CN107021975A - Monokaryon dysprosium complex by part of the oxyquinoline of 2 methyl, 5,7 dichloro 8 and its preparation method and application - Google Patents
Monokaryon dysprosium complex by part of the oxyquinoline of 2 methyl, 5,7 dichloro 8 and its preparation method and application Download PDFInfo
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- CN107021975A CN107021975A CN201710276935.6A CN201710276935A CN107021975A CN 107021975 A CN107021975 A CN 107021975A CN 201710276935 A CN201710276935 A CN 201710276935A CN 107021975 A CN107021975 A CN 107021975A
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- methyl
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- dichloro
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- oxyquinoline
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 229910052692 Dysprosium Inorganic materials 0.000 title claims abstract description 16
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 229960003540 oxyquinoline Drugs 0.000 title abstract description 8
- 125000003963 dichloro group Chemical group Cl* 0.000 title abstract description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 title abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 230000005291 magnetic effect Effects 0.000 claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 7
- HNUFDBQIXGQAEX-UHFFFAOYSA-N 2-chloroquinolin-8-ol Chemical compound C1=C(Cl)N=C2C(O)=CC=CC2=C1 HNUFDBQIXGQAEX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 230000006698 induction Effects 0.000 abstract description 8
- 239000000696 magnetic material Substances 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 23
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 22
- 239000005297 pyrex Substances 0.000 description 22
- 239000013078 crystal Substances 0.000 description 16
- 238000012512 characterization method Methods 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000000547 structure data Methods 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229960002172 chlorquinaldol Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000005641 tunneling Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- 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
- H01F1/42—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties of organic or organo-metallic materials, e.g. graphene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a kind of monokaryon dysprosium complex using the oxyquinoline of 2 methyl, 5,7 dichloro 8 as part and its preparation method and application.The chemical formula of the complex is：[Dy(L)3(HL)], wherein, L be the oxyquinoline of 25,7 dichloro of methyl 8 slough hydroxyl hydrogen atom, one unit negative charge of band；HL is the oxyquinoline of 2 methyl, 5,7 dichloro 8；The complex belongs to anorthic system, the space groups of P 1.The preparation method of complex of the present invention is：Take Dy (NO3)3·6H2O and the oxyquinoline of 25,7 dichloro of methyl 8, are dissolved with methanol, adjust pH=6.5~7.8 of resulting solution, and gained mixed liquor is produced in being reacted under heating condition.The complex preparation method that the present invention is provided is simple, with low cost, reproducible, the slow relaxation magnetic behavior of field induction is shown as at low temperature, available for preparing magnetic material.
Description
Technical field
The present invention relates to a kind of monokaryon dysprosium complex and its system using 2- methyl-DHQ as part
Preparation Method and application, belong to technical field of magnetic materials.
Background technology
Single molecular magnetses show slow relaxation, quantum tunneling and quantum Interference etc. solely due to the particularity of structure
Special magnetic phenomenon, makes it have potential application prospect in terms of quantum computer, super-high density information storage material.
Further investigation along with researcher to single molecular magnetses relaxation mechanism, while quick with characterization technique
Develop, the increasing rare earth single molecular magnetses with practical value are synthesized, but had not yet to see chemical formula and be
[Dy(C10H6NOCl2)3(C10H7NOCl2)] magnetic material relevant report.
The content of the invention
The technical problem to be solved in the present invention is to provide it is a kind of it is new using 2- methyl-DHQ as with
Monokaryon dysprosium complex of body and its preparation method and application.
It is of the present invention with 2- methyl -5,7- dichloro-8-hydroxyquinoline be part monokaryon dysprosium complex, the complex
Chemical formula be：[Dy(L)3(HL)], wherein, L be 2- methyl -5,7- dichloro-8-hydroxyquinolines slough hydroxyl hydrogen atom, band one
Individual unit negative charge；HL is 2- methyl-DHQ；
The complex belongs to anorthic system, P-1 space groups, and cell parameter is α=87.889 (5) °, β=80.540 (6) °, γ=67.372 (6) °.
2- methyl -5, the 7- dichloro-8-hydroxyquinolines being related in above-mentioned technical proposal, may be referred to existing literature (such as
JiantongCui,Synthesis of chlorquinaldol,Zhongguo Yiyao Gongye Zazhi,39(2008),
733；Either Oleg V.Larionov, Direct, catalytic, and regioselective synthesis of 2-
alkyl-,aryl-,and alkenyl-substituted N-heterocycles from N-oxides,Organic
Letters, 16 (2014), 864-867) etc. the method for report prepared, can also the synthesis of designed, designed scheme, can also be straight
Connect purchase.
The molecular formula of monokaryon dysprosium complex of the present invention using 2- methyl-DHQ as part
For C40H25Cl8DyN4O4, molecular weight is 1071.5.
The crystal knot of monokaryon dysprosium complex of the present invention using 2- methyl-DHQ as part
As described in Table 1, part bond distance's bond angle data are as described in Table 2 for structure data.
Table 1：[Dy(L)3(HL) crystallographic parameter]
Table 2：[Dy(L)3(HL) part bond distance]Bond angle (°) table
Applicants have found that, it is of the present invention with monokaryon dysprosium of 2- methyl -5,7- dichloro-8-hydroxyquinoline for part
The magnetic property of complex shows as slow relaxation magnetic behavior.Therefore, present invention additionally comprises above-mentioned with the chloro- 8- of 2- methyl -5,7- bis-
Oxyquinoline is application of the monokaryon dysprosium complex of part in magnetic material is prepared.
The preparation method of the above-mentioned monokaryon dysprosium complex using 2- methyl-DHQ as part is：Take Dy
(NO3)3·6H2O and 2- methyl -5,7- dichloro-8-hydroxyquinolines, are dissolved with methanol, adjust resulting solution pH=6.5~
7.8, gained mixed liquor is produced in being reacted under heating condition.
In above-mentioned preparation method, the Dy (NO3)3·6H2The mol ratio of O and 2- methyl-DHQ
For stoichiometric proportion, usually 4：1.
In above-mentioned preparation method, methanol is used as solvent, and its consumption can be determined as needed, generally can dissolve participation
The raw material of reaction is advisable, specifically, to be calculated on the basis of 1mmol 2- methyl -5,7- dichloro-8-hydroxyquinolines, whole raw materials
Total consumption of mixed solvent used is generally 6~8mL., can be by Dy (NO in the step of specific dissolving3)3·6H2O and 2- first
Base -5,7- dichloro-8-hydroxyquinoline is dissolved with solvent respectively, is remixed and is reacted together, also can be by Dy (NO3)3·6H2O and 2-
Solubilizer dissolves again after methyl-DHQ mixing.Applicant has found in process of the test, only when using first
Alcohol is generated as title complex is just had during solvent.
In above-mentioned preparation method, the pH value of solution can be adjusted using existing conventional alkaline matter, preferably used
Triethylamine adjusts the pH value of solution.In technical scheme of the present invention, pH=6.8~7.3 of solution are preferably adjusted.
It is typically that the mixed liquor for adjusting gained after pH value is placed in container, after liquid nitrogen frozen in above-mentioned preparation method
Vacuum is evacuated to, is sealed, is placed under heating condition and reacts again afterwards.The reaction is preferably carried out under the conditions of 60~100 DEG C,
The time reacted under the conditions of said temperature is usually 30~80h or more than 80h；It will preferably control in the reaction time
System is in 60~80h.Reaction is more preferably carried out under the conditions of 80~100 DEG C.The heavy wall hard glass generally closed using one end
Pipe adjusts the mixed liquor of gained after pH value to contain.
Compared with prior art, the invention provides it is a kind of it is new with 2- methyl -5,7- dichloro-8-hydroxyquinoline for part
Monokaryon dysprosium complex [Dy (L)3(HL)] and preparation method thereof, applicant is in research it has also been found that the complex is showed at low temperature
For slow relaxation magnetic behavior, it can be used for preparing magnetic material；In addition, the preparation method of the complex is simple, with low cost, repeat
Property is good.
Brief description of the drawings
Fig. 1 is [Dy (L) made from the embodiment of the present invention 13(HL) structure chart]；
Fig. 2 is [Dy (L) made from the embodiment of the present invention 13(HL) infrared spectrogram]；
Fig. 3 is [Dy (L) made from the embodiment of the present invention 13(HL) χ]m, χmT-T curve maps；
Fig. 4 is [Dy (L) made from the embodiment of the present invention 13(HL) M-H curve maps]；
Fig. 5 is [Dy (L) made from the embodiment of the present invention 13(HL) exchange curve map].
Embodiment
With reference to specific embodiment, the present invention is described in further detail, to more fully understand present disclosure, but
The present invention is not limited to following examples.
2- methyl-the DHQ being related in following embodiment is prepared using following methods：
The oxyquinoline of 0.1mol 2- methyl -8 is added in the cold glacial acetic acid of 100mL, then 0.05mol dichloros sea
Because being divided into two parts, it is added portionwise in the glacial acetic acid solution of substrate.After every part adds, continue to react in ice-water bath.It is anti-after 3h
It should terminate, reaction solution is poured into frozen water, constantly stir, obtain the precipitation of yellow.Suction filtration, filter cake rinses three with frozen water
It is secondary, dried under normal temperature, obtain the solid of yellow.Crude product recrystallizing methanol, obtains the chloro- 8- of target product 2- methyl -5,7- bis-
Oxyquinoline.Elementary analysis (%) (C10H7NOCl2), experiment value:C, 52.93, H, 3.10, N, 6.06；Theoretical value:C, 52.63,
H, 3.07, N, 6.14.
Embodiment 1
By 92mg (about 0.4mmol) part 2- methyl-DHQ and 46mg (about 0.1mmol) Dy
(NO3)3·6H2O is added to one end closing and is about in 18cm Pyrex pipes, adds 1.2mL methanol, 2 drop triethylamines is added dropwise (now molten
Liquid pH value is 7.0), Pyrex pipes to be vacuumized, by its another end closure.It is incubated under the conditions of the Pyrex pipes sealed are placed in into 80 DEG C
72h is reacted, takes out, naturally cools to room temperature, Pyrex bottom of the tube, which can be observed, there are red bulk crystals to separate out.Yield 70.6%.
Above-mentioned products therefrom is characterized：
1) crystal structure analysis：
Determine the intact red bulk crystals of surface texture to determine its crystal structure, gained crystal knot by single crystal diffraction
Structure data as shown in foregoing table 1, bond distance's bond angle data as shown in Table 2 above, gained red bulk crystals chemical constitution such as Fig. 1
It is shown, it is determined that gained red bulk crystals are title complex [Dy (L)3(HL)], wherein, L be 2- methyl -5,7- bis- it is chloro-
8-hydroxyquinoline sloughs the negative electrical charge of phenolic hydroxyl group hydrogen atom one unit of band, and HL is 2- methyl -5,7- dichloro-8-hydroxyquinolines；
The molecular formula of the monokaryon dysprosium complex is C40H25Cl8DyN4O4, molecular weight is 1071.5.Fig. 2 is the infrared light of gained complex
Spectrogram.
2) magnetic property is determined：
Take [the Dy (L) of complex made from 0.032g the present embodiment3(HL) magnetic is carried out after] pulverizing in magnetic measurement system
Test, shown in the exchange curve such as Fig. 5 (including the real and imaginary parts of exchange are to curve of temperature) for obtaining complex, complex
χM, χMT-T curve maps and M-H figures difference are as shown in Figure 3 and Figure 4.
As shown in Figure 5, in low temperature part, the test exchange off field outside certain direct current finds that real and imaginary parts have bright
Simultaneously there is signal peak in aobvious frequency dependent behavior, it was demonstrated that it is of the present invention with 2- methyl -5,7- dichloro-8-hydroxyquinoline be with
The monokaryon dysprosium complex [Dy (L) of body3(HL) the slow relaxation magnetic behavior of field induction] is shown as at low temperature.
Comparative example 1
Embodiment 1 is repeated, unlike：Methanol is replaced with water as solvent.
Taking out Pyrex and managing and naturally cool to has the precipitation of yellow strip product in Pyrex pipes after room temperature.Take products therefrom
The structural characterizations such as single crystal diffraction are carried out, it is not title complex described herein to learn products therefrom.
Comparative example 2
Embodiment 1 is repeated, unlike：Solvent is changed to be made up of chloroform and water, total consumption is constant, wherein chloroform and
The volume ratio of water is 1：1.
Take out Pyrex to manage and naturally cool to the solution after room temperature in Pyrex is managed for clarification, and there are no solid product
Separate out.
Comparative example 3
Embodiment 1 is repeated, unlike：Solvent is changed to be made up of first alcohol and water, total consumption is constant, wherein methanol and
The volume ratio of water is 1：1.
Take out Pyrex to manage and naturally cool to the solution after room temperature in Pyrex is managed for clarification, and there are no solid product
Analysis.
Embodiment 2
Embodiment 1 is repeated, unlike：By 2- methyl-DHQ and Dy (NO3)3·6H2O distinguishes
Dissolved, then remixed together with 0.6mL methanol, reacted again after regulation pH.
Taking out Pyrex and manage and naturally cool to after room temperature in Pyrex bottom of the tube has the precipitation of red bulk crystals.Yield
67%.
Structural characterization is carried out to products therefrom, is defined as title complex [Dy (L)3(HL)].To the magnetics of products therefrom
Property representation understands that products therefrom shows as the slow relaxation magnetic behavior of field induction at low temperature.
Embodiment 3
Embodiment 1 is repeated, unlike：80h will be extended in reaction time.
Taking out Pyrex and manage and naturally cool to after room temperature in Pyrex bottom of the tube has the precipitation of red bulk crystals.Yield
71%.
Structural characterization is carried out to products therefrom, is defined as title complex [Dy (L)3(HL)].To the magnetics of products therefrom
Property representation understands that products therefrom shows as the slow relaxation magnetic behavior of field induction at low temperature.
Embodiment 4
Embodiment 1 is repeated, unlike：90h will be extended in reaction time.
Taking out Pyrex and manage and naturally cool to after room temperature in Pyrex bottom of the tube has the precipitation of red bulk crystals.Yield
66%.
Structural characterization is carried out to products therefrom, is defined as title complex [Dy (L)3(HL)].To the magnetics of products therefrom
Property representation understands that products therefrom shows as the slow relaxation magnetic behavior of field induction at low temperature.
Embodiment 5
Embodiment 1 is repeated, unlike：Reaction temperature is changed to 70 DEG C.
Taking out Pyrex and manage and naturally cool to after room temperature in Pyrex bottom of the tube has the precipitation of red bulk crystals.Yield
63%.
Structural characterization is carried out to products therefrom, is defined as title complex [Dy (L)3(HL)].To the magnetics of products therefrom
Property representation understands that products therefrom shows as the slow relaxation magnetic behavior of field induction at low temperature.
Embodiment 6
Embodiment 1 is repeated, unlike：Reaction temperature is changed to 100 DEG C, 30h will be changed in the reaction time.
Taking out Pyrex and manage and naturally cool to after room temperature in Pyrex bottom of the tube has the precipitation of red bulk crystals.Yield
62%.
Structural characterization is carried out to products therefrom, is defined as title complex [Dy (L)3(HL)].To the magnetics of products therefrom
Property representation understands that products therefrom shows as the slow relaxation magnetic behavior of field induction at low temperature.
Embodiment 7
Embodiment 1 is repeated, unlike：Reaction temperature is changed to 40 DEG C, 60h will be changed in the reaction time.
Taking out Pyrex and manage and naturally cool to after room temperature in Pyrex bottom of the tube has the precipitation of red bulk crystals.Yield
55%.
Structural characterization is carried out to products therefrom, is defined as title complex [Dy (L)3(HL)].To the magnetics of products therefrom
Property representation understands that products therefrom shows as the slow relaxation magnetic behavior of field induction at low temperature.
Claims (6)
1. with the monokaryon dysprosium complex that 2- methyl -5,7- dichloro-8-hydroxyquinoline is part, it is characterised in that：
The chemical formula of the complex is：[Dy(L)3(HL)], wherein, L be 2- methyl -5,7- dichloro-8-hydroxyquinolines slough hydroxyl
Hydrogen atom, one unit negative charge of band；HL is 2- methyl-DHQ；
The complex belongs to anorthic system, P-1 space groups, and cell parameter is α=87.889 (5) °, β=80.540 (6) °, γ=67.372 (6) °.
2. the preparation method of complex described in claim 1, it is characterised in that：Take Dy (NO3)3·6H2O and 2- methyl -5,7- two
Chloro-8-hydroxyquinoline, is dissolved with methanol, adjusts pH=6.5~7.8 of resulting solution, gained mixed liquor is in anti-under heating condition
Should, produce.
3. preparation method according to claim 2, it is characterised in that：Reaction is carried out under the conditions of 60~100 DEG C.
4. preparation method according to claim 2, it is characterised in that：The time of reaction is 30~80h or more than 80h.
5. preparation method according to claim 2, it is characterised in that：The pH value of solution is adjusted with triethylamine.
6. the monokaryon dysprosium complex using 2- methyl-DHQ as part described in claim 1 is preparing magnetic
Application in property material.
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| CN201710276935.6A CN107021975B (en) | 2017-04-21 | 2017-04-21 | Using 2- methyl -5,7-dichloro-8-hydroxyquinoline as monokaryon dysprosium complex of ligand and its preparation method and application |
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| CN201710276935.6A CN107021975B (en) | 2017-04-21 | 2017-04-21 | Using 2- methyl -5,7-dichloro-8-hydroxyquinoline as monokaryon dysprosium complex of ligand and its preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110950800A (en) * | 2019-10-12 | 2020-04-03 | 广西师范大学 | Rare earth complex constructed based on 2-methyl-5, 7-dibromo-8-hydroxyquinoline and preparation method and application thereof |
| CN110981898A (en) * | 2019-10-12 | 2020-04-10 | 广西师范大学 | Low-toxicity rare earth complex and preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110950800A (en) * | 2019-10-12 | 2020-04-03 | 广西师范大学 | Rare earth complex constructed based on 2-methyl-5, 7-dibromo-8-hydroxyquinoline and preparation method and application thereof |
| CN110981898A (en) * | 2019-10-12 | 2020-04-10 | 广西师范大学 | Low-toxicity rare earth complex and preparation method and application thereof |
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