CN108586501A - A kind of Zn complex and the preparation method and application thereof - Google Patents
A kind of Zn complex and the preparation method and application thereof Download PDFInfo
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- CN108586501A CN108586501A CN201810731285.4A CN201810731285A CN108586501A CN 108586501 A CN108586501 A CN 108586501A CN 201810731285 A CN201810731285 A CN 201810731285A CN 108586501 A CN108586501 A CN 108586501A
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- complex
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- acetone
- theophylline
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000011701 zinc Substances 0.000 claims abstract description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 32
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 32
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000523 sample Substances 0.000 claims abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 11
- 229960000278 theophylline Drugs 0.000 claims abstract description 9
- 230000005595 deprotonation Effects 0.000 claims abstract description 8
- 238000010537 deprotonation reaction Methods 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 230000003068 static effect Effects 0.000 claims abstract description 5
- 239000013078 crystal Substances 0.000 claims description 11
- 230000005284 excitation Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 2
- IJRVLVIFMRWJRQ-UHFFFAOYSA-N nitric acid zinc Chemical compound [Zn].O[N+]([O-])=O IJRVLVIFMRWJRQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000470 constituent Substances 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 6
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 abstract description 6
- 230000002349 favourable effect Effects 0.000 abstract description 4
- 238000010586 diagram Methods 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical class CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZSDJVGXBJDDOCD-UHFFFAOYSA-N benzene dioctyl benzene-1,2-dicarboxylate Chemical compound C(C=1C(C(=O)OCCCCCCCC)=CC=CC1)(=O)OCCCCCCCC.C1=CC=CC=C1 ZSDJVGXBJDDOCD-UHFFFAOYSA-N 0.000 description 1
- 238000012926 crystallographic analysis Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical class CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a kind of Zn complex and the preparation method and application thereof, the chemical structural formula of the Zn complex is [Zn2(C7H6N4O2)(C8H4O4) (OH) (DMF)] DMF, wherein C7H6N4O2For the theophylline of deprotonation, C8H4O4For the terephthalic acid (TPA) of deprotonation, DMF N, N dimethylformamides.Terephthalic acid (TPA), sodium hydroxide, theophylline are mixed with zinc nitrate, and are added to N, in the aqueous solution of N dimethylformamides, is stirred 10 minutes, static 72h in 95 DEG C of baking oven is subsequently placed in, the Zn complex is obtained after cooling.The Zn complex is used as the fluorescence probe of identification acetone.Not only preparation process is simple, chemical constituent is easily controllable by the present invention, favorable repeatability, yield are high, but also has very high sensitivity and selectivity to acetone, can be used as the fluorescence probe of highly sensitive, highly selective identification acetone.
Description
Technical field
The present invention relates to fluorescent probe technique fields more particularly to a kind of Zn complex and the preparation method and application thereof.
Background technology
Fluorescence probe is using fluorescent material as indicator, and it is glimmering to generate indicator under the excitation of certain wavelength light
Light realizes the qualitative or quantitative analysis to tested substance by fluorescence caused by detection.With traditional determination method
It compares, fluorescence probe has many advantages, such as that selectivity is good, sensitivity is good, instrument is simple, easy to operate, therefore in environment measuring, life
The fields extensive use such as object chemistry.In the prior art, the fluorescence probe material sensitivity of small molecule is relatively low for identification, selects
Property it is poor, and preparation process is complicated, chemical constituent is unable to control, poor repeatability.
Invention content
Fluorescence probe material sensitivity in order to solve in the prior art small molecule for identification is relatively low, selective poor,
And the technical problems such as preparation process is complicated, chemical constituent is unable to control, poor repeatability, low output, the present invention provides one kind
Zn complex and the preparation method and application thereof, not only preparation process is simple, chemical constituent is easily controllable, favorable repeatability, yield
Height, and there is very high sensitivity and selectivity to acetone, it can be used as the fluorescence of highly sensitive, highly selective identification acetone
Probe.
The purpose of the present invention is what is be achieved through the following technical solutions:
A kind of Zn complex, chemical formula C21H26N6O9Zn2, molecular weight 637.26, chemical structural formula is [Zn2
(C7H6N4O2)(C8H4O4) (OH) (DMF)] DMF, wherein C7H6N4O2For the theophylline of deprotonation, C8H4O4It is deprotonation to benzene
Dioctyl phthalate, DMF are n,N-Dimethylformamide;The structure of its minimum asymmetric cell is:
The crystal structural data of the Zn complex is as shown in following table one:
Table one
A kind of preparation method of Zn complex, including:Terephthalic acid (TPA), sodium hydroxide, theophylline are mixed with zinc nitrate, and
It is added in the aqueous solution of n,N-Dimethylformamide, stirs 10 minutes, be subsequently placed in static 72h in 95 DEG C of baking oven, it is cooling
Obtain above-mentioned Zn complex afterwards;The Zn complex is colourless bulk crystals;Wherein, the proportionate relationship of each raw material is such as
Under:
Preferably, the structure of the Zn complex is measured using single crystal diffractometer, the Zn complex is 305nm in wavelength
Incident light excitation under, launch blue-fluorescence.
Zn complex described in above-mentioned technical proposal is used as the fluorescence probe of identification acetone.
As seen from the above technical solution provided by the invention, Zn complex provided by the invention is by zinc, deprotonation
The elements such as theophylline, the terephthalic acid (TPA) of deprotonation, n,N-Dimethylformamide or group are constituted, can be in numerous organic solvents
Good recognition effect is obtained to acetone, therefore the Zn complex can be used as the fluorescence probe of identification acetone well.The present invention
Not only preparation process is simple, chemical constituent is easily controllable, favorable repeatability, yield are high, but also has to acetone very high sensitive
Degree and selectivity can be used as the fluorescence probe of highly sensitive, highly selective identification acetone.
Description of the drawings
In order to illustrate the technical solution of the embodiments of the present invention more clearly, required use in being described below to embodiment
Attached drawing be briefly described, it should be apparent that, drawings in the following description are only some embodiments of the invention, for this
For the those of ordinary skill in field, without creative efforts, other are can also be obtained according to these attached drawings
Attached drawing.
Fig. 1 is the minimum asymmetric cell schematic diagram of the Zn complex obtained by the embodiment of the present invention 1.
Fig. 2 is the fluorescence spectrum schematic diagram of the Zn complex obtained by the embodiment of the present invention 2.
Fig. 3 is fluorescence property detection signal of the Zn complex made from the embodiment of the present invention 2 in different solvents small molecule
Figure.
Fig. 4 is fluorescence intensity schematic diagram of the Zn complex in different solvents small molecule made from the embodiment of the present invention 2.
Specific implementation mode
With reference to the attached drawing in the embodiment of the present invention, technical solution in the embodiment of the present invention carries out clear, complete
Ground describes, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based on this
The embodiment of invention, every other implementation obtained by those of ordinary skill in the art without making creative efforts
Example, belongs to protection scope of the present invention.
Zn complex provided by the present invention and the preparation method and application thereof is described in detail below.The present invention is implemented
The content not being described in detail in example belongs to the prior art well known to professional and technical personnel in the field.
Embodiment 1
A kind of Zn complex, preparation method include:By 0.033g terephthalic acid (TPA)s, 0.020g sodium hydroxides, 0.025g
Theophylline is mixed with 0.035g zinc nitrates, and is added in the aqueous solution of 50mL n,N-Dimethylformamide, stirring 10 minutes, so
It is placed on static 72h in 95 DEG C of baking oven, the Zn complex in colourless bulk crystals is obtained after cooling.
Specifically, select size for 0.25 × 0.24 × 0.23mm3The embodiment of the present invention 1 obtained by Zn complex into
Row ray crystallographic analysis, single crystal diffraction data are collected using Bruker-AXS SMART APEX2 CCD diffractometers, use stone
The Mok alpha rays of black monochromator monochromatization2.69 °≤θ≤28.27 °, to obtain following result:This
Zn complex obtained by inventive embodiments 1 belongs to monoclinic system, and space group is all P21C, cell parameter are aboutα=90 °, β=109.718 °, γ=90 °.It is soft using Diamond
Part draws the crystal structure of the Zn complex, obtains minimum asymmetric cell schematic diagram as shown in Figure 1.
Embodiment 2
A kind of Zn complex, preparation method include:By 0.33g terephthalic acid (TPA)s, 0.20g sodium hydroxides, 0.25g theophylline
It mixes, and is added in the aqueous solution of 50mL n,N-Dimethylformamide with 0.35g zinc nitrates, stir 10 minutes, be subsequently placed in
Static 72h in 95 DEG C of baking oven obtains the Zn complex in colourless bulk crystals after cooling.
Specifically, following performance test is carried out to the Zn complex obtained by the embodiment of the present invention 2:
(1) single crystal diffractometer is used to carry out fluorometric investigation, incident light wave to the Zn complex obtained by the embodiment of the present invention 2
A length of 305nm, so as to obtain fluorescence spectrum schematic diagram as shown in Figure 2;In fig. 2, abscissa be wavenumber (i.e.
For wavelength, unit nm), ordinate is intensity (being intensity).As seen from Figure 2:2 institute of the embodiment of the present invention
Zn complex obtained launches blue-fluorescence under the incident light excitation that wavelength is 305nm.
(2) preparing nine kinds of liquid small molecules respectively (is respectively:Acetone, n,N-Dimethylformamide, N, N- dimethylacetamides
Amine, N, N- diethyl acetamides, ethyl alcohol, methanol, methyl pyrrolidone, acetonitrile, ethyl acetate) it is used as prepare liquid.Take this nine kinds
Each 3mL of liquid small molecule is added separately in nine 10mL reaction bulbs, then is separately added into the 3mg present invention in fact into nine reaction bulbs
The Zn complex obtained by example 2 is applied, and is ultrasonically treated 3~4 minutes, the Zn complex is made to be uniformly dispersed in prepare liquid, then
Consistent λ ex=305nm are tested as excitation wavelength using with solid fluorescence, and slit width is 1.5nm, tests this nine
The Fluorescence behaviour of Zn complex in reaction bulb, to obtain the detection of the fluorescence property in different solvents small molecule as shown in Figure 3
Schematic diagram (its abscissa indicates that wavelength, ordinate indicate relative intensity) and fluorescence intensity schematic diagram as shown in Figure 4.By Fig. 3
With Fig. 4 it can be seen that:The fluorescent quenching for only containing Zn complex in the reaction bulb of acetone is apparent, it is seen that the embodiment of the present invention 2
Obtained Zn complex can be used as the fluorescence probe of specific recognition acetone.
To sum up, the embodiment of the present invention not only preparation process is simple, chemical constituent is easily controllable, favorable repeatability, production
Amount is high, and has very high sensitivity and selectivity to acetone, can be used as the glimmering of highly sensitive, highly selective identification acetone
Light probe.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Any one skilled in the art is in the technical scope of present disclosure, the change or replacement that can be readily occurred in,
It should be covered by the protection scope of the present invention.Therefore, protection scope of the present invention should be with the protection model of claims
Subject to enclosing.
Claims (6)
1. a kind of Zn complex, which is characterized in that its chemical structural formula is [Zn2(C7H6N4O2)(C8H4O4)(OH)(DMF)]·
DMF, wherein C7H6N4O2For the theophylline of deprotonation, C8H4O4For the terephthalic acid (TPA) of deprotonation, DMF N, N- dimethyl formyls
Amine.
2. Zn complex according to claim 1, which is characterized in that the crystal structural data of Zn complex such as one institute of following table
Show:
Table one
3. a kind of preparation method of Zn complex, which is characterized in that including:By terephthalic acid (TPA), sodium hydroxide, theophylline and nitric acid
Zinc mixes, and is added in the aqueous solution of n,N-Dimethylformamide, stirs 10 minutes, is subsequently placed in static in 95 DEG C of baking oven
72h obtains the Zn complex described in any one of the claims 1 to 2 after cooling;
Wherein, the proportionate relationship of each raw material is as follows:
4. the preparation method of Zn complex according to claim 3, which is characterized in that the Zn complex is colourless
Bulk crystals.
5. the preparation method of Zn complex according to claim 3 or 4, which is characterized in that using single crystal diffractometer to institute
It states Zn complex to be measured, the Zn complex launches blue-fluorescence under the incident light excitation that wavelength is 305nm.
6. a kind of application of Zn complex, which is characterized in that by the Zn complex described in any one of the claims 1 to 2
Identify the fluorescence probe of acetone.
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CN201810731285.4A CN108586501A (en) | 2018-07-05 | 2018-07-05 | A kind of Zn complex and the preparation method and application thereof |
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CN201810731285.4A CN108586501A (en) | 2018-07-05 | 2018-07-05 | A kind of Zn complex and the preparation method and application thereof |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109251214A (en) * | 2018-11-29 | 2019-01-22 | 衡水学院 | A kind of Zn complex and its preparation method and application |
CN115287060A (en) * | 2022-03-24 | 2022-11-04 | 辽宁科技大学 | Blue light carbon dot, fluorescent powder, white light emitting diode and preparation method thereof |
Citations (3)
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CN104718214A (en) * | 2012-05-31 | 2015-06-17 | 国立科学研究中心 | Improved organic-inorganic hybrid solid having a modified outer surface |
CN105026854A (en) * | 2012-08-15 | 2015-11-04 | 阿科玛股份有限公司 | Adsorption systems using metal-organic frameworks |
CN107573367A (en) * | 2017-08-17 | 2018-01-12 | 北京石油化工学院 | A kind of Zn complex and preparation method and application |
-
2018
- 2018-07-05 CN CN201810731285.4A patent/CN108586501A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104718214A (en) * | 2012-05-31 | 2015-06-17 | 国立科学研究中心 | Improved organic-inorganic hybrid solid having a modified outer surface |
CN105026854A (en) * | 2012-08-15 | 2015-11-04 | 阿科玛股份有限公司 | Adsorption systems using metal-organic frameworks |
CN107573367A (en) * | 2017-08-17 | 2018-01-12 | 北京石油化工学院 | A kind of Zn complex and preparation method and application |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109251214A (en) * | 2018-11-29 | 2019-01-22 | 衡水学院 | A kind of Zn complex and its preparation method and application |
CN115287060A (en) * | 2022-03-24 | 2022-11-04 | 辽宁科技大学 | Blue light carbon dot, fluorescent powder, white light emitting diode and preparation method thereof |
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