CN109400634A - The application of 2,5- dihydric para-phthalic acid's indium complex and preparation method thereof and fluorescence detection hydrazine hydrate - Google Patents
The application of 2,5- dihydric para-phthalic acid's indium complex and preparation method thereof and fluorescence detection hydrazine hydrate Download PDFInfo
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- CN109400634A CN109400634A CN201811454642.3A CN201811454642A CN109400634A CN 109400634 A CN109400634 A CN 109400634A CN 201811454642 A CN201811454642 A CN 201811454642A CN 109400634 A CN109400634 A CN 109400634A
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- indium
- hydrazine hydrate
- phthalic acid
- dihydric para
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 title claims abstract description 27
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 title claims abstract description 25
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 23
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 229910052738 indium Inorganic materials 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000001917 fluorescence detection Methods 0.000 title claims abstract description 7
- 238000010668 complexation reaction Methods 0.000 title abstract description 3
- OYFRNYNHAZOYNF-UHFFFAOYSA-N H2dhybdc Natural products OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 2,5-Dihydroxyterephthalic acid indium Chemical compound 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 229910001449 indium ion Inorganic materials 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 18
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000908 ammonium hydroxide Substances 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 3
- 230000000171 quenching effect Effects 0.000 abstract description 3
- 238000001514 detection method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012621 metal-organic framework Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 230000007670 carcinogenicity Effects 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- DYFUIGSYDAHRLA-UHFFFAOYSA-N formic acid;indium Chemical compound [In].OC=O DYFUIGSYDAHRLA-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
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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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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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- 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
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- 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
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- 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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Abstract
The invention discloses the application of a kind of 2,5-Dihydroxyterephthalic acid indium complex and preparation method thereof and fluorescence detection hydrazine, the structural unit of the complex is In2(DOBDC)2(OH)2, indium ion is positive trivalent in formula, and DOBDC represents the 2,5-Dihydroxyterephthalic acid dianion for losing hydrogen atom on two carboxyls, and hydroxyl is negative monovalence.The present invention is with 2,5- dihydric para-phthalic acid is ligand, indium complex is prepared into using solvent-thermal method, it is with fluorescence property, and there can be good Fluorescence quenching effect to hydrazine hydrate, and to ammonium hydroxide and azanol without response, it can be used as fluorescent optical sensor to detect hydrazine hydrate, while excluding the interference of ammonium hydroxide and azanol.
Description
Technical field
The invention belongs to indium-aromatic carboxylic acids metal organic complex technical fields, and in particular to a kind of pair of hydrazine hydrate tool
There are the 2,5-Dihydroxyterephthalic acid indium complex of fluorescence response and the preparation method of the complex.
Background technique
In recent years, metal-organic functions complex because its with gas storage, molecular recognition, ion exchange, selectivity urge
The functions such as change, gas absorption and fluorescence response, and become the hot spot of vast researcher concern.Match in metal-organic functions
It closes in object, indium Base Metal-organic functions complex is by its unique structure feature, topological structure abundant and in many necks
The wide application prospect in domain has become a part indispensable in metal-organic framework materials family, receives researcher
Extensive concern, simultaneously because the metal-organic framework materials constructed centered on trivalent metal indium ion are with higher
Thermodynamic stability is laid a good foundation to be widely applied for it.
Hydrazine is a kind of colourless oil liquid with strong reducing property and toxicity, has in industrial circle and is widely applied very much.
However to the pollution of environment and there is carcinogenicity to human body due to it, hydrazine is considered all extremely harmful to environment and human body
Substance, therefore be the research being of great significance to the detection of hydrazine.Traditional hydrazine detection method has titration, ratio
Color method, chromatography etc., however these methods have certain defect, such as time-consuming or sensitivity are low.
Summary of the invention
The object of the present invention is to provide 2,5- dihydric para-phthalic acid's indiums that a kind of pair of hydrazine hydrate has fluorescence response
The preparation method of complex and the complex.
For above-mentioned purpose, the structural unit of 2,5-Dihydroxyterephthalic acid indium complex of the present invention is
In2(DOBDC)2(OH)2, indium ion is positive trivalent in formula, and DOBDC represents 2, the 5- dihydroxy for losing hydrogen atom on two carboxyls
Terephthalic acid (TPA) dianion, hydroxyl are negative monovalence；It belongs to cubic system, Cmca space group, and cell parameter a isB isC isα is 90 °, and β is 90 °, and γ is 90 °.
Above-mentioned 2,5- dihydric para-phthalic acid indium base complex the preparation method comprises the following steps: by 2,5- dihydric para-phthalic acid
With inidum chloride be the addition N,N-dimethylformamide of 1:1.5~2.5 in molar ratio and water, isopropanol volume ratio are 1:1:4~5
In the mixed solvent, ultrasonic disperse is uniform, sealing, stands reaction 2~4 days, cooled to room temperature, preparation in 80~85 DEG C of constant temperature
At 2,5- dihydric para-phthalic acid's indium complex.
2,5- dihydric para-phthalic acid indium base complex of the present invention can be used as fluorescent optical sensor and be hydrated for fluorescence detection
Hydrazine.
The present invention is prepared into 2,5- dihydroxy to benzene two using 2,5-Dihydroxyterephthalic acid as ligand, using solvent-thermal method
Formic acid indium complex, wavelength corresponding to the maximum emission peak of the complex is at 450 ± 2nm.The complex is to hydration simultaneously
Hydrazine has high susceptibility, in the case where excitation wavelength is 275nm, slit width is 1.8nm, with addition hydrazine hydrate concentration
Increase, fluorescent emission intensity gradually decreases, and when the hydrazine hydrate of addition reaches certain value, it is sudden fluorescence will to occur for compound
It goes out；And it is not high to the sensibility of ammonium hydroxide and hydroxylamine solution, illustrate that the complex can be used as three kinds of hydride of difference nitrogen
Fluorescent optical sensor detects hydrazine hydrate, while excluding the interference of ammonium hydroxide and azanol, and detection sensitivity is high, to hydrazine hydrate
Minimum detection limit can achieve 1ppm.
Detailed description of the invention
Fig. 1 is the crystal structure figure of 2,5- dihydric para-phthalic acid's indium complex prepared by embodiment 1.
Fig. 2 is the tomograph of 2,5- dihydric para-phthalic acid's indium complex prepared by embodiment 1.
Fig. 3 is fluorescent liquid light of the 2,5- dihydric para-phthalic acid indium complex to hydrazine hydrate of the preparation of embodiment 1
Spectrogram.
Fig. 4 is fluorescent liquid spectrogram of the 2,5- dihydric para-phthalic acid indium complex to ammonium hydroxide of the preparation of embodiment 1.
Fig. 5 is fluorescent liquid spectrogram of the 2,5- dihydric para-phthalic acid indium complex to azanol of the preparation of embodiment 1.
Fig. 6 is the face that 2,5- dihydric para-phthalic acid indium complex prepared by embodiment 1 changes with hydrazine hydrate concentration
Color change figure.
Specific embodiment
The present invention is described in more detail with reference to the accompanying drawings and examples, but the present invention is not limited to these Examples.
Embodiment 1
By 0.022g (0.1mmol) inidum chloride, 0.010g (0.05mmol) 2,5- dihydric para-phthalic acid, 4mL isopropyl
Alcohol, 1mL distilled water and 1mL n,N-Dimethylformamide are added in 20mL vial, room temperature ultrasound 30 minutes, sealing, and 85 DEG C
Constant temperature stands reaction 3 days, cooled to room temperature, and filtering is washed 3 times with pentane, drying is purged in nitrogen atmosphere, prepares
It is In at structural unit2(DOBDC)2(OH)22,5-Dihydroxyterephthalic acid indium complex, indium ion is positive trivalent in formula,
DOBDC, which is represented, loses the 2,5-Dihydroxyterephthalic acid dianion of hydrogen atom on two carboxyls, and hydroxyl is negative monovalence,
Yield is 60.5%.
The mono-crystalline structures of prepared 2,5-Dihydroxyterephthalic acid indium complex as shown in Figure 1, belong to cubic system,
Cmca space group, cell parameter a areB isC isα is 90 °, and β is 90 °, and γ is 90 °,
There are 1 In in its separate unit3+, 2 hydroxyl groups, 1 2,5-Dihydroxyterephthalic acid ligand, 2,5- dihydroxy are to benzene
Dioctyl phthalate loses the hydrogen atom on two carboxyls, two unit negative charges of band, and In (III) atom in center is hexa-coordinate mode, respectively
It is carried out with oxygen atom O7, O7a from hydrone and O2, O2a, O2b, O2c atom from 2,5- dihydric para-phthalic acid
(bond distance is respectively as follows: for coordination Bond angle is respectively as follows: O (7a)-In (1)-O
(7)=173.83 (2) °, O (7a)-In (1)-O (1b)=91.23 (12) °, O (7)-In (1)-O (1b)=93.20 (11) °, O
(7a)-In (1)-O (1)=93.20 (11) °, O (7)-In (1)-O (1)=91.23 (12) °, O (1b)-In (1)-O (1)=
88.2 (2) °, O (7a)-In (1)-O (2c)=89.60 (12) °, O7-In (1)-O (2c)=85.81 (11) °, O (1b)-In
(1)-O (2c)=177.75 (13) °, O (1)-In (1)-O (2c)=93.85 (17) °, O (7a)-In (1)-O (2d)=85.81
(11) °, O (7)-In (1)-O (2d)=89.60 (12) °, O (1b)-In (1)-O (2d)=93.85 (17) °, O (1)-In (1)-O
(2d)=177.75 (13) °, O (2c)-In (1)-O (2d)=84.1 (2) °).
The tomograph of prepared 2,5-Dihydroxyterephthalic acid indium complex is as shown in Fig. 2, indium ion is being tied
One-dimensional indium chain is formed in structure, three-dimensional porous material is connected by 2,5-Dihydroxyterephthalic acid, hydroxyl is distributed in duct.
Embodiment 2
Application of the 2,5- dihydric para-phthalic acid indium complex of embodiment 1 in fluorescence detection hydrazine hydrate
2,5-Dihydroxyterephthalic acid indium complex is added in n,N-Dimethylformamide, quality-volume is configured to
Concentration is the complex solution of 1mg/mL；Then the hydrazine hydrate, ammonium hydroxide, hydroxyl of various concentration are separately added into complex solution
Amine carries out 2,5-Dihydroxyterephthalic acid indium complex to hydrazine hydrate, ammonium hydroxide and azanol using PELS55 Fluorescence Spectrometer
Fluorescent detection capabilities research, as a result see Fig. 3~5.
As seen from Figure 3, wavelength corresponding to the maximum emission peak of the complex is at 450 ± 2nm.It is in excitation wavelength
275nm, slit width are under 1.8nm, with the increase that hydrazine hydrate solution concentration is added, the fluorescent emission intensity of the complex
It gradually decreases.When the concentration of the hydrazine hydrate solution of addition reaches 5500ppm, fluorescent quenching occurs for complex.It is computed, it should
Complex is under above-mentioned concentration to the quenching rate K of hydrazine hydrateSV(KSV=(I0-I)/I0(I0Body is detected when for hydrazine hydrate is not added
The fluorescence intensity of system, I are the fluorescence intensity that system is corresponded to when various concentration hydrazine hydrate is added)) up to 80.15%, Cong Tuzhong
As can be seen that the complex can achieve 1ppm to the minimum detection limit of hydrazine hydrate.From fig. 4, it can be seen that in control and detection water
It closes under the identical test condition of hydrazine, with the increase that ammonia spirit concentration is added, the fluorescent emission intensity of the complex is basic
It is constant, illustrate the complex to ammonium hydroxide without response.As seen from Figure 5, in the case where controlling test condition identical with detection hydrazine hydrate,
With the increase that hydroxylamine solution concentration is added, the fluorescent emission intensity of the complex is also held essentially constant, and illustrates the complex
To azanol also without response.It is above-mentioned the experimental results showed that, complex of the present invention can be used as difference nitrogen three kinds of hydride fluorescence
Sensor detects hydrazine hydrate, while excluding the interference of ammonium hydroxide and azanol.Fig. 6 is shown with hydrazine hydrate solution concentration
Increase, the color change of the n,N-Dimethylformamide solution of the complex shows the cooperation from macroscopic color change
Object has more convenient practical application in the detection to hydrazine hydrate.
Claims (3)
1. a kind of 2,5-Dihydroxyterephthalic acid indium complex for fluorescence detection hydrazine hydrate, it is characterised in that: this is matched
The structural unit for closing object is In2(DOBDC)2(OH)2, indium ion is positive trivalent in formula, and DOBDC representative loses hydrogen on two carboxyls
The 2,5-Dihydroxyterephthalic acid dianion of atom, hydroxyl are negative monovalence；It belongs to cubic system, Cmca space group,
Cell parameter a isB isC isα is 90 °, and β is 90 °, and γ is 90 °.
2. a kind of preparation method of the 2,5-Dihydroxyterephthalic acid indium base complex of claim 1, it is characterised in that: by 2,
5- dihydric para-phthalic acid and inidum chloride are that N,N-dimethylformamide and water, isopropanol is added in 1:1.5~2.5 in molar ratio
Volume ratio is the in the mixed solvent of 1:1:4~5, and ultrasonic disperse is uniform, sealing, stands reaction 2~4 days in 80~85 DEG C of constant temperature,
Cooled to room temperature is prepared into 2,5-Dihydroxyterephthalic acid indium complex.
3. purposes of the 2,5- dihydric para-phthalic acid's indium base complex of claim 1 in fluorescence detection hydrazine hydrate.
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| CN110256472A (en) * | 2019-06-18 | 2019-09-20 | 陕西师范大学 | Indium-aromatic carboxylic acids porous coordination and preparation method thereof and the application in lithium ion battery |
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|---|---|---|---|---|
| CN103740361A (en) * | 2013-12-24 | 2014-04-23 | 浙江大学 | Dye/metal-organic framework composite material for white light emission and preparation method thereof |
| JP2018095945A (en) * | 2016-12-16 | 2018-06-21 | 富士通株式会社 | Adsorbent and production method of the same, electrode for carbon dioxide and reduction and carbon dioxide reduction device |
| CN108570062A (en) * | 2018-05-31 | 2018-09-25 | 陕西师范大学 | A kind of porous metals organic coordination compound and preparation method thereof and the application in detection ammonia, ammonium hydroxide |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740361A (en) * | 2013-12-24 | 2014-04-23 | 浙江大学 | Dye/metal-organic framework composite material for white light emission and preparation method thereof |
| JP2018095945A (en) * | 2016-12-16 | 2018-06-21 | 富士通株式会社 | Adsorbent and production method of the same, electrode for carbon dioxide and reduction and carbon dioxide reduction device |
| CN108570062A (en) * | 2018-05-31 | 2018-09-25 | 陕西师范大学 | A kind of porous metals organic coordination compound and preparation method thereof and the application in detection ammonia, ammonium hydroxide |
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| CN110256472A (en) * | 2019-06-18 | 2019-09-20 | 陕西师范大学 | Indium-aromatic carboxylic acids porous coordination and preparation method thereof and the application in lithium ion battery |
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