CN107021974A - Monokaryon dysprosium complex by part of the oxyquinoline of 2 methyl, 5,7 dibromo 8 and its preparation method and application - Google Patents
Monokaryon dysprosium complex by part of the oxyquinoline of 2 methyl, 5,7 dibromo 8 and its preparation method and application Download PDFInfo
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- CN107021974A CN107021974A CN201710268732.2A CN201710268732A CN107021974A CN 107021974 A CN107021974 A CN 107021974A CN 201710268732 A CN201710268732 A CN 201710268732A CN 107021974 A CN107021974 A CN 107021974A
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- 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 System
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic System without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
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- 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
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- 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
Abstract
The invention discloses a kind of monokaryon dysprosium complex using the oxyquinoline of 2 methyl, 5,7 dibromo 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 dibromo of methyl 8 slough hydroxyl hydrogen atom, one unit negative charge of band；HL is the oxyquinoline of 2 methyl, 5,7 dibromo 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 dibromo of methyl 8, are dissolved with methanol, adjust pH=6.0~7.5 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, and slow relaxation magnetic behavior 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 -5,7- dibromc-8-hydroxyquinolines 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(C10H6NOBr2)3(C10H7NOBr2)] 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 -5,7- dibromc-8-hydroxyquinolines as with
Monokaryon dysprosium complex of body and its preparation method and application.
Monokaryon dysprosium complex of the present invention using 2- methyl -5,7-D-Br-8-HQ as part, the complex
Chemical formula be：[Dy(L)3(HL)], wherein, L be 2- methyl -5,7-D-Br-8-HQ slough hydroxyl hydrogen atom, band one
Individual unit negative charge；HL is 2- methyl -5,7- dibromc-8-hydroxyquinolines；
The complex belongs to anorthic system, P-1 space groups, and cell parameter is α=87.926 (10) °, β=80.611 (10) °, γ=67.404 (9) °.
2- methyl-the 5,7-D-Br-8-HQ 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) synthesized.
The molecular formula of monokaryon dysprosium complex of the present invention using 2- methyl -5,7- dibromc-8-hydroxyquinolines as part
For C40H25Br8DyN4O4, molecular weight is：1427.42.
The crystal knot of monokaryon dysprosium complex of the present invention using 2- methyl -5,7- dibromc-8-hydroxyquinolines 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, the monokaryon dysprosium of the present invention using 2- methyl -5,7-D-Br-8-HQ as part
The magnetic property of complex shows as slow relaxation magnetic behavior.Therefore, present invention additionally comprises above-mentioned with the bromo- 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 -5,7- dibromc-8-hydroxyquinolines as part is：Take Dy
(NO3)3·6H2O and 2- methyl -5,7-D-Br-8-HQ, is dissolved with methanol, adjust resulting solution pH=6.0~
7.5, 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 -5,7- dibromc-8-hydroxyquinolines
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, is calculated on the basis of 1mmol 2- methyl -5,7-D-Br-8-HQ, whole raw materials
Total consumption of polar solvent used is generally 8~10mL., can be by Dy (NO in the step of specific dissolving3)3·6H2O and 2- first
Base -5,7-D-Br-8-HQ 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 the mixing of methyl -5,7- dibromc-8-hydroxyquinolines.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=6.5~7.1 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 a kind of new using 2- methyl -5,7-D-Br-8-HQ as 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 -5,7- the dibromc-8-hydroxyquinolines being related in following embodiment are 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 dibromos 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.Elementary analysis (%) (C10H7NOBr2), experiment value:
C, 37.93, H, 2.20, N, 4.46；Theoretical value:C, 37.97, H, 2.22, N, 4.43.
Embodiment 1
By 92mg (about 0.4mmol) part 2- methyl -5,7- dibromc-8-hydroxyquinolines 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 CH3OH, is added dropwise 2 and drips Et3N is (now molten
Liquid pH value is 6.8), 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 is about
69%.
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 bromo-
8-hydroxyquinoline sloughs hydroxyl hydrogen atom, one unit negative charge of band；HL is 2- methyl -5,7-D-Br-8-HQ, the list
The molecular formula of core dysprosium complex is C40H25Br8DyN4O4, molecular weight is 1427.42.The infrared spectrum of complex is as shown in Figure 2.
2) magnetic property is determined：
Take [the Dy (L) of complex made from 0.033g 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 curve maps difference are as shown in Figure 3 and Figure 4.
As shown in Figure 5, in low temperature part, the exchange real and imaginary parts of complex have obvious dependent behavior to frequency,
Confirm the monokaryon dysprosium complex [Dy (L) of the present invention using 2- methyl -5,7- dibromc-8-hydroxyquinolines as part3(HL)]
Slow relaxation magnetic behavior is shown as at low temperature.
Comparative example 1
Embodiment 1 is repeated, unlike：The methanol in embodiment 1 is replaced with water as solvent.
Taking-up Pyrex is managed and naturally cooled to and manages interior in Pyrex after room temperature and there are no solid product precipitation, for clarification
Solution, i.e., no target product generation.
Comparative example 2
Embodiment 1 is repeated, unlike：The methanol in embodiment 1 is replaced with ethanol as solvent.
Taking-up Pyrex is managed and naturally cooled to and manages interior in Pyrex after room temperature and there are no solid product precipitation, for clarification
Solution, i.e., no target product generation.
Comparative example 3
Embodiment 1 is repeated, unlike：The methanol in embodiment 1 is replaced with chloroform as solvent.
Taking-up Pyrex is managed and naturally cooled to and manages interior in Pyrex after room temperature and there are no solid product precipitation, for clarification
Solution, i.e., no target product generation.
Embodiment 2
Embodiment 1 is repeated, unlike：
By Dy (NO3)3·6H2O and 2- methyl -5,7-D-Br-8-HQ is dissolved with 0.6mL methanol respectively, then
Remix together, 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
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 slow relaxation magnetic behavior 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
70%.
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 slow relaxation magnetic behavior 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
68%.
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 slow relaxation magnetic behavior at low temperature.
Embodiment 5
Embodiment 1 is repeated, unlike：Reaction temperature is changed to 90 DEG C, 80h 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
65%.
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 slow relaxation magnetic behavior at low temperature.
Embodiment 6
Embodiment 1 is repeated, unlike：Reaction temperature is changed to 100 DEG C, 80h 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
61%.
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 slow relaxation magnetic behavior at low temperature.
Embodiment 7
Embodiment 1 is repeated, unlike：
Reaction temperature is changed to 60 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
65%.
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 slow relaxation magnetic behavior at low temperature.
Embodiment 8
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
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 slow relaxation magnetic behavior at low temperature.
Claims (6)
1. the monokaryon dysprosium complex by part of 2- methyl -5,7-D-Br-8-HQ, it is characterised in that：
The chemical formula of the complex is：[Dy(L)3(HL)], wherein, L be 2- methyl -5,7-D-Br-8-HQ slough hydroxyl
Hydrogen atom, one unit negative charge of band；HL is 2- methyl -5,7- dibromc-8-hydroxyquinolines；
The complex belongs to anorthic system, P-1 space groups, and cell parameter is α=87.926 (10) °, β=80.611 (10) °, γ=67.404
(9)°。
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
Bromo- 8-hydroxyquinoline, is dissolved with methanol, adjusts pH=6.0~7.5 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 -5,7- dibromc-8-hydroxyquinolines as part described in claim 1 is preparing magnetic
Application in property material.
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Cited By (4)
| 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 |
| CN111072727A (en) * | 2019-12-23 | 2020-04-28 | 广西师范大学 | Iridium complex constructed based on 8-hydroxyquinoline derivative and 2-phenylpyridine iridium dimer as well as synthetic method and application thereof |
| CN111116667A (en) * | 2019-12-23 | 2020-05-08 | 广西师范大学 | Iridium complex constructed based on 8-hydroxyquinoline derivative and 1-phenylpyrazole iridium dimer as well as synthetic method and application thereof |
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| CN110950861B (en) * | 2019-11-01 | 2021-04-06 | 广西师范大学 | Mononuclear dysprosium complex with 1, 10-phenanthroline-2, 9-dicarboxylic acid as ligand and preparation method and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CN111072727A (en) * | 2019-12-23 | 2020-04-28 | 广西师范大学 | Iridium complex constructed based on 8-hydroxyquinoline derivative and 2-phenylpyridine iridium dimer as well as synthetic method and application thereof |
| CN111116667A (en) * | 2019-12-23 | 2020-05-08 | 广西师范大学 | Iridium complex constructed based on 8-hydroxyquinoline derivative and 1-phenylpyrazole iridium dimer as well as synthetic method and application thereof |
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