CN106966972B - A kind of dysprosium complex constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand and its synthetic method and application - Google Patents
A kind of dysprosium complex constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand and its synthetic method and application Download PDFInfo
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- CN106966972B CN106966972B CN201710357125.3A CN201710357125A CN106966972B CN 106966972 B CN106966972 B CN 106966972B CN 201710357125 A CN201710357125 A CN 201710357125A CN 106966972 B CN106966972 B CN 106966972B
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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
- C07D215/30—Metal salts; Chelates
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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 dysprosium complex constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand and its synthetic method and applications.The chemical formula of the complex is [Dy (HL) (L)], and wherein L is that the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- sloughs a hydrogen atom on hydroxyl hydrogen atom and acylhydrazone nitrogen, the negative electrical charge of two units of band；HL is that the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- sloughs hydroxyl hydrogen atom, one unit negative charge of band.The synthetic method of the complex are as follows: take Dy (NO3)3·6H2The chloro- benzoyl hydrazone of O and 2- Formyl-8-hydroxyquinoline -2-, is dissolved with mixed solvent, adjusts pH=7.9~8.5 of acquired solution, and gained mixed liquor reacts under heating condition, and reactant is cooling, there is crystal to be precipitated to get.Complex provided by the invention shows as the slow relaxation magnetic behavior of field induction at low temperature, can be used for preparing magnetic material.
Description
Technical field
The present invention relates to a kind of dysprosium complex constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand and its synthetic methods
And application, belong to technical field of magnetic materials.
Background technique
In recent years, with the fast development of quantum calculation and information technology revolution, nano magnetic material has been subjected to more next
The more concern of polyvoltine researcher.Derived from single molecular magnets in high density information processing and storage, quantum computer, molecular spin
The potential application of electronics etc., the design and synthesis of single molecular magnets have become physics, chemistry, material in the latest 20 years
The primary study object in the fields such as science.The wherein rare-earth base single molecular magnets single electron number relatively more because rare earth ion has and aobvious
The magnetic anisotropy of work becomes the research hotspot in current single molecular magnets field.By development in more than 20 years, single molecular magnets
Research also make great progress.But the research in relation to rare earth single molecular magnets still suffers from many challenges: how gram
Rare earth ion quantum tunneling effect due to caused by magnetization is taken, effective energy barrier of rare earth single molecular magnets how is improved, illustrates
The relaxation mechanism etc. of rare earth single molecular magnets.The energy barrier of rare earth single molecular magnets not only with the ground state spin values of metal ion itself
It is closely related with magnetic anisotropy and closely related with the symmetry of the entirety of molecule and part.
Single molecular magnets are because high density information processing is with storage, quantum calculation, molecular spin in terms of
Potential application becomes the research hotspot in the fields such as chemistry, physics, material science.Research finds the change by organic ligand structure
Change or the variation of substituent group can play the purpose for effectively regulating and controlling single molecular magnets property.Although relevant research has taken
Very big progress is obtained, but there is presently no unified explanation, single molecular magnets knots for the magnetic action mechanism of single molecular magnets
Relationship between structure and magnetism is still the mainstream of single molecular magnets research field at this stage.With the rapid development of information technology,
Scientists have researched and proposed higher requirement to nano magnetic material and its various performance parameters, it is more and more have it is real
It is synthesized with the magnetic material of value, but having had not yet to see molecular formula is C34H21Cl2DyN6O4With 8-hydroxyquinoline
Acyl hydrazone derivative is the relevant report for the dysprosium complex that ligand is constructed.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of structure novel with 8-hydroxyquinoline acyl hydrazone derivative be with
The dysprosium complex and its synthetic method and application that body is constructed.
The dysprosium complex of the present invention constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand, the chemistry of the complex
Formula are as follows: [Dy (HL) (L)], wherein L is that the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- sloughs hydroxyl hydrogen atom and acylhydrazone
A hydrogen atom on nitrogen, the negative electrical charge of two units of band；HL is that the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- is sloughed
Hydroxyl hydrogen atom, one unit negative charge of band；
The complex belongs to anorthic system, P-1 space group, cell parameter are as follows: α=92.060 (11) °, β=114.040 (7) °, γ=97.309 (8) °.
The chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- involved in above-mentioned technical proposal can refer to existing text
(Liu Yong-chun, Yang Zheng-yin, Eur.J.Med.Chem., 2009,44 (12), 5080-5089) are offered to be closed
At structural formula is shown below:
The molecular formula of the dysprosium complex of the present invention constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand is
C34H21Cl2DyN6O4, molecular weight 810.97.
The crystal structural data of the dysprosium complex of the present invention constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand
As described in Table 1, part bond distance bond angle data are as described in Table 2.
Table 1:[Dy (HL) (L)] crystallographic parameter
a R1=Σ | | Fo|–|Fc||/Σ|Fo|.b wR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
Table 2:[Dy (HL) (L)] part bond distanceBond angle (°) table
Applicants have found that the dysprosium complex of the present invention constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand
Magnetic property show as slow relaxation magnetic behavior.Therefore, the invention also includes it is above-mentioned with 8-hydroxyquinoline acyl hydrazone derivative be with
The dysprosium complex that body is constructed is preparing the application in magnetic material.
The synthetic method of the above-mentioned dysprosium complex constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand are as follows: take Dy
(NO3)3·6H2The chloro- benzoyl hydrazone of O and 2- Formyl-8-hydroxyquinoline -2-, is dissolved with mixed solvent, adjusts acquired solution
PH=7.9~8.5, gained mixed liquor react under heating condition, and reactant is cooling, have crystal to be precipitated to get target product；Its
In, the mixed solvent is the composition of first alcohol and water.
In above-mentioned synthetic method, the in the mixed solvent, the volume ratio of first alcohol and water can be any proportion, preferably
1~3:1~3 are preferably selected as 3:1,2:1 or 1:1.The dosage of the mixed solvent can determine as needed, usually with energy
The raw material that reaction is participated in dissolution is advisable.Specifically, it is with the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- of 0.1mmol
Total dosage of benchmark, mixed solvent used in whole raw materials is generally 3~5mL.It, can be by Dy in specific the step of dissolving
(NO3)3·6H2The chloro- benzoyl hydrazone of O and 2- Formyl-8-hydroxyquinoline -2- uses one of mixed solvent ingredient to dissolve respectively,
It remixes and reacts together, it can also be by Dy (NO3)3·6H2After the chloro- benzoyl hydrazone mixing of O and 2- Formyl-8-hydroxyquinoline -2-
Again plus mixed solvent dissolves.
In above-mentioned synthetic method, the pH value of solution can be adjusted using existing common alkaline matter, is preferably used
The pH value of triethylamine adjusting solution.In technical solution of the present invention, pH=8.1~8.3 of solution are preferably adjusted.
In above-mentioned synthetic method, resulting mixed liquor is placed in container after will usually adjusting pH value, after liquid nitrogen frozen
It is evacuated to vacuum, is sealed, is placed under heating condition reacts again later.The reaction preferably carries out under the conditions of 60~120 DEG C,
The time reacted under the conditions of above-mentioned temperature is usually 30~80h, can also be greater than 80h；It will preferably control in the reaction time
In 60~80h.Reaction more preferably carries out under the conditions of 80~100 DEG C.Generally use heavy wall horminess glass tube closed at one end
To contain resulting mixed liquor after adjusting pH value.
Compared with prior art, the present invention provides a kind of structure novels using 8-hydroxyquinoline acyl hydrazone derivative as ligand
The dysprosium complex and its synthetic method constructed, synthetic method are simple, low in cost, reproducible；Applicant also sends out under study for action
Slow relaxation magnetic behavior now is shown as under the complex low temperature, can be used for preparing magnetic material.
Detailed description of the invention
Fig. 1 is the infrared of the chloro- benzoyl hydrazone of ligand 2- Formyl-8-hydroxyquinoline -2- that various embodiments of the present invention use
Spectrogram；
Fig. 2 is the infrared spectrogram of final product made from the embodiment of the present invention 1；
Fig. 3 is the structure chart of final product made from the embodiment of the present invention 1；
Fig. 4 is the χ of final product made from the embodiment of the present invention 1m-T,χmT-T curve graph；
Fig. 5 is the M-H curve graph of final product made from the embodiment of the present invention 1；
Fig. 6 is the exchange curve graph of final product made from the embodiment of the present invention 1；
Fig. 7 is the thermal multigraph of final product made from the embodiment of the present invention 1.
Specific embodiment
The present invention is described in further detail combined with specific embodiments below, content to better understand the invention, but
The present invention is not limited to following embodiments.
The chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- involved in following embodiment is closed using following methods
At:
The chloro- benzoyl hydrazine of 2- (2mmol, 0.313g) and 2- aldehyde radical -8-hydroxyquinoline (2mmol, 0.34g) are dissolved in respectively
In the dehydrated alcohol of 30mL and 70mL, 6 drop glacial acetic acid, heating, to temperature liter are added into the round-bottomed flask equipped with benzoyl hydrazine
When height is to 80 DEG C, aldehyde radical containing 2- -8-hydroxyquinoline ethanol solution is slowly added dropwise, continues heating reflux reaction 6h, stops reaction,
It is cooled to room temperature, after decompression extracts solvent, is successively washed several times with ethyl alcohol, ether, obtains target product 2- formyl after dry
The chloro- benzoyl hydrazone of base -8-hydroxyquinoline -2-.Elemental analysis (%) (C of gained target product17H12N3O2Cl) experiment value: C,
62.65, H, 3.82, N, 12.88；Theoretical value: C, 62.68, H, 3.71, N, 12.90.Its infrared spectroscopy is as shown in Figure 1.
Embodiment 1
Take the chloro- benzoyl hydrazone (0.025mmol, 8.1mg) of ligand 2- Formyl-8-hydroxyquinoline -2- and Dy (NO3)3·
6H2O (0.025mmol, 11.4mg) is added in the Pyrex pipe for being about 18cm closed at one end, and 0.9mL CH is added3OH and
0.3mL H2O is added dropwise triethylamine 1 and drips, and gently oscillation shakes up (pH=8.1 of solution at this time), will pipe under conditions of vacuumizing
Another end closure takes out, Pyrex pipe is tightly wrapped up with cotton-wool drops it slowly later as insulation reaction 72h under the conditions of 80 DEG C
To room temperature, peony web crystal is precipitated, yield is about 17% (calculating with Dy).Elemental analysis (%) (C34H21Cl2DyN6O4),
Experiment value: C, 50.28, H, 2.74, N, 10.35；Theoretical value: C, 50.35, H, 2.61, N, 10.36.
1 products therefrom of embodiment is characterized:
1) IR Characterization:
With 360 FT-IR type Fourier transformation infrared spectrometer (KBr tabletting) of U.S. Nicolet, the present embodiment is made
Product carry out infrared analysis, take the photograph 4000~400cm of spectral limit-1, gained infrared spectrum spectrogram is as shown in Fig. 2, data are as follows:
IR(KBr,cm-1): 1589 (s), 1487 (m), 1337 (m), 1104 (s), 1060 (s), 905 (w), 835 (w), 743
(s), 480 (w).
2) crystal structure analysis:
The intact peony web crystal of surface texture is measured by agilent company SuperNova single crystal diffractometer
To determine its mono-crystalline structures, resulting structures data are shown in aforementioned table 1, and bond distance's bond angle data are shown in that aforementioned table 2, the dark red color strip-shaped of gained are brilliant
The chemical structure of body is as shown in figure 3, determine that resulting peony web crystal is of the present invention with 8-hydroxyquinoline acylhydrazone
Derivative is the dysprosium complex [Dy (HL) (L)] that ligand is constructed, and wherein L is the chloro- benzoyl of 2- Formyl-8-hydroxyquinoline -2-
Hydrazone sloughs a hydrogen atom on hydroxyl hydrogen atom and acylhydrazone nitrogen, the negative electrical charge of two units of band；HL is 2- formoxyl -8- hydroxyl
The chloro- benzoyl hydrazone of quinoline -2- sloughs hydroxyl hydrogen atom, one unit negative charge of band.The molecular formula of the complex is
C34H21Cl2DyN6O4, molecular weight 810.97.
3) magnetic property measures:
Magnetic is carried out on Magnetic Test instrument after taking dysprosium complex made from 30.6mg the present embodiment [Dy (HL) (L)] to pulverize
Property test, obtain the χ of complexM-T,χMT-T curve graph as shown in figure 4, M-H curve graph as shown in figure 5, complex magnetic susceptibility hand over
The real and imaginary parts of stream are as shown in Figure 6 to the curve graph of temperature.
By Fig. 4 and Fig. 5 it is found that dysprosium complex of the present invention [Dy (HL) (L)] temperature be the section 2-300K in, directly
Under the conditions of stream external magnetic field is 1000Oe, in 300K, χMThe value of T is maximum, is 14.78cm3K mol-1, a Dy only to spin
(III) ion, theoretical value 14.17cm3K mol-1, (6H15/2, S=5/2, L=5, g=4/3, C=14.17cm3K mol-1),
The a little higher than theoretical value of experiment value of dysprosium complex of the present invention.With the reduction of temperature, χMThe value of T gradually decreases, later χMT
Value decline rapidly suddenly, when temperature reaches 2K, χMThe value of T is minimized value, is 10.81cm3K mol-1。
It will be appreciated from fig. 6 that the real and imaginary parts of exchange have apparent frequency dependent behavior, it was demonstrated that this hair in low temperature part
The bright dysprosium complex [Dy (HL) (L)] constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand is shown as slowly at low temperature
Relaxation magnetic behavior.
4) thermogravimetric characterizes:
With French C1-esteraseremmer-N La Mu Instrument Ltd. Labsys evo TG-DSC/DTA, dysprosium made from the present embodiment is matched
It closes object [Dy (HL) (L)] and carries out thermogravimetric analysis, by thermogravimetric analysis it is found that the solvent molecule that crystal structure outer layer does not dissociate, and
There is no solvent molecule and anion to participate in coordination.At 400 DEG C, frame starts gradually to disintegrate, when temperature rises to 1000 DEG C,
The 70.7% of gross mass, residue 29.3% are lost, residue may be the oxide Dy of dysprosium2O3(theoretical value 29.9%).Its heat
Weight analysis curve graph is as shown in fig. 7, the stability of dysprosium complex of the present invention is good as shown in Figure 7.
Comparative example 1
Embodiment 1 is repeated, unlike: mixed solvent is changed to be made of second alcohol and water, the volume ratio of second alcohol and water
Total dosage for 1:1, mixed solvent is constant.
Pyrex pipe is taken out, Pyrex pipe is tightly wrapped up with cotton-wool makes it be slowly dropped to room temperature, no solid product or crystal analysis
Out, it is still precipitated without solid product or crystal after standing 10 days, i.e., no target product generates.
Comparative example 2
Embodiment 1 is repeated, unlike: mixed solvent is changed to be made of acetonitrile and water, the volume ratio of acetonitrile and water
Total dosage for 1:1, mixed solvent is constant.
Pyrex pipe is taken out, Pyrex pipe is tightly wrapped up with cotton-wool makes it be slowly dropped to room temperature, no solid product or crystal analysis
Out, it is still precipitated without solid product or crystal after standing 10 days, i.e., no target product generates.
Comparative example 3
Embodiment 1 is repeated, unlike: mixed solvent is changed to be made of chloroform and water, chloroform and water
Volume ratio be 1:3, total dosage of mixed solvent is constant.
Pyrex pipe is taken out, Pyrex pipe is tightly wrapped up with cotton-wool makes it be slowly dropped to room temperature, no solid product or crystal analysis
Out, it is still precipitated without solid product or crystal after standing 10 days, i.e., no target product generates.
Embodiment 2
Embodiment 1 is repeated, unlike:
It 1) is 2:1 by the ratio of in the mixed solvent first alcohol and water, total dosage of mixed solvent is constant；
3) pH value of solution is adjusted to 8.2.
Pyrex pipe is taken out, Pyrex pipe is tightly wrapped up with cotton-wool makes it be slowly dropped to room temperature, and Pyrex bottom of the tube has peony
Web crystal is precipitated.Yield 22%.
Structural characterization is carried out to products therefrom, determines that product is target product [Dy (HL) (L)], wherein L is 2- formoxyl-
The chloro- benzoyl hydrazone of 8-hydroxyquinoline -2- sloughs a hydrogen atom on hydroxyl hydrogen atom and acylhydrazone nitrogen, the negative electricity of two units of band
Lotus；HL is that the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- sloughs hydroxyl hydrogen atom, one unit negative charge of band.
Show as the slow relaxation magnetic row of field induction at low temperature to products therefrom known to the Magnetic Characterization of products therefrom
For.
Embodiment 3
Embodiment 1 is repeated, unlike:
It 1) is 1:3 by the ratio of in the mixed solvent first alcohol and water, total dosage of mixed solvent is constant；
2) pH value of solution is adjusted to 8.3；
3) reaction temperature is changed to 60 DEG C, the reaction time is changed to 80h.
Pyrex pipe is taken out, Pyrex pipe is tightly wrapped up with cotton-wool makes it be slowly dropped to room temperature, and Pyrex bottom of the tube has peony
Web crystal is precipitated.Yield 25%.
Structural characterization is carried out to products therefrom, determines that product is target product [Dy (HL) (L)], wherein L is 2- formoxyl-
The chloro- benzoyl hydrazone of 8-hydroxyquinoline -2- sloughs a hydrogen atom on hydroxyl hydrogen atom and acylhydrazone nitrogen, the negative electricity of two units of band
Lotus；HL is that the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- sloughs hydroxyl hydrogen atom, one unit negative charge of band.
Show as the slow relaxation magnetic row of field induction at low temperature to products therefrom known to the Magnetic Characterization of products therefrom
For.
Embodiment 4
Embodiment 1 is repeated, is different from:
1) pH value of solution is adjusted to 8.5；
2) reaction temperature is changed to 120 DEG C, the reaction time is changed to 30h.
Pyrex pipe is taken out, Pyrex pipe is tightly wrapped up with cotton-wool makes it be slowly dropped to room temperature, and Pyrex bottom of the tube has peony
Web crystal is precipitated.Yield 18%.
Structural characterization is carried out to products therefrom, determines that product is target product [Dy (HL) (L)], wherein L is 2- formoxyl-
The chloro- benzoyl hydrazone of 8-hydroxyquinoline -2- sloughs a hydrogen atom on hydroxyl hydrogen atom and acylhydrazone nitrogen, the negative electricity of two units of band
Lotus；HL is that the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2- sloughs hydroxyl hydrogen atom, one unit negative charge of band.
Show as the slow relaxation magnetic row of field induction at low temperature to products therefrom known to the Magnetic Characterization of products therefrom
For.
Claims (7)
1. a kind of dysprosium complex constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand, it is characterised in that:
The chemical formula of the complex are as follows: [Dy (HL) (L)], wherein L is de- for the chloro- benzoyl hydrazone of 2- Formyl-8-hydroxyquinoline -2-
Remove a hydrogen atom on hydroxyl hydrogen atom and acylhydrazone nitrogen, the negative electrical charge of two units of band；HL is 2- formoxyl -8- hydroxyl quinoline
The chloro- benzoyl hydrazone of quinoline -2- sloughs hydroxyl hydrogen atom, one unit negative charge of band；
The complex belongs to anorthic system, P-1 space group, cell parameter are as follows: α=92.060 (11) °, β=114.040 (7) °, γ=97.309
(8)°。
2. the synthetic method of dysprosium complex described in claim 1, it is characterised in that: take Dy (NO3)3·6H2O and 2- formoxyl -8-
The chloro- benzoyl hydrazone of oxyquinoline -2-, is dissolved with mixed solvent, adjusts pH=7.9~8.5 of acquired solution, gained mixed liquor in
It is reacted under heating condition, reactant is cooling, has crystal to be precipitated to get target product；Wherein, the mixed solvent be methanol and
The composition of water.
3. synthetic method according to claim 2, it is characterised in that: the in the mixed solvent, the volume of first alcohol and water
Than for 1~3:1~3.
4. synthetic method according to claim 2, it is characterised in that: reaction carries out under the conditions of 60~120 DEG C.
5. synthetic method according to claim 2, it is characterised in that: the time of reaction is 30~80h or is greater than 80h.
6. synthetic method according to claim 2, it is characterised in that: adjust the pH value of solution with triethylamine.
7. the dysprosium complex described in claim 1 constructed using 8-hydroxyquinoline acyl hydrazone derivative as ligand is preparing magnetic material
In application.
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