CN107501310A - Three core rare earth compoundings and its solvothermal preparation method and application based on schiff base ligand - Google Patents
Three core rare earth compoundings and its solvothermal preparation method and application based on schiff base ligand Download PDFInfo
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- CN107501310A CN107501310A CN201710798218.XA CN201710798218A CN107501310A CN 107501310 A CN107501310 A CN 107501310A CN 201710798218 A CN201710798218 A CN 201710798218A CN 107501310 A CN107501310 A CN 107501310A
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- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract description 49
- 239000002262 Schiff base Substances 0.000 title claims abstract description 41
- 150000004753 Schiff bases Chemical class 0.000 title claims abstract description 40
- 239000003446 ligand Substances 0.000 title claims abstract description 34
- 150000002910 rare earth metals Chemical class 0.000 title claims abstract description 30
- 238000013329 compounding Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- -1 rare earth ion Chemical class 0.000 claims abstract description 19
- 239000013078 crystal Substances 0.000 claims abstract description 8
- 241001478240 Coccus Species 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000000022 bacteriostatic agent Substances 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 229910052693 Europium Inorganic materials 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 claims description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 2
- MWFSXYMZCVAQCC-UHFFFAOYSA-N gadolinium(iii) nitrate Chemical compound [Gd+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O MWFSXYMZCVAQCC-UHFFFAOYSA-N 0.000 claims description 2
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- CFYGEIAZMVFFDE-UHFFFAOYSA-N neodymium(3+);trinitrate Chemical compound [Nd+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CFYGEIAZMVFFDE-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- YWECOPREQNXXBZ-UHFFFAOYSA-N praseodymium(3+);trinitrate Chemical compound [Pr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YWECOPREQNXXBZ-UHFFFAOYSA-N 0.000 claims description 2
- YJVUGDIORBKPLC-UHFFFAOYSA-N terbium(3+);trinitrate Chemical compound [Tb+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YJVUGDIORBKPLC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 abstract description 6
- 239000001301 oxygen Substances 0.000 abstract description 6
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract description 5
- 238000012916 structural analysis Methods 0.000 abstract description 3
- 230000001629 suppression Effects 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical class CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 14
- 229960005222 phenazone Drugs 0.000 description 9
- 241000222122 Candida albicans Species 0.000 description 5
- 230000002421 anti-septic effect Effects 0.000 description 5
- 229940095731 candida albicans Drugs 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910001428 transition metal ion Inorganic materials 0.000 description 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 241000040710 Chela Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000002815 broth microdilution Methods 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- USJZIUVMYSUNGB-UHFFFAOYSA-N neodymium;hydrate Chemical compound O.[Nd] USJZIUVMYSUNGB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The present invention provides a kind of three core rare earth compoundings and its solvothermal preparation method and application based on schiff base ligand, the schiff bases for respectively having the aromatic aldehyde of hydroxyl and 4 amino antipyrines to be formed using ortho position and meta is part, with rare earth ion in low temperature, the h of confined reaction 48~72 under the conditions of mixed organic solvents, it is clear and definite to form structure for coordination in enclosed high pressure environment, three stable core rare earth compoundings of property, from complex structure, two hydroxyl oxygens of aromatic aldehyde ortho position and meta are not only involved in being coordinated, oxygen bridge is also formed to link up three rare earth ions, improve the stability of complex.Its solvothermal preparation method is simple and easy to control, purifying is convenient, can quickly obtain complex crystal, be convenient for structural analysis and performance study；And antibacterial tests find the present invention the three core rare earth compoundings based on schiff base ligand have the function that it is anti-read coccus, can be applied as bacteriostatic agent suppression read on coccus.
Description
Technical field
The present invention relates to metal complex field, specifically a kind of three core rare earth compoundings based on schiff base ligand and its
Solvothermal preparation method and application.
Background technology
4- amino antipyrines are among widely used medicine, and 4- amino antipyrine derivatives are in antibacterial, antitumor
Etc. there is activity well, so the synthesis and research of 4- amino antipyrine derivatives are all the time as scientific worker
Study hotspot.Schiff bases is primarily referred to as containing imines or azomethine characteristic group（- RC=N-）A kind of organic compound, lead to
Often formed by ammonia and active carbonyl group condensation, there is unique bioactivity.4- amino antipyrines have good biological property
And coordination property, it can be reacted with some aromatic aldehydes, the schiff bases with C=N double bonds, such seat are formed using Aldehyde-ammonia Condensation
Husband's aar ligand has the N and O atom that can be coordinated with transition metal ions or rare earth ion, is easily formed stable chela
Compound, strengthen the bioactivity of complex.
But study at present it is more be all schiff bases and transition metal ions coordination, schiff bases and rare earth metal from
The yield that son forms complex is typically relatively low, and the synthetic method of complex is complicated, and known schiff bases and rare earth metal
The complex that ion is formed is mostly monokaryon or binuclear complex, and because yield is relatively low, it is difficult to purify, coordinate to labor
The structure of thing causes certain difficulty.
The content of the invention
The technical problems to be solved by the invention be to provide a kind of three core rare earth compoundings based on schiff base ligand and its
Solvothermal preparation method and application, respectively there are aromatic aldehyde and the formation of 4- amino antipyrine of a hydroxyl using ortho position and meta
Schiff base ligand is raw material, and the three core rare earth compoundings to form that structure is clear and definite, property is stable are coordinated with rare earth ion, from
Seen in compound structure, two hydroxyl oxygens of aromatic aldehyde ortho position and meta are not only involved in being coordinated, and also form oxygen bridge three rare earth gold
Category ion links up, and improves the stability of complex.Its solvothermal preparation method is simple and easy to control, purifying is convenient, can be fast
Speed obtains complex crystal, is convenient for structural analysis and performance study.
In order to solve the above-mentioned technical problem, the present invention provides a kind of three core rare earth compoundings based on schiff base ligand, tool
There is structural formula as follows：
Wherein Ar represents benzene or naphthalene；R represents hydrogen, halogen atom, the alkyl of 1~4 carbon atom, alkoxy, substitution alkyl or nitre
One kind in base；Ln3+Represent rare earth ion；Preferably, Ar be benzene, R be hydrogen, Ln3+For Nd3+。
From structure, the three core rare earth compoundings of the invention based on schiff base ligand are matched somebody with somebody with existing Schiff base rare-earth
Compound is compared, and is had following different：One of schiff bases of the three core rare earth compoundings based on schiff base ligand of the present invention
Part only ketonic oxygen participates in coordination, and ketonic oxygen, imines nitrogen and the hydroxyl oxygen of another schiff base ligand both participate in coordination, the 3rd
Schiff base ligand then only has two hydroxyl oxygens to participate in coordination, and these hydroxyl oxygens also form oxygen bridge in addition to participating in being coordinated
Three rare earth ions are linked up, improve the stability of complex；In complex formation, part schiff bases is also
Decomposed, one of catabolite 2, two hydroxyl oxygens and a ketonic oxygen of 3- aromatic dihydroxy aldehyde are also assisted in and matched somebody with somebody
Position.
The solvothermal preparation method of the three core rare earth compoundings based on schiff base ligand of the present invention, step are：By Schiff
Aar ligand, absolute ethyl alcohol, organic solvent and rare earth ion compound are placed in reaction bulb, are stirred at room temperature to solids dissolving simultaneously
It is well mixed, obtain mixed liquor；Mixed liquor is transferred in reactor, the compactedness for controlling reactor is 80%, and temperature is 60~90
DEG C, 48~72 h are reacted, then naturally cool to room temperature, carry out separation of solid and liquid, and washed at least 3 times with absolute ethyl alcohol, you can
Obtain the three core rare earth compounding crystal based on schiff base ligand；
The general structure of described schiff base ligand is：
Wherein Ar represents benzene or naphthalene；R represents hydrogen, halogen atom, the alkyl of 1~4 carbon atom, alkoxy, substitution alkyl or nitre
One kind in base.
Described rare earth ion compound is cerous nitrate, samaric nitrate, gadolinium nitrate, neodymium nitrate, praseodymium nitrate, lanthanum nitrate, nitric acid
One kind in europium or terbium nitrate；Described organic solvent is one in methanol, dichloromethane, acetonitrile, ethyl acetate, dimethyl sulfoxide
Kind or two or more any mixture.
The solvothermal preparation method of the present invention is simple to operate, and purifying is convenient, can quickly obtain complex crystal, can be compared with
Complex monocrystal is easily turned out, is convenient for structural analysis and performance study.
The three core rare earth compoundings based on schiff base ligand of the present invention are suppressing to read the application on coccus as bacteriostatic agent.
Candida albicans is most common conditioned pathogen in fungi, and it often parasitizes skin, oral cavity, vagina and intestinal mucosa of people etc., when
Human body immune function is low or the micro-ecological environment at position of normally living away from home is lacked of proper care, and easily causes candidiasis, therefore develops effective
Antifungal drug be all the time medical personal goal in research, three core rare earths of the invention based on schiff base ligand coordinate
Thing is shown to the good biocidal property of candida albicans as bacteriostatic agent.
Brief description of the drawings
Fig. 1 is the crystal structure figure of 2,3- 4-dihydroxy benzaldehyde contracting antipyrine rare earth Nd complex prepared by embodiment 2.
Fig. 2 is 2,3- 4-dihydroxy benzaldehyde contracting antipyrine rare earth Nd complex prepared by embodiment 2 to reading the suppression of coccus
Bacterium loop graph.
Embodiment
With reference to embodiment, the invention will be further described：
The preparation of the schiff base ligand of embodiment 1：
Equipped with agitator, temperature control device reactor in add 4-AA (0.4064 g, 2 mmol), anhydrous
The ml of ethanol 40, temperature control in 60~80 DEG C of stirring and dissolvings, be slowly added dropwise 2,3- 4-dihydroxy benzaldehydes (0.2762 g, 2
Mmol), reaction keeps well mixed, continues stirring more than 2 hours, temperature control filters at 60~80 DEG C and uses absolute ethyl alcohol
Washing reaction precipitates, and obtains light brown 2,3- 4-dihydroxy benzaldehyde contracting antipyrines, yield 88%.
The preparation of three core rare earth compoundings of the embodiment 2 based on schiff base ligand
By 0.06 gram of 2,3- 4-dihydroxy benzaldehyde contractings antipyrine, absolute ethyl alcohol 30mL, the mL of ethyl acetate 15, triethylamine 0.5mL
It is placed in the g of six nitric hydrate neodymium 0.08 in reaction bulb, the stirring of above-mentioned solution is mixed into fully dissolving at room temperature.Solution is put into
In 50 mL reactor inner bags, compactedness 80%, 48~36h of solvent thermal reaction is carried out at 60~90 DEG C, then natural cooling
To room temperature, red-brown powder crystalline solid is obtained.After separation of solid and liquid, washed 5 times with absolute ethyl alcohol, that is, obtain 2,3- dihydroxy benzenes first
Aldehyde contracting antipyrine rare earth neodymium complex crystal.
The crystal structure of 2,3- 4-dihydroxy benzaldehyde contracting antipyrine rare earth Nd complex is as shown in figure 1, its crystallography number
According to as shown in table 1.
The crystallographic data of the 2,3- 4-dihydroxy benzaldehyde contracting antipyrine rare earth Nd complex of table 1
The anti-microbial property test of three core rare earth compoundings of the embodiment 3 based on schiff base ligand and evaluation：
Test uses culture medium diffusion method, is constantly dissolved using antiseptic and forms various concentrations gradient through AGP test, with display
Its antibacterial action.
Operating procedure is：2,3- 4-dihydroxy benzaldehyde contracting antipyrine rare earth Nd complex is dissolved with DMSO, is configured to
0.001 mol/L solution, carry out the bacteriostatic test to reading coccus.Using culture medium diffusion method, passed through in 37 DEG C of incubators
After 18~24 h cultures, its antibacterial circle diameter is determined with slide measure.
Bacteriostatic experiment is issued according to Ministry of Health of the People's Republic of China 2002《Disinfection technology standard》Standard, to antibacterial
Performance test is represented using flat board filter paper enzyme, nutrient broth dilution method, culture medium diffusion method and vibration flask method, and reference
The issue of the National Development and Reform Commission of the People's Republic of China (PRC)《People's Republic of China's chemical industry standard：Inorganic antibacterial
Agent-performance and evaluation》, anti-microbial property is evaluated.In 121 DEG C of height before all articles for use uses of bacteriostatic test of the present invention
Temperature 15 min of sterilizing, and operated under superclean bench.
Inhibition zone result judges regulation and anti-microbial property evaluation criterion is：At least repeating experiment negative control group three times should nothing
Inhibition zone produces, and antiseptic sample has fungistatic effect, and it is qualified to be judged to；Otherwise it is invalid to test.Pass through antibacterial circle diameter size
To judge whether antiseptic has antibacterial ability.According to《People's Republic of China's chemical industry standard：Inorganic antiseptic performance and
Evaluation》, antibacterial circle diameter is less than or equal to 7 mm persons, is judged to no bacteriostasis；Antibacterial circle diameter is more than 7 mm persons, there is weak suppression
Bacterium acts on；Inhibition zone has moderate antibacterial effect in 10~20 mm persons；Antibacterial circle diameter is more than 20 mm persons, there is strong bacteriostasis.
Fig. 2 be three core rare earth compoundings based on schiff base ligand prepared by embodiment 2 to reading the antibacterial loop graph of coccus,
It is 2,3- 4-dihydroxy benzaldehyde contracting antipyrine rare earth Nd complex respectively to have 4 inhibition zones in Fig. 2, from result, 2,3-
4-dihydroxy benzaldehyde contracting antipyrine rare earth Nd complex to the antibacterial circle diameter average out to 26mm of candida albicans, complex it is antibacterial
Effect is obvious.Therefore, issued according to Ministry of Health of the People's Republic of China 2006《Disinfection technology standard》Standard, it is of the invention
The three core rare earth compoundings based on schiff base ligand have stronger bacteriostasis to candida albicans, belong to preferable antifungal agents, can
It is applied to antibacterial field as antiseptic.
Above-described embodiment is interpreted as being merely to illustrate the present invention rather than limited the scope of the invention.Reading
After the content of the invention recorded, those skilled in the art can make various changes or modifications to the present invention, these equivalent changes
Change and modification equally falls into the scope of the claims in the present invention.
Claims (7)
1. the three core rare earth compoundings based on schiff base ligand, it is characterized in that having following structural formula：
Wherein Ar represents benzene or naphthalene；R is represented in hydrogen, halogen, the alkyl of 1~4 carbon atom, alkoxy, substitution alkyl or nitro
One kind；Ln3+Represent rare earth ion.
2. the three core rare earth compoundings based on schiff base ligand as claimed in claim 1, it is characterised in that：Ar is benzene, and R is
Hydrogen, Ln3+For Nd3+。
3. the solvothermal preparation method of the three core rare earth compoundings based on schiff base ligand described in claim 1 or 2, its feature
It is, step is：
Schiff base ligand, absolute ethyl alcohol, organic solvent and rare earth ion compound are placed in reaction bulb, stirred at room temperature to solid
Body thing dissolves and is well mixed, and obtains mixed liquor；Mixed liquor is transferred in reactor, the compactedness for controlling reactor is 80%, temperature
Degree reacts 48~72 h, then naturally cools to room temperature at 60~90 DEG C, carries out separation of solid and liquid, and with absolute ethyl alcohol wash to
It is few 3 times, you can to obtain the three core rare earth compounding crystal based on schiff base ligand；
The structural formula of described schiff base ligand is：
Wherein Ar represents benzene or naphthalene；R represents one in halogen, the alkyl of 1~4 carbon atom, alkoxy, substitution alkyl or nitro
Kind.
4. the solvothermal preparation method of the three core rare earth compoundings according to claim 3 based on schiff base ligand, it is special
Sign is：Ar is benzene, and R is hydrogen.
5. the solvothermal preparation method of the three core rare earth compoundings based on schiff base ligand according to claim 3 or 4, its
It is characterised by：Described rare earth ion compound is cerous nitrate, samaric nitrate, gadolinium nitrate, neodymium nitrate, praseodymium nitrate, lanthanum nitrate, nitric acid
One kind in europium or terbium nitrate.
6. the solvothermal preparation method of the three core rare earth compoundings according to claim 3 based on schiff base ligand, it is special
Sign is：Described organic solvent is one kind or any two kinds in methanol, dichloromethane, acetonitrile, ethyl acetate, dimethyl sulfoxide
Or two or more mixture.
7. the three core rare earth compoundings based on schiff base ligand described in claim 1 or 2 are suppressing to read coccus as bacteriostatic agent
On application.
Priority Applications (1)
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| CN109796478A (en) * | 2019-01-10 | 2019-05-24 | 广西师范大学 | Monokaryon dysprosium complex based on double schiff base ligand and its preparation method and application |
| CN110970569A (en) * | 2018-09-29 | 2020-04-07 | Tcl集团股份有限公司 | Quantum dot light-emitting diode and preparation method thereof |
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