CN103864820A - Organic-inorganic hybridization molecular magnet with room-temperature metallicity and preparation method thereof - Google Patents
Organic-inorganic hybridization molecular magnet with room-temperature metallicity and preparation method thereof Download PDFInfo
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- CN103864820A CN103864820A CN201410072055.3A CN201410072055A CN103864820A CN 103864820 A CN103864820 A CN 103864820A CN 201410072055 A CN201410072055 A CN 201410072055A CN 103864820 A CN103864820 A CN 103864820A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 238000009396 hybridization Methods 0.000 title claims abstract description 10
- -1 alcohol compound Chemical class 0.000 claims abstract description 21
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 17
- QYCVHILLJSYYBD-UHFFFAOYSA-L copper;oxalate Chemical compound [Cu+2].[O-]C(=O)C([O-])=O QYCVHILLJSYYBD-UHFFFAOYSA-L 0.000 claims abstract description 17
- 239000013078 crystal Substances 0.000 claims abstract description 14
- 239000008151 electrolyte solution Substances 0.000 claims abstract description 12
- 238000003487 electrochemical reaction Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 239000011669 selenium Substances 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- UFPVYWYEZPMUQL-UHFFFAOYSA-N 2-(1,3-diselenol-2-ylidene)-1,3-diselenole Chemical compound [Se]1C=C[Se]C1=C1[Se]C=C[Se]1 UFPVYWYEZPMUQL-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 230000005415 magnetization Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000238366 Cephalopoda Species 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002887 superconductor Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920000314 poly p-methyl styrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 206010063401 primary progressive multiple sclerosis Diseases 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
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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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Power Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses an organic-inorganic hybridization molecular magnet with room-temperature metallicity and a preparation method of the molecular magnet. The molecular formula of the molecular magnet with the room-temperature metallicity is BETS3[Cu2(C2O4)3]B2, wherein BETS represents disulfo-diethylene tetraselenafulvalene; and B represents an alcohol compound. The preparation method of the molecular magnet with the metallicity comprises the step of performing electrochemical reaction on an ammonium salt of cupric oxalate with BETS in an electrochemical tank by taking the alcohol compound as an electrolyte solution so as to obtain the molecular magnet with the room-temperature metallicity on an anode. According to the preparation method of the molecular magnet with the room-temperature metallicity, single crystal of the molecular magnet with room-temperature metallicity is prepared in an organic solvent system from an organic pi electron system and Jahn-Teller distorted magnetic anion. The molecular magnet with room-temperature metallicity, which is provided by the invention, is good in crystal quality, single in product and high in yield.
Description
The application is the divisional application that application number is 201210209161.2, the applying date is on June 20th, 2012, invention and created name is " organic inorganic hybridization room temperature metallicity molecular magnet and preparation method thereof ".
Technical field
The present invention relates to metallic molecular magnet of a kind of organic inorganic hybridization room temperature and preparation method thereof.
Background technology
Molecular based material due to its light weight, can carry out molecular designing bringing into play huge advantage in preparation NEW TYPE OF COMPOSITE functional materials.The room temperature molecular magnet that have conductivity (partly lead, metal), air-stable, occurs long-range magnetic order in room temperature is because its wide application prospect at molecule spintronics is the target that international material scholar, physicist, chemist pursue.
Up to the present the V (TCNE) that, Jin You U.S. J.S.Miller reports in the world
2(CH
2cl
2)
0.5(Manriquez, J.M.; Yee, G.T.; McLean, R.S.; Epstein, A.J.; Miller, J.S.; Science1991,252,1415) and [Cr of French M.Verdaguer seminar report
5(CN)
12] .10H
2two room temperature molecular magnets of O (Mallah, T., Thiebaut, S., Verdaguer, M., Veillet, P.Science1993,262,1554) are admitted by international counterparts.What they adopted is to stir preparation precipitation after raw material being mixed in solution, product is all unstable in air, and can only be precipitated, the crystalline structure of pure phase is up to the present all unclear, and the explanation of all magnetic properties relevant to material is all also to depend on imaginary structure to carry out.This has limited the understanding of the intrinsic performance of people to room temperature molecular magnet and the application of material.Although V (TCNE)
2(CH
2cl
2)
0.5at room temperature specific conductivity is 10
-3scm
– 1, belong to semi-conductor, up to the present metallic room temperature magnet has no report.
Cu – O, Co – O, the Mn – O octahedron of Jahn-Teller distortion play decisive role in inorganic ceramic superconductor phase and giant magnetic resistance.By O wherein
2 –use isoelectronic species C
2o
4 2 –replace, can in molecular system, realize some characteristic of inorganic ceramic superconductor and giant magnetic resistance.One of them important goal is exactly the metallic molecular magnet of room temperature.
Summary of the invention
The object of this invention is to provide metallic molecular magnet of a kind of organic inorganic hybridization room temperature and preparation method thereof.
The ammonium salt of a kind of cupric oxalate provided by the invention, its molecular formula is: M
2cu (C
2o
4)
2a
x; In formula, M represents alkyl substituted ammonium ion, and A represents H
2o or alcohol compound, x is 1 or 2.
In the ammonium salt of above-mentioned cupric oxalate, M specifically can be (CH
3)
4n
+, (CH
3)
3nH
+, (CH
3)
2nH
2 +, (C
2h
5)
2nH
2 +, (C
2h
5)
2(CH
3) NH
+, (C
3h
7)
3nH
+or (C
2h
5)
3nH
+deng ammonium ion.
In the ammonium salt of above-mentioned cupric oxalate, described alcohol compound specifically can be methyl alcohol or ethanol.
The present invention also provides the preparation method of the ammonium salt of above-mentioned cupric oxalate, comprises the steps: M
2(C
2o
4), H
2c
2o
42H
2o and Cu (OH)
2in described alcohol compound, react, after completion of the reaction, through concentrating and obtain product.
In above-mentioned method, described M
2(C
2o
4), H
2c
2o
42H
2o and Cu (OH)
2molfraction ratio can be (1～6): (1～6): 1, specifically can be 1:1:1 or 6:6:1.
In above-mentioned method, the temperature of described reaction can be 20 ℃～80 ℃, specifically can be 20 ℃ or 80 ℃, and the time can be 0.2h～1h, specifically can be 0.2h or 1h.
In above-mentioned method, under agitation condition, by Cu (OH)
2be added to described M
2(C
2o
4) and H
2c
2o
42H
2in the solution of the alcohol compound of O.
The metallic molecular magnet of a kind of organic inorganic hybridization room temperature provided by the present invention, its molecular formula is: BETS
3[Cu
2(C
2o
4)
3] B
2, wherein, BETS represents dithio diethyl support group four selenium fulvalenes, and its structural formula is suc as formula shown in I, and B represents alcohol compound;
The metallic molecular magnet of above-mentioned room temperature, described alcohol compound specifically can be methyl alcohol or ethanol.
The preparation method of the metallic molecular magnet of above-mentioned room temperature provided by the present invention, comprise the steps: take described alcohol compound as electrolyte solution, the ammonium salt of above-mentioned cupric oxalate and BETS carry out electrochemical reaction in electrochemical cell, obtain the metallic molecular magnet crystal of described room temperature on anode.
In above-mentioned method, described electrolyte solution also comprises chlorobenzene; Described chlorobenzene can be (4～10) with the volume parts ratio of described alcohol compound: 1, specifically can be 5:1.
In above-mentioned method, the ammonium salt of described cupric oxalate and the molfraction of BETS ratio can be (10～1000): 1, specifically can be 10:1 or 11:1.
In above-mentioned method, the ammonium salt of described cupric oxalate and the proportioning of described electrolyte solution are: described in every 1mmol, the ammonium salt of cupric oxalate needs electrolyte solution described in (1～2000) ml, and as described in 1mmol, the ammonium salt of cupric oxalate needs electrolyte solution as described in 320ml or 343ml.
In above-mentioned method, described anode is platinum electrode; The diameter of described anode can be 1mm～2mm, as 1mm.
In above-mentioned method, the electric current of controlling described electrochemical reaction can be 0.20 μ A～1.00 μ A, as 0.70 μ A.
The preparation method of the metallic molecular magnet of room temperature provided by the invention, from the magnetic anion of organic π-electron system and Jahn-Teller distortion, prepares the metallic molecular magnet monocrystalline of organic inorganic hybridization room temperature at organic solvent system; The crystal mass of the metallic molecular magnet of organic inorganic hybridization room temperature provided by the invention is good, and product is single, and yield is high.
Accompanying drawing explanation
Fig. 1 is the photo of the metallic molecular magnet of room temperature for preparing in the embodiment of the present invention 1.
Fig. 2 is the specific conductivity graphic representation of the metallic molecular magnet of room temperature for preparing in the embodiment of the present invention 1.
Fig. 3 is the Advances in crystal X-ray diffraction figure of the metallic molecular magnet of room temperature for preparing in the embodiment of the present invention 1.
Fig. 4 is the metallic molecular magnet of the room temperature DC magnetization rate curve figure in 2～300K under different magnetic field intensity preparing in the embodiment of the present invention 1.
Fig. 5 is the metallic molecular magnet of room temperature for preparing in the embodiment of the present invention 1 isothermal magnetization rate curve figure in 2～300K.
Fig. 6 is the metallic molecular magnet of room temperature for preparing in the embodiment of the present invention 1 isothermal magnetization rate curve figure in 2～300K.
Embodiment
The experimental technique using in following embodiment if no special instructions, is ordinary method.
Material, reagent etc. used in following embodiment, if no special instructions, all can obtain from commercial channels.
(1) prepare two (vinyl dithio) the four selenium fulvalenes of BETS()
Method according to report in document (T.Courcet, I.Malfant, K.Pokhodnia, P.Cassoux, New.J.Chem.1998,22,585-589) is prepared, and response path is as follows:
The equation of the first step reaction is as follows:
1,1-diethoxy-2-monobromethane and dithioglycol react and prepare 2,3-dihydro-Isosorbide-5-Nitrae-bis-thiophene English (dithia benzene) in toluene solvant; Yield is 38%.
The equation of second step reaction is as follows:
Set out from 2,3-dihydro-Isosorbide-5-Nitrae-dithia benzene, under anhydrous and oxygen-free operation, prepare sap green titanium compound, yield is 46%.
The equation of three-step reaction is as follows:
By gained Ti compound and (Cl
3cO)
2cO reaction prepares ketone compounds, and yield is about 54%.
The equation of four-step reaction is as follows:
Gained ketone compounds and triethyl oxygen phosphorus reaction can be prepared to two (vinyl dithio) four selenium fulvalenes, and yield is 50%.
(2) prepare the ammonium salt [(C of one dimension cupric oxalate
2h
5)
3nH]
2cu (C
2o
4)
2(H
2o)
By the Cu of 2mmol (OH)
2under heated and stirred, be added to the [(C of 2mmol
2h
5)
3nH]
2(C
2o
4) and 2mmolH
2c
2o
42H
2(wherein, [(C in the methanol solution of O
2h
5)
3nH]
2(C
2o
4), H
2c
2o
4.2H
2o and Cu (OH)
2molfraction than for 1:1:1), obtain blue look solution; At 20 ℃, react after 1h, obtain containing H through concentrating
2the blueness [(C of O
2h
5)
3nH]
2cu (C
2o
4)
2crystal, yield is 90%.
(3) by 40mg[(C
2h
5)
3nH]
2cu (C
2o
4)
2(H
2o)
2be dissolved in 5ml anhydrous methanol, add 5mg BETS(wherein, [(C
2h
5)
3nH]
2cu (C
2o
4)
2(H
2o)
2compare for 10:1 with the molfraction of BETS) to electrochemical cell; Under anhydrous and oxygen-free operation, the chlorobenzene solution of 25ml purifying is added (in this system, chlorobenzene with the volume parts of methyl alcohol than being 5:1, every 1mmol[(C
2h
5)
3nH]
2cu (C
2o
4)
2(H
2o)
2need 343ml electrolyte solution); Electric current is located to 0.70 μ A, after several weeks, can obtains brown tabular crystal BETS at platinum anode (diameter phi 1mm)
3[Cu
2(C
2o
4)
3] (CH
3oH)
2, as shown in Figure 1, yield approximately 80%.
With gold size, spun gold is connected on the monocrystalline of above-mentioned preparation with four point probe method on Quantum Design PPMS physical measurement instrument, the crystal of above-mentioned preparation is carried out to electric conductivity test, as shown in Figure 2, the specific conductivity of the metallic molecular magnet room temperature of this room temperature is 140S to test result
cm
– 1.
On Nonius Kappa CCD, carry out Advances in crystal X-ray diffraction experiment with Mo K alpha-ray, as shown in Figure 3, the room temperature crystallographic parameter of gained crystal is as follows:
α=104.873 (1) °, β=102.284 (1) °, γ=92.349 (2) °,
z=2, D
c.=2.429g/cm
3, μ (Mo, K α)=8.787mm
– 1, 29212measured data, 9783unique, R
int=0.0626, R
1=0.0722for4504observation of I>=2 σ (I
0), wR2=0.2459for all data, GOF=1.001.In an independent zones, there are three independently BETS molecules, two Cu, three oxalates and two solvent molecules.
On Quantum Design SQUID magnetic measurement instrument, measure metallic magnet DC magnetic rate in 2～300K under different magnetic field intensity of above-mentioned preparation, as shown in Figure 4.
The isothermal magnetization rate of the metallic magnet of having measured above-mentioned preparation on SQUID magnetic measurement instrument in 2～300K, magnetic hysteresis raises and reduces with temperature, observes 100Oe magnetic hysteresis, as shown in Figure 5 and Figure 6 at 300K.
(1) prepare two (vinyl dithio) the four selenium fulvalenes of BETS()
Preparation method is with step (1) in embodiment 1.
(2) prepare the ammonium salt [(C of one dimension cupric oxalate
2h
5)
2(CH
3) NH]
2cu (C
2o
4)
2(H
2o)
By the Cu of 2mmol (OH)
2under heated and stirred, be added to the [(C of 12mmol
2h
5)
2(CH
3) NH]
2(C
2o
4) and 12mmol H
2c
2o
42H
2(wherein, [(C in the methanol solution of O
2h
5)
2(CH
3) NH]
2(C
2o
4), H
2c
2o
42H
2o and Cu (OH)
2molfraction than for 6:6:1), obtain blue look solution; At 80 ℃, react after 0.2h, obtain containing H through concentrating
2the blueness [(C of O
2h
5)
2(CH
3) NH]
2cu (C
2o
4)
2(H
2o) crystal, yield is 85%.
(3) by 40mg[(C
2h
5)
2(CH
3) NH]
2cu (C
2o
4)
2(H
2o) be dissolved in 5ml anhydrous methanol, add 5mgBETS(wherein, [(C
2h
5)
2(CH
3) NH]
2cu (C
2o
4)
2(H
2o) be 11:1 with the molfraction ratio of BETS) to electrochemical cell; Under anhydrous and oxygen-free operation will: the chlorobenzene solution of 25ml purifying add (in this system, chlorobenzene with the volume parts of methyl alcohol than being 5:1, every 1mmol[(C
2h
5)
2(CH
3) NH]
2cu (C
2o
4)
2(H
2o) need 320ml electrolyte solution); Electric current is located to 0.7 μ A, after several weeks, can obtains brown tabular crystal BETS at platinum anode (diameter phi 1mm)
3[Cu
2(C
2o
4)
3] (CH
3oH)
2, as shown in Figure 1, yield approximately 80%.
The character of crystal prepared by the character of the metallic molecular magnet of room temperature prepared by the present embodiment and embodiment 1 is without substantial differences.
Claims (6)
1. the metallic molecular magnet of organic inorganic hybridization room temperature, its molecular formula is: BETS
3[Cu
2(C
2o
4)
3] B
2, wherein, BETS represents dithio diethyl support group four selenium fulvalenes, B represents alcohol compound.
2. the metallic molecular magnet of room temperature according to claim 1, is characterized in that: described alcohol compound is methyl alcohol or ethanol.
3. the preparation method of the metallic molecular magnet of room temperature described in claim 1 or 2, comprise the steps: take described alcohol compound as electrolyte solution, the ammonium salt of cupric oxalate and BETS carry out electrochemical reaction in electrochemical cell, obtain the metallic molecular magnet crystal of described room temperature on anode;
The ammonium salt of described cupric oxalate, its molecular formula is: M
2cu (C
2o
4)
2a
x; In formula, M represents alkyl substituted ammonium ion, and A represents H
2o or alcohol compound, x is 1 or 2.
4. method according to claim 3, is characterized in that: M is (CH
3)
4n
+, (CH
3)
3nH
+, (CH
3)
2nH
2 +, (C
2h
5)
2nH
2 +, (C
2h
5)
2(CH
3) NH
+, (C
3h
7)
3nH
+or (C
2h
5)
3nH
+; Described alcohol compound is methyl alcohol or ethanol.
5. according to the method described in claim 3 or 4, it is characterized in that: described electrolyte solution also comprises chlorobenzene; Described chlorobenzene is (4～10) with the volume parts ratio of described alcohol compound: 1; The ammonium salt of described cupric oxalate and the molfraction of BETS are than being (10～150): 1; The ammonium salt of described cupric oxalate and the proportioning of described electrolyte solution are: every 1mm
oelectrolyte solution described in the ammonium salt of cupric oxalate needs (1～20) ml described in l.
6. according to the method described in claim 3 or 4, it is characterized in that: described anode is platinum electrode; The diameter of described anode is 1mm～2mm; The electric current of controlling described electrochemical reaction is 0.20 μ A～1.00 μ A.
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2012
- 2012-06-20 CN CN201410072055.3A patent/CN103864820B/en active Active
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