CN106810496B - A kind of 8-hydroxyquinoline nickel complex and preparation method thereof - Google Patents
A kind of 8-hydroxyquinoline nickel complex and preparation method thereof Download PDFInfo
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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 8 oxyquinoline nickel complexes of one kind and preparation method thereof.The present invention provides a kind of 8 oxyquinoline nickel complexes to have good anti-ferromagnetism, and good thermal stability with structure shown in formula (I), can be used as antiferromagnet applied in photoelectric properties study on regulation field.The present invention also provides the above-mentioned preparation methods with anti-ferromagnetic complex, and preparation process is simple, and raw material sources are extensively, it can be achieved that large-scale production, has wide Commercial Prospect.
Description
Technical field
The invention belongs to metal complex fields, 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 then provided more effectively for the design of crystal and crystal engineering applied to solid matter self assembly
Method, the design synthesis of coordination polymer are the new approach that crystal engineering provides for the design of novel supramolecular structure.
The structure of substance determines that the physicochemical properties and performance of substance, physicochemical properties and performance are the reflections of the structure of matter, only
There is the structure for fully understanding substance, the performance of substance could deeply be appreciated and understood, 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
Prediction becomes the emphasis of crystal engineering research.
Coordination polymer because of its special structure, and absorption with detach, be catalyzed, molecule and ion exchange, molecule magnetic
Property, shining has potential application with non-linear etc., just more and more paid attention to, therefore design and synthesize newly
The coordination polymer of type has become a hot spot.8-hydroxyquinoline ligand is a flexible and changeable ligand, has a variety of match
Position mode, can form stable complex with transition metal or rare earth ion.It is proposed from Kodak Company by 8-hydroxyquinoline
After aluminium is used as the emitting layer material in electroluminescent device, this kind of molecule is constantly subjected to organic electroluminescence device academia and work
The extensive attention of industry.In addition, people also attempt to introduce functional group by the different parts in 8-hydroxyquinoline, then pass through
It is coordinated to obtain the metal complex of different function with different metal, Ghosh etc. has found that 8-hydroxyquinoline class complex can be potential
Treatment applied to Parkinson disease.Therefore, the different work(obtained using 8-hydroxyquinoline class compound as ligand are furtherd investigate
The metal complex of energy can not only provide more more novel structural models in field of coordinative chemistry for us, more can be in optics
The many aspects such as element exploitation, bionics techniques, biologic inorganic and drug development play a role.
Invention content
In view of this, the present invention provides a kind of 8-hydroxyquinoline nickel complex and preparation method thereof, it is provided by the present invention
8-hydroxyquinoline nickel complex have good anti-ferromagnetism and thermal stability.
The specific technical solution of the present invention is as follows：
The present invention provides a kind of 8-hydroxyquinoline nickel complexes, have the structure as shown in formula I：
The present invention also provides a kind of preparation methods of above-mentioned 8-hydroxyquinoline nickel complex, including：
A) 8- hydroxyls quinaldine and P-methoxybenzal-dehyde are reacted in reaction dissolvent, obtains reaction intermediate；
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand；
C) the obtained ligands of step b) and nickel salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline nickel and matches
Close object.
Preferably, reaction dissolvent described in step a) is acetic anhydride.
Preferably, the condition reacted described in step a) is：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 be 135~140 DEG C, the time be 22~for 24 hours.
Preferably, nickel salt described in step c) includes：Nickel nitrate, nickel sulfate, hydrochloric acid nickel and one kind or more in nickel phosphate
Kind；
The molar ratio of the ligand and nickel salt is (8~12):(25~35).
Preferably, reaction dissolvent described in step c) is the mixed solution of n,N-Dimethylformamide and methanol；
The ratio of the ligand and N,N-dimethylformamide is 1mmol:(20~30) mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is 1:(2~4).
Preferably, the temperature reacted described in step c) is 80~90 DEG C.
The present invention provides a kind of 8-hydroxyquinoline nickel complexes to have good anti-iron with structure shown in formula (I)
Magnetism, and good thermal stability can be used as antiferromagnet applied in photoelectric properties study on regulation field.The present invention also provides
The above-mentioned preparation method with anti-ferromagnetic complex, preparation process is simple, and raw material sources are extensively, it can be achieved that large-scale
Production has wide Commercial Prospect.
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
The embodiment of invention for those of ordinary skill in the art without creative efforts, can also basis
The attached drawing of offer obtains other attached drawings.
Fig. 1 is the infrared spectrogram of the 8-hydroxyquinoline nickel complex obtained in embodiment 1；
Fig. 2 is the crystal structure figure of the 8-hydroxyquinoline nickel complex obtained in embodiment 1；
Fig. 3 is the thermogravimetric analysis figure of the 8-hydroxyquinoline nickel complex obtained in embodiment 1；
Fig. 4 is the magnetic detection figure of the 8-hydroxyquinoline nickel complex obtained in embodiment 1.
Specific implementation mode
The present invention provides a kind of 8-hydroxyquinoline nickel complexes, have 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 °,
The present invention also provides a kind of preparation methods of above-mentioned 8-hydroxyquinoline nickel complex, including：
A) 8- hydroxyls quinaldine and P-methoxybenzal-dehyde are reacted in reaction dissolvent, obtain 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 involved in step a) is as follows：
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand, the chemical name of the ligand
For (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8-hydroxyquinoline；
Wherein, the reaction equation involved in step b) is as follows：
C) the obtained ligands of step b) and nickel salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline nickel and matches
Object is closed, molecular formula is：C108H78F6N6O12Ni3；
Wherein, the reaction equation involved 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 additive amount of 8- hydroxyls quinaldine is 1.25~1.35g, and the additive amount 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 be 135~140 DEG C, the time be 22~for 24 hours.
In the present invention, nickel salt described in step c) is preferably one kind in nickel nitrate, nickel sulfate, hydrochloric acid nickel and nickel phosphate
Or a variety of, more preferably nickel nitrate；The reaction dissolvent is the mixed solution of N,N-dimethylformamide and methanol.
Further, the molar ratio of the ligand and nickel salt is preferably (8~12):(25~35)；
The ratio of the ligand and N,N-dimethylformamide is 1mmol:(20~30) mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is 1:(2~4)；
The temperature of the reaction is 80~90 DEG C.
Technical scheme of the present invention 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 the embodiment of the present invention, instead of all the embodiments.Those skilled in the art should manage
Solution, modifies to specific embodiments of the present invention or is replaced on an equal basis to some technical characteristics, without departing from the present invention
The spirit of technical solution should all 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, be added 8mL acetic anhydrides dissolving, obtain mixed liquor；
B, by the mixed liquor that step A is obtained carried out under the protection of nitrogen magnetic agitation, 90 DEG C be heated to reflux 18h；Then,
Reaction solution is poured into the ice water of 700mL after being cooled to room temperature, is filtered when having solid precipitation, filtrate dichloromethane
Extraction three times, merges the organic phase of extraction gained three times；
C, the acetic acid in organic phase is washed away with distilled water, then 4h is dried with anhydrous sodium sulfate, then organic phase is concentrated under reduced pressure and obtains
To crude product；
D, it is 1 with volume ratio:9 petrol ether/ethyl acetate carries out silica gel column layer as eluant, eluent and is separated by decantation to 2.2g's
Intermediate, yield 84%.Wherein, which is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8- acetoxyl group quinolines
Quinoline.
(2) preparation of ligand
A, the intermediate of 2g is dissolved in the flask equipped with 20mL pyridines and is stirred 20min, add the distilled water of 8mL simultaneously
Magnetic agitation is carried out, 22h is then heated to reflux；
B, it after heating reflux reaction, is cooled to room temperature, decompression boils off the pyridine in solution, then adds into reaction bulb
Enter 180mL distilled water, stir 25min at room temperature, filter to obtain solid, is washed with distilled water solid, 1.58g is obtained after vacuum drying
Ligand, yield 90%.Wherein, which is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8-hydroxyquinoline.
(3) preparation of 8-hydroxyquinoline nickel complex
A, it takes the ligand of 2.3mg to be dissolved in the n,N-Dimethylformamide (DMF) of 0.2mL, then delays into 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:Methanol=1:2；
B, solution is placed in the sealed sample bottle of 9mL, is reacted for 24 hours at 80 DEG C；
C, after there are orange red bulk crystals to be precipitated, the crystal is washed with ethyl alcohol, is subsequently placed in 50 DEG C of baking oven and dries,
Obtain product 2.12mg, yield 84%.
(4) Structural Identification of six aggressiveness crystal of 8-hydroxyquinoline nickel complex
The ir data of product is measured using Fourier Transform Infrared Spectrometer, measurement result is as shown in Figure 1, this is matched
Close the characteristic waves (cm of object product-1) it is 3050,2930,2830,1620,1550,1500,1030,1280.
The crystal structure of the complex product is measured 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 °,Basic unit includes three central atom Ni (II) and six ligands, Ni (II) atom
Hexa-coordinate mode is taken, the octahedra geometric configuration of a distortion is formed, both sides central atom takes pentacoordinate mode, forms one
The tetragonal pyramid configuration of a distortion.
Further to carrying out thermogravimetric analysis to complex product, determination condition is：Under the protection of nitrogen, heating rate
For 10 DEG C/min, for measuring temperature ranging 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 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 relationship of magnetic susceptibility and temperature under 1000Oe field strength, by right
The testing result of Fig. 4 carries out analysis and finds, the magnetic property of the complex abides by Curie-Weiss law (Curie-
WeissLaw):1/χM=(T- θ)/C, wherein χMFor molar susceptibility (emumol-1), θ is Weiss constant (K), and T is absolute
Temperature (K), C are Curie constant (emukmol-1).So, χM -1, T be fitted with Curie-Weiss law formula, can obtain
To Curie constant C=12.58emukmol-1, Weiss constant θ=- 10.02K can be coordinated by negative θ values with preliminary judgement
There are antiferromagnetic interactions between object metal ion.
The present embodiment is obtained a kind of with good anti-iron by will coordinate with nickel through the 8-hydroxyquinoline after alkyl modified
Magnetic and thermal stability complex, the complex can be used as antiferromagnet and be applied in production.In addition, provided by the invention
Antiferromagnetic materials preparation method is simple, and raw material sources are extensively, it can be achieved that large-scale produce, before having 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, be added 9mL acetic anhydrides dissolving, obtain mixed liquor；
B, by the mixed liquor that step A is obtained carried out under the protection of nitrogen magnetic agitation, 95 DEG C be heated to reflux 19h；Then,
Reaction solution is poured into the ice water of 750mL after being cooled to room temperature, is filtered when having solid precipitation, filtrate dichloromethane
Extraction three times, merges the organic phase of extraction gained three times；
C, the acetic acid in organic phase is washed away with distilled water, then 4.5h is dried with anhydrous sodium sulfate, then organic phase is concentrated under reduced pressure
Obtain crude product；
D, it is 1 with volume ratio:9 petrol ether/ethyl acetate carries out silica gel column layer as eluant, eluent and is separated by decantation to 2.35g's
Intermediate, yield 86%.Wherein, which is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8- acetoxyl group quinolines
Quinoline.
(2) preparation of ligand
A, the intermediate of 2.1g is dissolved in the flask equipped with 25mL pyridines and is stirred 25min, add the distillation of 10mL
Water simultaneously carries out magnetic agitation, is then heated to reflux 23h；
B, it after heating reflux reaction, is cooled to room temperature, decompression boils off the pyridine in solution, then adds into reaction bulb
Enter 200mL distilled water, stir 30min at room temperature, filter to obtain solid, is washed with distilled water solid, 1.67g is obtained after vacuum drying
Ligand, yield 91%.Wherein, which is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8-hydroxyquinoline.
(3) preparation of 8-hydroxyquinoline nickel complex
A, it takes the ligand of 2.5mg to be dissolved in the n,N-Dimethylformamide (DMF) of 0.25mL, then delays into 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:Methanol=1:3.
B, solution is placed in the sealed sample bottle of 10mL, is reacted for 24 hours at 85 DEG C；
C, after there are orange red bulk crystals to be precipitated, the crystal is washed with ethyl alcohol, is subsequently placed in 55 DEG C of baking oven and dries,
Obtain product 2.31mg, yield 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, be added 10mL acetic anhydrides dissolving, obtain mixed liquor；
B, by the mixed liquor that step A is obtained carried out under the protection of nitrogen magnetic agitation, 100 DEG C be heated to reflux 20h；It connects
It, reaction solution is poured into the ice water of 800mL after being cooled to room temperature, be filtered when having solid precipitation, filtrate dichloro
Methane extracts the organic phase for merging extraction gained three times three times；
C, the acetic acid in organic phase is washed away with distilled water, then 5h is dried with anhydrous sodium sulfate, then organic phase is concentrated under reduced pressure and obtains
To crude product；
D, it is 1 with volume ratio:9 petrol ether/ethyl acetate carries out silica gel column layer as eluant, eluent and is separated by decantation to 2.51g's
Intermediate, yield 88%.Wherein, which is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8- acetoxyl group quinolines
Quinoline.
(2) preparation of ligand
A, the intermediate of 2.2g is dissolved in the flask equipped with 30mL pyridines and is stirred 30min, add the distillation of 12mL
Water simultaneously carries out magnetic agitation, is then heated to reflux for 24 hours；
B, it after heating reflux reaction, is cooled to room temperature, decompression boils off the pyridine in solution, then adds into reaction bulb
Enter 220mL distilled water, stir 35min at room temperature, filter to obtain solid, is washed with distilled water solid, 1.77g is obtained after vacuum drying
Ligand, yield 92%.Wherein, which is (E) -2- [the fluoro- 4- ethoxyl phenenyls vinyl of 2-] -8-hydroxyquinoline.
(3) preparation of 8-hydroxyquinoline nickel complex
A, it takes the ligand of 2.7mg to be dissolved in the n,N-Dimethylformamide (DMF) of 0.3mL, then delays into 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:Methanol=1:4；
B, solution is placed in the sealed sample bottle of 11mL, is reacted for 24 hours at 90 DEG C；
C, after there are orange red bulk crystals to be precipitated, the crystal is washed with ethyl alcohol, is subsequently placed in 60 DEG C of baking oven and dries,
Obtain product 2.52mg, yield 85%.
The explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvement and modification are also fallen within the protection scope of the claims of the present invention.
Claims (9)
1. a kind of 8-hydroxyquinoline nickel complex has the structure as shown in formula I：
2. a kind of preparation method of 8-hydroxyquinoline nickel complex described in claim 1, including：
A) 8- hydroxyls quinaldine and the fluoro- 4-methoxybenzaldehydes of 2- are reacted in reaction dissolvent, obtains reaction intermediate；
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand；
C) the obtained ligands of step b) and nickel salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline nickel cooperation
Object.
3. preparation method according to claim 2, which is characterized in that reaction dissolvent described in step a) is acetic anhydride.
4. preparation method according to claim 2, which is characterized 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 is 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, which is characterized 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, which is characterized in that the temperature of the heating stirring is 90~100 DEG C, when
Between be 20~30min；
The temperature being heated at reflux be 135~140 DEG C, the time be 22~for 24 hours.
7. preparation method according to claim 2, which is characterized in that nickel salt is described in step c)：Nickel nitrate, sulfuric acid
It is one or more in nickel, hydrochloric acid nickel and nickel phosphate；
The molar ratio of the ligand and nickel salt is (8~12):(25~35).
8. preparation method according to claim 2, which is characterized in that reaction dissolvent described in step c) is N, N- dimethyl
The mixed solution of formamide and methanol；
The ratio of the ligand and N,N-dimethylformamide is 1mmol:(20~30) mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is 1:(2~4).
9. preparation method according to claim 2, which is characterized in that the temperature reacted described in step c) is 80~90
℃。
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