resonance imaging
  • RhAg 24 SPhMe 2 18 .
  • RhAg 24 (SPhMe 2 ) 18 is a 1 H NMR analysis result of RhAg 24 (SPhMe 2 ) 18 .
  • UV-Vis ultraviolet-visible light
  • first, second, A, B, (a) and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term.
  • Existing magnetic nanoparticles have very good magnetic properties, but the size and shape of the particles are non-uniform, and it is difficult to control the same surface properties, and thus, there is a disadvantage in that the spin dense form is not clear and non-uniform.
  • nanocluster magnetic bodies unlike magnetic nanoparticles of non-uniform size and shape, nanocluster magnetic bodies have a very clear spin shape as they are completely uniform in size and structure, but have a disadvantage in that magnets are smaller than magnetic nanoparticles.
  • the present inventors showed that the nanoclusters in which 24 silver atoms and 1 dissimilar metal atom are bonded in a specific structure have the same configuration, so that the size and structure are completely uniform, and the intrinsic characteristics of the doped atoms
  • the present invention was completed by discovering that it can be maintained as it is and has excellent magnetic properties.
  • one aspect of the present invention relates to a silver nanocluster magnetic material doped with a dissimilar metal atom satisfying the following Formula 1.
  • SR is an organothiol-based ligand
  • M is ruthenium (Ru) or rhodium (Rh).
  • the magnetic material of the silver nanocluster doped with dissimilar metal atoms according to the present invention is doped with one ruthenium atom or rhodium atom in the silver nanocluster, so that the intrinsic characteristics of the doped atom can be maintained as it is, and thus can have excellent magnetic properties. .
  • the size and structure may be completely uniform, and accordingly, the spin shape may be very clear.
  • MRI magnetic resonance imaging
  • the organic thiol-based ligand SR is a C1-C30 alkanthiol, a C6-C30 arylthiol, a C3-C30 cycloalcanthiol, a C5-C30 hetero It may be any one or two or more selected from the group consisting of arylthiol, heterocycloalkanethiol having 3 to 30 carbon atoms, and arylalkanethiol having 6 to 30 carbon atoms, and the organothiol-based ligand is one or more hydrogens in the functional group as a substituent.
  • the substituent is an alkyl group having 1 to 10 carbon atoms, a halogen group (-F, -Br, -Cl, -I), a nitro group, a cyano group, a hydroxy group, an amino group, and 6 to 20 carbon atoms.
  • an aryl group an alkenyl group having 2 to 7 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, or a heteroaryl group having 4 to 20 carbon atoms, provided that the number of carbon atoms of the organic thiol-based ligand described above is It does not include the number of carbon atoms of the substituent.
  • the alkyl group may be linear or branched.
  • the organothiol-based ligand is pentanethiol, hexanethiol, heptanethiol, 2,4-dimethylbenzenethiol, 2-phenylethanethiol, glutathione, thiopronin, thiolated poly(ethylene glycol), It may be any one or two or more selected from the group consisting of p-mercaptophenol and (r-mercaptopropyl)-trimethoxysilane), but is not limited thereto.
  • the organic thiol-based ligand SR may be any one or two or more selected from the group consisting of arylthiol having 6 to 30 carbon atoms, heteroaryl thiol having 5 to 30 carbon atoms, arylalkanthiol having 6 to 30 carbon atoms, etc.
  • one or more hydrogens in the functional group may be further substituted or not substituted with a substituent, in which case, the substituent is an alkyl group having 1 to 10 carbon atoms, a halogen group (-F, -Br, -Cl, -I) , A nitro group, a cyano group, a hydroxy group, an amino group, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms or a heterocycloalkyl group having 4 to 20 carbon atoms It is an aryl group, provided that the carbon number of the organic thiol-based ligand described above does not include the carbon number of the substituent.
  • the alkyl group may be linear or branched
  • the organothiol-based ligand may be 2,4-dimethylbenzenethiol.
  • the use of an alkylarylthiol-based compound as a ligand can greatly improve the yield of a silver nanocluster magnetic body doped with a dissimilar metal atom during synthesis.
  • the organothiol-based ligand according to an embodiment of the present invention may be an arylthiol having 6 to 30 carbon atoms in which C1-C10 alkyl is substituted.
  • another aspect of the present invention relates to a method for manufacturing a method of manufacturing a magnetic substance doped with a silver nanocluster of the heterometallic atom, comprising: a) preparing a reaction solution by reacting a silver precursor and an organic thiol-based ligand compound; And b) adding a dissimilar metal precursor, a reaction catalyst, and a reducing agent to the reaction solution to prepare a magnetic nanocluster that satisfies Formula 1 below.
  • SR is an organothiol-based ligand
  • M is ruthenium (Ru) or rhodium (Rh)
  • SR in Formula 1 is the same as described above, and redundant descriptions are omitted.
  • the silver nanoclusters are doped with one ruthenium atom or rhodium atom, so that the intrinsic properties of the doped atoms are maintained as they are, so that a nanocluster magnetic body having excellent magnetic properties can be effectively manufactured.
  • nanocluster magnetic body having the same configuration with 24 silver atoms, 1 heterometal atom, and 18 organothiol-based ligands, and the nanocluster magnetic body prepared accordingly can be completely uniform in size and structure.
  • the spin shape can be very clear.
  • the mixing ratio between the metal precursors, the addition amount of the reducing agent, and the selection of the solvent may be important, and this will be described in detail below.
  • a step of reacting a reaction solution including a silver precursor and an organic thiol-based ligand compound may be performed.
  • the silver precursor may be used without particular limitation as long as it is commonly used in the art, and as a specific example, AgNO 3 , AgBF 4 , AgCF 3 SO 3 , AgClO 4 , AgO 2 CCH 3 and AgPF 6 may be any one or two or more selected from the group consisting of, preferably AgNO 3 is good in improving the synthesis efficiency to use.
  • the organothiol-based ligand compound may be RSH, which is a compound before hydrogen falls compared to the SR, and as a specific example, an alkanethiol having 1 to 30 carbon atoms, an arylthiol having 6 to 30 carbon atoms , C3-C30 cycloalkanethiol, C5-C30 heteroarylthiol, C3-C30 heterocycloalkanethiol, C6-C30 arylalkanethiol, etc.
  • RSH is a compound before hydrogen falls compared to the SR
  • an alkanethiol having 1 to 30 carbon atoms an arylthiol having 6 to 30 carbon atoms
  • C3-C30 cycloalkanethiol C5-C30 heteroarylthiol
  • C3-C30 heterocycloalkanethiol C6-C30 arylalkanethiol
  • one or more hydrogens in the functional group may be further substituted or unsubstituted with a substituent, wherein the substituent is an alkyl group having 1 to 10 carbon atoms, a halogen group (-F, -Br, -Cl, -I ), nitro group, cyano group, hydroxy group, amino group, aryl group having 6 to 20 carbon atoms, alkenyl group having 2 to 7 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heterocycloalkyl group having 3 to 20 carbon atoms or 4 to 20 carbon atoms It is a heteroaryl group, provided that the carbon number of the organic thiol-based ligand described above does not include the carbon number of the substituent.
  • the alkyl group may be linear or branched.
  • the organothiol-based ligand compound is pentanethiol, hexanethiol, heptanethiol, 2,4-dimethylbenzenethiol, 2-phenylethanethiol, glutathione, thiopronin, thiolated poly(ethylene glycol) , p-mercaptophenol and (r-mercaptopropyl)-trimethoxysilane) may be any one or two or more selected from the group consisting of, but is not limited thereto.
  • the organic thiol-based ligand compound SR may be any one or two or more selected from the group consisting of arylthiol having 6 to 30 carbon atoms, heteroaryl thiol having 5 to 30 carbon atoms, arylalkanthiol having 6 to 30 carbon atoms, etc.
  • one or more hydrogens in the functional group may be further substituted or unsubstituted with a substituent, wherein the substituent is an alkyl group having 1 to 10 carbon atoms, a halogen group (-F, -Br, -Cl, -I ), nitro group, cyano group, hydroxy group, amino group, aryl group having 6 to 20 carbon atoms, alkenyl group having 2 to 7 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heterocycloalkyl group having 3 to 20 carbon atoms or 4 to 20 carbon atoms It is a heteroaryl group, provided that the carbon number of the organic thiol-based ligand described above does not include the carbon number of the substituent.
  • the alkyl group may be linear or branched.
  • the organothiol-based ligand compound may be 2,4-dimethylbenzenethiol.
  • the yield of the silver nanocluster magnetic material doped with dissimilar metal atoms can be greatly improved during synthesis.
  • the mixing ratio of the silver precursor and the organic thiol-based ligand compound may be a ratio commonly mixed in the art, and as a specific example, the molar ratio of the silver precursor: the organic thiol-based ligand compound is 1: It may be 1 to 10, more preferably 1: 1.5 to 6, even more preferably 1: 2 to 4. In such a range, the synthesis efficiency is excellent and reaction impurities can be reduced.
  • the reaction solution of step a) may further include a solvent to improve the dissolution and reaction ease of the silver precursor, and the solvent is specifically limited if it is commonly used in the art Can be used without.
  • the solvent is dichloromethane, water, alcohol having 1 to 5 carbon atoms, acetonitrile, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), acetone, tetrahydrofuran (THF) and 1,4- It may be any one or two or more mixed solvents selected from the group consisting of dioxane and the like, preferably methanol, tetrahydrofuran, or a mixed solvent thereof. In this case, 50 to 100 ml of the solvent may be added based on 1 mmol of the silver precursor, but is not limited thereto.
  • b) adding a dissimilar metal precursor, a reaction catalyst, and a reducing agent to the reaction solution to prepare a nanocluster magnetic material satisfying Formula 1 may be performed.
  • the mixing ratio of the silver precursor to the dissimilar metal precursor may be particularly important in manufacturing the silver nanocluster magnetic body doped with dissimilar metal atoms.
  • the molar ratio of the silver precursor: the dissimilar metal precursor may be 50: 0.8 to 1.2, more preferably 50: 0.9 to 1.1, particularly preferably 50: 1.
  • a silver nanocluster magnetic material doped with a dissimilar metal atom can be effectively prepared, and when the number of moles of the dissimilar metal precursor is too large relative to the molar ratio, a reaction in which the silver atom is substituted with a dissimilar metal atom may not be performed.
  • Ru ruthenium
  • the dissimilar metal precursor may be dissolved in the second solvent and added to the reaction solution.
  • the second solvent may be the same as the solvent, and in particular, the second solvent may be a mixed solvent of water and tetrahydrofuran (THF).
  • THF tetrahydrofuran
  • the volume ratio of water: tetrahydrofuran (THF) may be 1: 2 to 8, more preferably 1: 2.5 to 6, and most preferably 1: 3 to 5. Synthesis efficiency may be excellent in this range.
  • the reaction catalyst and the reducing agent may be used without particular limitation as long as they are commonly used in the art, and as a specific example, the reaction catalyst may be tetraphenylphosphine bromide (PPh 4 Br), etc. And, the reducing agent may be NaBH 4 or the like, but is not limited thereto.
  • reaction catalyst may be added in an amount of 0.01 to 0.1 mmol based on 1 mmol of the silver precursor, and the reducing agent may be added in an amount of 1 to 3 mmol based on 1 mmol of the silver precursor, but this is only an example and the present invention is It is not limited.
  • an additional purification process may be further performed to obtain a high-purity nanocluster magnetic material, and the additional purification process may be performed through a conventional method.
  • RuCl 3 was dissolved in 1 ml of a mixed solvent of THF:H 2 O mixed in a volume ratio of 4:1 and added to the reaction solution, and then tetraphenylphosphine bromide (PPh 4 Br) 0.014 mmol (in 0.5 Ml methanol) was added sequentially, and NaBH 4 0.4 mmol (in 0.5 ml H 2 O) was quickly added at once. Then, the mixture was further stirred for 5 hours to synthesize RuAg 24 (SPhMe 2 ) 18 .
  • PPh 4 Br tetraphenylphosphine bromide
  • the mixture was aged for 12 hours, and then the supernatant and the precipitate were separated through centrifugation to dry the precipitate.
  • RhAg 24 SPhMe 2
  • RhAg 24 (SPhMe 2) 18 in each of the electrospray ionization mass spectrometry (ESI-MS) results, showing the measured value that exactly matches the structure RuAg 24 (SPhMe 2) 18, and It was confirmed that RhAg 24 (SPhMe 2 ) 18 was well synthesized as a single substance.
  • RhAg 24 (SPhMe 2 ) 18 , as shown in FIG. 2, Ag 3d peaks appear at 368.2 eV and 374.7 eV, and peak areas Was 19548. The Rh 3d peak appeared at 307.63 eV and 312.33 eV, and the peak area was 1054. The S 2p peak appeared at 162.25 eV and 163.41 eV, and the peak area was 13405. The P 2p peak appeared at 133 eV and 133.87 eV, and the peak area was 1041. When this peak area is expressed as a ratio, it can be expressed as [Rh 1.3 Ag 23.7 (SPhMe 2 ) 17.2 ] 1- (PPh 4 ) 1+ , and it was observed that it has a -1 charge.
  • XPS X-ray photoelectron spectroscopy
  • FIG. 3 and 4 are RuAg 24 (SPhMe 2) 18 and RhAg 24 (SPhMe 2) 18 in each of the 1 H NMR results, as in the XPS results, Figure 3 is [Ru 1 Ag 24 (SPhMe 2 ) 18] 1 - (PPh 4 ) 1+ , FIG. 4 shows the structure of [Rh 1 Ag 24 (SPhMe 2 ) 18 ] 1- (PPh 4 ) 1+ , confirming that the two nanoclusters each have -1 charge. there was.
  • UV-Vis ultraviolet-visible light
  • RhAg 24 (SPhMe 2 ) 18 it was confirmed that characteristic absorption occurs at 1.1 V and 1.82 V, respectively. At this time. The absorption peak near 1 V indicates that the nanocluster is a distortion structure. On the other hand, in the case of RhAg 24 (SPhMe 2 ) 18 , absorption occurred at 1.84 V and 2.51 V, respectively, and no absorption peak appeared near 1 V. Rhodium (Rh)-substituted nanoclusters are also structurally distorted, but absorption at low energy is forbidden, and thus does not appear in UV-Vis absorption.
  • FIG. 6 is a square wave voltamogram analysis data of RuAg 24 (SPhMe 2 ) 18 and RhAg 24 (SPhMe 2 ) 18 , wherein the horizontal axis is voltage (V vs AgQRE), and the vertical axis is current (A).

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Abstract

La présente invention concerne un corps magnétique à nanoagrégats d'argent dopé avec un atome de métal différent, et son procédé de préparation, et peut fournir: un corps magnétique de nanoagrégat d'argent dopé avec un atome de métal différent, ayant d'excellentes caractéristiques magnétiques, ayant une taille et une structure complètement uniformes de façon à avoir une forme de spin très claire, et ayant une excellente dispersibilité dans une solution; et son procédé de préparation.
PCT/KR2020/005428 2019-04-26 2020-04-24 Corps magnétique à nanoagrégats d'argent dopé avec un atome de métal different, et son procédé de préparation WO2020218871A1 (fr)

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KR20190049049 2019-04-26
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KR1020200049638A KR102266900B1 (ko) 2019-04-26 2020-04-23 이종금속 원자가 도핑된 은 나노클러스터 자성체 및 이의 제조 방법
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4342838A (en) * 1980-03-31 1982-08-03 Exxon Research & Engineering Co. Bimetallic clusters of ruthenium with copper, silver and gold

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4342838A (en) * 1980-03-31 1982-08-03 Exxon Research & Engineering Co. Bimetallic clusters of ruthenium with copper, silver and gold

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BOOTHARAJU, MEGALAMANE S., JOSHI CHAKRA P., PARIDA MANAS R., MOHAMMED OMAR F., BAKR OSMAN M.: "Templated atom-precise galvanic synthesis and structure elucidation of a [Ag24Au(SR)18]- nanocluster", ANGEWANDTE CHEMIE, vol. 55, no. 3, 18 January 2016 (2016-01-18), pages 922 - 926, XP055758452, DOI: 10.1002/anie.201509381 *
KWAK, KYUJU, TANG QING, KIM MINSEOK, JIANG DE-EN, LEE DONGIL: "Interconversion between superatomic 6-electron and 8-electron configurations of M@Au24(SR)18 clusters (M= Pd, Pt", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 137, no. 33, August 2015 (2015-08-01), pages 10833 - 10840, XP055758446, DOI: 10.1021/jacs.5b06946 *
RODRIGUEZ-KESSLER, P. L., PAN SUDIP, FLOREZ ELIZABETH, CABELLOS JOSÉ LUIS, MERINO GABRIEL: "Structural Evolution of the Rhodium-Doped Silver Clusters AgnRh(n?15) and Their Reactivity toward NO", THE JOURNAL OF PHYSICAL CHEMISTRY C, vol. 121, no. 35, 2017, pages 19420 - 19427, XP055758448, DOI: 10.1021/acs.jpcc.7b05048 *
WANG, ZHI, SENANAYAKE RAVITHREE, AIKENS CHRISTINE M., CHEN WEN-MIAO, TUNG CHEN-HO, SUN DI: "Gold-doped silver nanocluster [Au3Ag38(SCH2Ph)24X5]2-(X= Cl or Br)", NANOSCALE, vol. 8, no. 45, 2016, pages 18905 - 18911, XP055758443, DOI: 10.1039/C6NR06615A *

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