CN106810496A - A kind of 8 oxyquinoline nickel complexes and preparation method thereof - Google Patents
A kind of 8 oxyquinoline nickel complexes and preparation method thereof Download PDFInfo
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- CN106810496A CN106810496A CN201710114516.2A CN201710114516A CN106810496A CN 106810496 A CN106810496 A CN 106810496A CN 201710114516 A CN201710114516 A CN 201710114516A CN 106810496 A CN106810496 A CN 106810496A
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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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Abstract
The application belongs to metal complex field, and in particular to a kind of 8 oxyquinoline nickel complex and preparation method thereof.The invention provides a kind of 8 oxyquinoline nickel complex, it has structure shown in formula (I), with good anti-ferromagnetism, and good thermal stability, can be applied in photoelectric properties study on regulation field as antiferromagnet.Present invention also offers the above-mentioned preparation method with anti-ferromagnetic complex, preparation process is simple, and raw material sources extensively, are capable of achieving large-scale production, with wide Commercial Prospect.
Description
Technical field
The invention belongs to metal complex field, and in particular to a kind of 8-hydroxyquinoline nickel complex and preparation method thereof.
Background technology
Supramolecular chemistry be in recent years one it is emerging before modern age chemistry, material science and life science joint
Along science.Supermolecule concept is applied to solid matter self assembly then for the design and crystal engineering of crystal are provided more effectively
Method, the design synthesis of coordination polymer is the new approach that crystal engineering is provided for the design of new supramolecular structure.
The physicochemical properties and performance of the structures shape material of material, physicochemical properties and performance are the reflections of the structure of matter, only
There is the structure for being fully understood by material, could deeply be appreciated and understood by the performance of material, could preferably improve compound and material
Nature and function, design the new compound and material of function admirable.Therefore, to the analysis and research of crystal structure and rationally
Emphasis of the prediction as crystal engineering research.
Coordination polymer because of its special structure, and absorption with separate, be catalyzed, molecule and ion exchange, molecule magnetic
Property, it is luminous there is potential application value with the aspect such as non-linear, just more and more paid attention to, therefore design and synthesize newly
The coordination polymer of type has become a focus.8-hydroxyquinoline part is a flexible and changeable part, is matched somebody with somebody with various
Position mode, can form the complex of stabilization with transition metal or rare earth ion.Proposed 8-hydroxyquinoline from Kodak Company
After aluminium is used as the emitting layer material in electroluminescent device, this quasi-molecule is constantly subjected to organic electroluminescence device academia and work
The extensive attention of industry.In addition, people also attempt introducing functional group by the different parts in 8-hydroxyquinoline, then pass through
With the metal complex that different metal coordination obtains difference in functionality, the discovery 8-hydroxyquinoline class complex such as Ghosh can be potential
It is applied to the treatment of Parkinson disease.Therefore, the different work(obtained as part using 8-hydroxyquinoline class compound are furtherd investigate
Can metal complex, can not only field of coordinative chemistry for we provide more more novel structural models, more can be in optics
The many aspects such as element exploitation, bionics techniques, biologic inorganic and drug development play a role.
The content of the invention
In view of this, it is provided by the present invention the invention provides a kind of 8-hydroxyquinoline nickel complex and preparation method thereof
8-hydroxyquinoline nickel complex there is good anti-ferromagnetism and heat endurance.
Concrete technical scheme of the invention is as follows：
The invention provides a kind of 8-hydroxyquinoline nickel complex, with the structure as shown in formula I：
Present invention also offers a kind of preparation method of above-mentioned 8-hydroxyquinoline nickel complex, including：
A) 8- hydroxyls quinaldine and P-methoxybenzal-dehyde are reacted in reaction dissolvent, is obtained reaction intermediate；
B) reaction intermediate for obtaining step a) reacts with pyridine, water successively, obtains part；
C) part and nickel salt for obtaining step b) are reacted in reaction dissolvent, are obtained the 8-hydroxyquinoline nickel and are matched somebody with somebody
Compound.
Preferably, reaction dissolvent described in step a) is acetic anhydride.
Preferably, the condition of reaction is described in step a)：It is heated to reflux under the protection of inert gas；
The inert gas includes nitrogen, argon gas or helium；
The temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h.
Preferably, in step b) after pyridine is added first heating stirring, then add water and be heated at reflux.
Preferably, the temperature of the heating stirring is 90~100 DEG C, and the time is 20~30min；
The temperature being heated at reflux is 135~140 DEG C, and the time is 22~24h.
Preferably, nickel salt includes described in step c)：One kind or many in nickel nitrate, nickel sulfate, hydrochloric acid nickel and nickel phosphate
Kind；
The mol ratio of the part and nickel salt is (8~12):(25~35).
Preferably, reaction dissolvent described in step c) is the mixed solution of DMF and methyl alcohol；
The ratio of the part and N,N-dimethylformamide is 1mmol:(20~30) mL；
The mixed volume ratio of the N,N-dimethylformamide and methyl alcohol is 1:(2~4).
Preferably, the temperature reacted described in step c) is 80~90 DEG C.
The invention provides a kind of 8-hydroxyquinoline nickel complex, it has structure shown in formula (I), with good anti-iron
Magnetic, and good thermal stability, can be applied in photoelectric properties study on regulation field as antiferromagnet.The present invention is also provided
The above-mentioned preparation method with anti-ferromagnetic complex, preparation process is simple, and raw material sources extensively, are capable of achieving large-scale
Production, with wide Commercial Prospect.
Brief description of the drawings
In order to illustrate more clearly about the embodiment of the present invention or technical scheme of the prior art, below will be to embodiment or existing
The accompanying drawing to be used needed for having technology description is briefly described, it should be apparent that, drawings in the following description are only this
Inventive embodiment, for those of ordinary skill in the art, on the premise of not paying creative work, can also basis
The accompanying drawing of offer obtains other accompanying drawings.
Fig. 1 is the infrared spectrogram of 8-hydroxyquinoline nickel complex obtained in embodiment 1；
Fig. 2 is the crystal structure figure of 8-hydroxyquinoline nickel complex obtained in embodiment 1；
Fig. 3 is the thermogravimetric analysis figure of 8-hydroxyquinoline nickel complex obtained in embodiment 1；
Fig. 4 is the magnetic detection figure of 8-hydroxyquinoline nickel complex obtained in embodiment 1.
Specific embodiment
The invention provides a kind of 8-hydroxyquinoline nickel complex, with the structure as shown in formula I：
In the present invention, the 8-hydroxyquinoline nickel complex belongs to monoclinic system；
Its crystal parameters is：Space group be C12/c1 (15), Z=4,α=90 °,β=90.2130 (10),γ=90 °,
Present invention also offers a kind of preparation method of above-mentioned 8-hydroxyquinoline nickel complex, including：
A) 8- hydroxyls quinaldine and P-methoxybenzal-dehyde are reacted in reaction dissolvent, are obtained reaction intermediate,
The chemical name of the reaction intermediate is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8- acetoxyl group quinoline；
Wherein, the reaction equation being related in step a) is as follows：
B) reaction intermediate for obtaining step a) reacts with pyridine, water successively, obtains part, the chemical name of the part
It is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8-hydroxyquinoline；
Wherein, the reaction equation being related in step b) is as follows：
C) part and nickel salt for obtaining step b) are reacted in reaction dissolvent, are obtained the 8-hydroxyquinoline nickel and are matched somebody with somebody
Compound, its molecular formula is：C108H78F6N6O12Ni3；
Wherein, the reaction equation being related in step c) is as follows：
In the present invention, the reaction dissolvent employed in step a) is preferably acetic anhydride；
The condition of the reaction is：It is heated to reflux under the protection of inert gas.
Further, the addition of 8- hydroxyls quinaldine is 1.25~1.35g, and the addition of P-methoxybenzal-dehyde is
1.2~1.3g；
The temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h；
The inert gas is preferably nitrogen, argon gas or helium, more preferably nitrogen.
In the present invention, in step b) after pyridine is added first heating stirring, then add water and be heated at reflux.
Further, the temperature of the heating stirring is 90~100 DEG C, and the time is 20~30min；
The temperature being heated at reflux is 135~140 DEG C, and the time is 22~24h.
In the present invention, nickel salt described in step c) is preferably the one kind in nickel nitrate, nickel sulfate, hydrochloric acid nickel and nickel phosphate
Or various, more preferably nickel nitrate；The reaction dissolvent is the mixed solution of N,N-dimethylformamide and methyl alcohol.
Further, the mol ratio of the part and nickel salt is preferably (8~12):(25~35)；
The ratio of the part and N,N-dimethylformamide is 1mmol:(20~30) mL；
The mixed volume ratio of the N,N-dimethylformamide and methyl alcohol is 1:(2~4)；
The temperature of the reaction is 80~90 DEG C.
Technical scheme is clearly and completely described below in conjunction with the specific embodiment of the invention, it is clear that
Described embodiment is a part of embodiment of the invention, rather than whole embodiments.Those skilled in the art should manage
Solution, modifies to specific embodiment of the invention or some technical characteristics is replaced on an equal basis, without deviating from the present invention
The spirit of technical scheme, all should cover in the scope of protection of the invention.
Embodiment 1
(1) preparation of intermediate
A, 8- hydroxyls quinaldine (2- methyl -8-hydroxyquinoline) 1.25g and P-methoxybenzal-dehyde 1.2g is weighed in 50mL
Round-bottomed flask in, add the dissolving of 8mL acetic anhydrides, obtain mixed liquor；
B, the mixed liquor for obtaining step A carried out under the protection of nitrogen magnetic agitation, 90 DEG C be heated to reflux 18h；Then,
Reaction solution is poured into the frozen water of 700mL after being cooled to room temperature, is filtered when thering is solid to separate out, filtrate dichloromethane
Extraction three times, merges the organic phase obtained by three extractions；
C, the acetic acid washed away with distilled water in organic phase, then anhydrous sodium sulfate drying 4h is used, then organic phase concentrated under reduced pressure is obtained
To crude product；
D, with volume ratio be 1:9 petrol ether/ethyl acetate carries out silica gel column layer and is separated by decantation to 2.2g's as eluant, eluent
Intermediate, yield is 84%.Wherein, the intermediate is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8- acetoxyl group quinolines
Quinoline.
(2) preparation of part
A, the intermediate of 2g is dissolved in the flask equipped with 20mL pyridines and 20min is stirred, add the distilled water of 8mL simultaneously
Magnetic agitation is carried out, 22h is then heated to reflux；
After B, heating reflux reaction terminate, room temperature is cooled to, decompression boils off the pyridine in solution, then adds in reaction bulb
Enter 180mL distilled water, 25min is stirred at room temperature, filter to obtain solid, with distillation water washing solid, 1.58g is obtained after vacuum drying
Part, yield is 90%.Wherein, the part is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8-hydroxyquinoline.
(3) preparation of 8-hydroxyquinoline nickel complex
A, the part for taking 2.3mg are dissolved in the DMF of 0.2mL (DMF), are then delayed in the solution
It is slow that 0.9mL methanol solutions are added dropwise, then (the NO of Ni containing 5.5mg are added dropwise3)2DMF solution；Wherein, DMF:Methyl alcohol=1:2；
B, solution is placed in the sealed sample of 9mL bottle in, react 24h at 80 DEG C；
C, after thering are orange red bulk crystals to separate out, the crystal is washed with ethanol, be subsequently placed in 50 DEG C of baking oven and dry,
Product 2.12mg is obtained, yield is 84%.
(4) Structural Identification of the aggressiveness crystal of 8-hydroxyquinoline nickel complex six
The ir data of product is determined using FTIS, measurement result is as shown in figure 1, this is matched somebody with somebody
Characteristic waves (the cm of compound product-1) it is 3050,2930,2830,1620,1550,1500,1030,1280.
The crystal structure of the complex product is determined using German Brooker X single crystal diffractometers, as a result such as Fig. 2, monocrystalline X-
Ray diffraction data shows that the nickel complex that the present invention is prepared belongs to monoclinic system, and space group is C12/c1 (15), Z=
4,α=90 °,β=90.2130 (10),γ
=90 °,Elementary cell includes three central atom Ni (II) and six parts, Ni (II) atom
Hexa-coordinate mode is taken, an octahedra geometric configuration for distortion is formed, both sides central atom takes pentacoordinate mode, forms one
The tetragonal pyramid configuration of individual distortion.
Further to carrying out thermogravimetric analysis to complex product, its condition determination is：Under the protection of nitrogen, heating rate
It is 10 DEG C/min, measurement temperature scope is that between 30~1000 DEG C, Fig. 3 is the complex that the embodiment of the present invention 1 is prepared
Thermogravimetric analysis figure.As can be seen from Figure 3 nickel complex of the present invention just starts gradually to decompose to lose to match somebody with somebody at 370 DEG C or so
Body, shows the good thermal stability of the nickel complex.
Further research complex is in 2~300K temperature, the relation of magnetic susceptibility and temperature under 1000Oe field intensity, by right
The testing result of Fig. 4 is analyzed discovery, and the magnetic property of the complex observes Curie-Weiss law (Curie-
WeissLaw):1/χM=(T- θ)/C, wherein χMIt is molar susceptibility (emumol-1), θ is Weiss constant (K), and T is absolute
Temperature (K), C is Curie constant (emukmol-1).So, χM -1, T Curie-Weiss law formula be fitted, can obtain
To Curie constant C=12.58emukmol-1, Weiss constant θ=- 10.02K, by bear θ values can be coordinated with preliminary judgement
There is antiferromagnetic interaction between thing metal ion.
The present embodiment obtains a kind of with good anti-iron by will coordinate through the 8-hydroxyquinoline after alkyl modified and nickel
The complex of magnetic and heat endurance, the complex can be applied in production as antiferromagnet.Additionally, what the present invention was provided
Antiferromagnetic materials preparation method is simple, and raw material sources extensively, are capable of achieving large-scale production, before wide commercialization
Scape.
Embodiment 2
(1) preparation of intermediate
A, 8- hydroxyls quinaldine (2- methyl -8-hydroxyquinoline) 1.3g and P-methoxybenzal-dehyde 1.25g is weighed in 50mL
Round-bottomed flask in, add the dissolving of 9mL acetic anhydrides, obtain mixed liquor；
B, the mixed liquor for obtaining step A carried out under the protection of nitrogen magnetic agitation, 95 DEG C be heated to reflux 19h；Then,
Reaction solution is poured into the frozen water of 750mL after being cooled to room temperature, is filtered when thering is solid to separate out, filtrate dichloromethane
Extraction three times, merges the organic phase obtained by three extractions；
C, the acetic acid washed away with distilled water in organic phase, then anhydrous sodium sulfate drying 4.5h is used, then organic phase concentrated under reduced pressure
Obtain crude product；
D, with volume ratio be 1:9 petrol ether/ethyl acetate carries out silica gel column layer and is separated by decantation to 2.35g's as eluant, eluent
Intermediate, yield is 86%.Wherein, the intermediate is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8- acetoxyl group quinolines
Quinoline.
(2) preparation of part
A, the intermediate of 2.1g is dissolved in the flask equipped with 25mL pyridines and 25min is stirred, add the distillation of 10mL
Water simultaneously carries out magnetic agitation, is then heated to reflux 23h；
After B, heating reflux reaction terminate, room temperature is cooled to, decompression boils off the pyridine in solution, then adds in reaction bulb
Enter 200mL distilled water, 30min is stirred at room temperature, filter to obtain solid, with distillation water washing solid, 1.67g is obtained after vacuum drying
Part, yield is 91%.Wherein, the part is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8-hydroxyquinoline.
(3) preparation of 8-hydroxyquinoline nickel complex
A, the part for taking 2.5mg are dissolved in the DMF of 0.25mL (DMF), are then delayed in the solution
It is slow that 1mL methanol solutions are added dropwise, then (the NO of Ni containing 6mg are added dropwise3)2DMF solution；Wherein, DMF:Methyl alcohol=1:3.
B, solution is placed in the sealed sample of 10mL bottle in, react 24h at 85 DEG C；
C, after thering are orange red bulk crystals to separate out, the crystal is washed with ethanol, be subsequently placed in 55 DEG C of baking oven and dry,
Product 2.31mg is obtained, yield is 84%.
Embodiment 3
(1) preparation of intermediate
A, 8- hydroxyls quinaldine (2- methyl -8-hydroxyquinoline) 1.35g and P-methoxybenzal-dehyde 1.3g is weighed in 50mL
Round-bottomed flask in, add the dissolving of 10mL acetic anhydrides, obtain mixed liquor；
B, the mixed liquor for obtaining step A carried out under the protection of nitrogen magnetic agitation, 100 DEG C be heated to reflux 20h；Connect
, reaction solution is poured into the frozen water of 800mL after being cooled to room temperature, filtered when thering is solid to separate out, filtrate dichloro
Methane is extracted three times, merges the organic phase obtained by three extractions；
C, the acetic acid washed away with distilled water in organic phase, then anhydrous sodium sulfate drying 5h is used, then organic phase concentrated under reduced pressure is obtained
To crude product；
D, with volume ratio be 1:9 petrol ether/ethyl acetate carries out silica gel column layer and is separated by decantation to 2.51g's as eluant, eluent
Intermediate, yield is 88%.Wherein, the intermediate is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8- acetoxyl group quinolines
Quinoline.
(2) preparation of part
A, the intermediate of 2.2g is dissolved in the flask equipped with 30mL pyridines and 30min is stirred, add the distillation of 12mL
Water simultaneously carries out magnetic agitation, is then heated to reflux 24h；
After B, heating reflux reaction terminate, room temperature is cooled to, decompression boils off the pyridine in solution, then adds in reaction bulb
Enter 220mL distilled water, 35min is stirred at room temperature, filter to obtain solid, with distillation water washing solid, 1.77g is obtained after vacuum drying
Part, yield is 92%.Wherein, the part is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8-hydroxyquinoline.
(3) preparation of 8-hydroxyquinoline nickel complex
A, the part for taking 2.7mg are dissolved in the DMF of 0.3mL (DMF), are then delayed in the solution
It is slow that 1.1mL methanol solutions are added dropwise, then (the NO of Ni containing 7mg are added dropwise3)2DMF solution；Wherein, DMF:Methyl alcohol=1:4；
B, solution is placed in the sealed sample of 11mL bottle in, react 24h at 90 DEG C；
C, after thering are orange red bulk crystals to separate out, the crystal is washed with ethanol, be subsequently placed in 60 DEG C of baking oven and dry,
Product 2.52mg is obtained, yield is 85%.
The explanation of above example is only intended to help and understands the method for the present invention and its core concept.It should be pointed out that right
For those skilled in the art, under the premise without departing from the principles of the invention, the present invention can also be carried out
Some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (9)
1. a kind of 8-hydroxyquinoline nickel complex, with the structure as shown in formula I：
2. the preparation method of the 8-hydroxyquinoline nickel complex described in a kind of claim 1, including：
A) 8- hydroxyls quinaldine and P-methoxybenzal-dehyde are reacted in reaction dissolvent, is obtained reaction intermediate；
B) reaction intermediate for obtaining step a) reacts with pyridine, water successively, obtains part；
C) part and nickel salt for obtaining step b) are reacted in reaction dissolvent, are obtained the 8-hydroxyquinoline nickel and are coordinated
Thing.
3. preparation method according to claim 2, it is characterised in that reaction dissolvent described in step a) is acetic anhydride.
4. preparation method according to claim 2, it is characterised in that the condition reacted described in step a) is：In inertia
It is heated to reflux under the protection of gas；
The inert gas includes nitrogen, argon gas or helium；
The temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h.
5. preparation method according to claim 2, it is characterised in that in step b) after pyridine is added first heating stirring,
Then water is added to be heated at reflux.
6. preparation method according to claim 5, it is characterised in that the temperature of the heating stirring is 90~100 DEG C, when
Between be 20~30min；
The temperature being heated at reflux is 135~140 DEG C, and the time is 22~24h.
7. preparation method according to claim 2, it is characterised in that nickel salt includes described in step c)：Nickel nitrate, sulfuric acid
One or more in nickel, hydrochloric acid nickel and nickel phosphate；
The mol ratio of the part and nickel salt is (8~12):(25~35).
8. preparation method according to claim 2, it is characterised in that reaction dissolvent described in step c) is N, N- dimethyl
The mixed solution of formamide and methyl alcohol；
The ratio of the part and N,N-dimethylformamide is 1mmol:(20~30) mL；
The mixed volume ratio of the N,N-dimethylformamide and methyl alcohol is 1:(2~4).
9. preparation method according to claim 2, it is characterised in that the temperature reacted described in step c) is 80~90
℃。
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| CN113773350A (en) * | 2021-07-16 | 2021-12-10 | 云南电网有限责任公司电力科学研究院 | Metal complex hydrogen storage material and preparation method thereof |
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| CN104388080A (en) * | 2014-10-28 | 2015-03-04 | 广东工业大学 | Yellow-light electroluminescent material based on 8-hydroxyquinoline zinc metal complex tripolymer and controllable preparation method thereof |
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2017
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104388080A (en) * | 2014-10-28 | 2015-03-04 | 广东工业大学 | Yellow-light electroluminescent material based on 8-hydroxyquinoline zinc metal complex tripolymer and controllable preparation method thereof |
Non-Patent Citations (2)
| Title |
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| GUOZAN YUAN等: "Self-Assembly of Five 8-Hydroxyquinolinate-Based Complexes: Tunable Core,", 《CHEMISTRY – AN ASIAN JOURNAL》 * |
| 崔建中 等: "N,N′-双( 2- 吡啶乙基)二硫代草酰胺根桥联的异三核锰(II)铜(II)锰(II)、镍(II)铜(II)镍(II)和三核镍(II)配合物的合成及性质", 《无机化学学报》 * |
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| CN113773350A (en) * | 2021-07-16 | 2021-12-10 | 云南电网有限责任公司电力科学研究院 | Metal complex hydrogen storage material and preparation method thereof |
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