CN105524095A - One-dimensional morpholine cadmium complex single crystal and preparation method and application thereof - Google Patents
One-dimensional morpholine cadmium complex single crystal and preparation method and application thereof Download PDFInfo
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- CN105524095A CN105524095A CN201610001172.XA CN201610001172A CN105524095A CN 105524095 A CN105524095 A CN 105524095A CN 201610001172 A CN201610001172 A CN 201610001172A CN 105524095 A CN105524095 A CN 105524095A
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- 239000013078 crystal Substances 0.000 title claims abstract description 25
- -1 morpholine cadmium Chemical compound 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 20
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000975 dye Substances 0.000 claims description 20
- 230000000274 adsorptive effect Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000005260 alpha ray Effects 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 238000001514 detection method Methods 0.000 abstract description 2
- QOYRNHQSZSCVOW-UHFFFAOYSA-N cadmium nitrate tetrahydrate Chemical compound O.O.O.O.[Cd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QOYRNHQSZSCVOW-UHFFFAOYSA-N 0.000 abstract 2
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910010413 TiO 2 Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002780 morpholines Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
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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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/48—Systems using polarography, i.e. measuring changes in current under a slowly-varying voltage
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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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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Abstract
The present invention discloses a one-dimensional morpholine cadmium complex single crystal and a preparation method and application thereof, the structure is shown as [Cd (ipa) (H2O) (mpl)] 2mpl, wherein mpl = morpholine, and ipa = isophthalic acid. The present invention also discloses the preparation method of the single crystal. A normal temperature volatilization method is used, to be more specific, mpl, Cd (NO3) 2.4H2O and ipa are stirred in water for half an hour and then filtered, and the filtrate is volatilized at normal temperature for two weeks to obtain a colorless bulk crystal suitable for X-ray single crystal diffraction, wherein molar ratio of mpl to Cd (NO3) 2.4H2O to ipa is 1: 1: 1. The present invention further discloses application of the one-dimensional morpholine cadmium complex single crystal as a potential fluorescent material in detection of adsorption quantity of a dye or an emitting agent.
Description
The present invention obtains the subsidy that state natural sciences fund general project (21471113), Tianjin Education Commission general project (20140506) and Tianjin Normal University's Middl-age and youth faculty Academic innovations advance planning item (52XC1401).
Technical field
The invention belongs to organic and Inorganic synthese technical field, relate to one dimension morpholine cadmium complex monocrystalline [Cd (ipa) (H
2o) (mpl)] preparation method of 2mpl and the application as potential fluorescent material, wherein, mpl=morpholine; Ipa=m-phthalic acid.
Background technology
Morpholine class title complex is due to the diversity of its structure, and the advantages such as Modulatory character, outstanding thermostability, all have potential application prospect in multiple fields such as separation, chirality and catalysis, nonlinear optics, molecular recognition.Therefore, as functional molecular material of new generation, the research and development of the synthesis of morpholine class title complex and design, structure and functional performance have become one of Disciplinary Frontiers of functional molecular material scientific development.
The present invention adopts normal temperature volatilization method, i.e. mpl, ipa and Cd (NO
3)
24H
2o filters stir half an hour in water after, and filtrate normal temperature obtains applicable X-ray single crystal diffraction colourless bulk crystal structure after volatilizing two weeks is [Cd (ipa) (H
2o) (mpl)] 2mpl, wherein, mpl=morpholine; Ipa=m-phthalic acid.This title complex also can be used as potential fluorescent material aspect and is applied.
Summary of the invention
Current inventor provides following technical scheme for this reason:
A kind of monocrystalline of one dimension morpholine cadmium complex, it is characterized in that this single crystal structure adopts APEXIICCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray, λ=0.71073 is incident radiation, point diffraction is collected with ω-2 θ scan mode, obtain unit cell parameters through least-squares refinement, utilize software to solve single crystal data from difference Fourier electron density map:
Its structure is as follows:
[Cd (ipa) (H
2o) (mpl)] 2mpl, wherein
Mpl=morpholine;
Ipa=m-phthalic acid.
The present invention further discloses the preparation method of one dimension morpholine cadmium complex monocrystalline, it is characterized in that it adopts normal temperature volatilization method, by mpl, ipa and Cd (NO
3)
24H
2o filters stir half an hour in water after, and filtrate normal temperature obtains the colourless bulk crystals of applicable X-ray single crystal diffraction after volatilizing two weeks; Wherein mpl:ipa:Cd (NO
3)
2the mol ratio of 4H2O is 1:1:1;
The structure of one dimension morpholine cadmium complex monocrystalline is [Cd (ipa) (H
2o) (mpl)] 2mpl; Wherein, mpl=morpholine; Ipa=m-phthalic acid;
mplipa。
The present invention further discloses one dimension morpholine cadmium complex monocrystalline as the application of potential fluorescent material in the adsorptive capacity detecting dyestuff or luminous agent, and experimental result shows:
(1) complex monocrystal in embodiment 1 has good selectivity and susceptibility to dyestuff, and detectability reaches 0.1ppm.
(2) can detect the luminous agent of trace, detection limit reaches 5.0 μ g/L.
(3) complex monocrystal that prepared by embodiment 1 is 1.4 × 10 for the adsorptive capacity of dyestuff
-3mol/cm
2.
The present invention's preferred example:
Morpholine (mpl) (0.1mmol), m-phthalic acid (ipa) (0.1mmol) and Cd (NO
3)
24H
2o (0.1mmol) filters stir half an hour in water (10mL) after, and filtrate normal temperature obtains the colourless bulk crystals of applicable X-ray single crystal diffraction after volatilizing two weeks.Productive rate: 40%.Ultimate analysis (C
20h
32cdN
3o
8) theoretical value (%): C, 43.29; H, 5.81; N, 7.57.Measured value: C, 43.33; H, 5.89; N, 7.52.
The advantage and disadvantage that a kind of one dimension morpholine cadmium complex monocrystalline disclosed by the invention has is:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) the one dimension morpholine cadmium complex monocrystalline prepared by the present invention, production cost is low, and method is easy, is applicable to scale operation.The photoelectric response range problem widening dyestuff can be solved at dyestuff or luminous agent application aspect.
Accompanying drawing explanation
Fig. 1: the crystalline structure figure of complex monocrystal;
Fig. 2: the one-dimensional catenary structure figure of complex monocrystal.
Embodiment
Below in conjunction with embodiment, the present invention is described further, and embodiment is only indicative, never means that it limits the scope of the invention by any way.Raw materials used all have commercially available.All raw materials are all buy from chemical reagents corporation both domestic and external, such as morpholine, m-phthalic acid and Cd (NO
3)
24H
2the raw materials such as O, through continuation purify but directly use.
Embodiment 1
Morpholine (mpl) (0.1mmol), m-phthalic acid (ipa) (0.1mmol) and Cd (NO
3)
24H
2o (0.1mmol) filters stir half an hour in water (10mL) after, and filtrate normal temperature obtains the colourless bulk crystals of applicable X-ray single crystal diffraction after volatilizing two weeks.Productive rate: 40%.Ultimate analysis (C
20h
32cdN
3o
8) theoretical value (%): C, 43.29; H, 5.81; N, 7.57.Measured value: C, 43.33; H, 5.89; N, 7.52.
Embodiment 2
Crystal structure determination adopts APEXIICCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray, λ=0.71073 is incident radiation, point diffraction is collected with ω-2 θ scan mode, unit cell parameters is obtained through least-squares refinement, software is utilized to solve crystalline structure from difference Fourier electron density map, and through Lorentz lorentz and polarizing effect correction.All H atom are synthesized by difference Fourier and are determined through desirable position calculation.Detailed axonometry data:
Embodiment 3
The concrete instance that dyestuff or luminous agent use
Method: the PARSTAT2273 electrochemical workstation of differentiated pulse volt-ampere (DPV) the curve negotiating Princeton Applied Research Laboratory development of dye solution is measured.The DPV test of solution adopts three-electrode system, and glass-carbon electrode is working electrode, and supporting electrode is platinum plate electrode, homemade Ag/AgNO
3electrode is reference electrode; Electrolytic solution is the acetonitrile solution of 0.1molL-1TBAP.Reduce reversible point to for interior mark with Oxidation of Ferrocene, obtains the correction value between test system and standard hydrogen electrode system.
Monochromatic incident light photoelectric transformation efficiency (IPCE) describes the photoelectric transformation efficiency of DSCs under monochromatic ray effect, is transfer to the electronic number of external circuit and the ratio of incident light subnumber.During measurement, use 500W xenon lamp as light source, the monochromatic ray of incident light under the multifunctional assembled grating spectrograph of WDS-5 type obtains different wave length λ; Monochromatic light exposure, in the light anode of battery, reads current value I by Keithley2400 digital sourcemeter.Monochromatic good fortune illumination is measured by USB4000plug-and-play Miniature optical linear light spectrometer.
Step: in order to definitely understand dyestuff at TiO
2adsorptive capacity on film, complex monocrystal dye sensitization TiO prepared by embodiment 1
2(geometric area is about 1cm to nanometer crystal film
2) be immersed in 10mL0.01molL
-1sodium hydroxide methanol solution in spend the night, treat that the absorbancy of attached mensuration solution separated completely by dyestuff.Wash one's face and rinse one's mouth according to absorbancy and molar absorptivity and can calculate the adsorptive capacity of dyestuff on unit surface nanometer crystal film.The adsorptive capacity of this complex monocrystal is 1.4 × 10
-3mol/cm
2.
Result: compared with the methanol solution of dyestuff, complex monocrystal dyestuff is at TiO
2absorption spectrum on film all obviously broadens and red shift.This shows that dye molecule is at TiO
2define the J-aggregate of first also tail.From the principle of work of DSCs, the spectrum broadening that dye aggregation causes and red shift are very favourable for the widening of photoelectric response scope of dyestuff.But meanwhile, dye aggregation cognition reduces its electron injection efficiency greatly, thus causes the degraded performance of DSCs.So, in dye solution, usually add coadsorbent to suppress the gathering of dyestuff.This complex monocrystal is in methanol solution and at TiO
2the fluorometric investigation of the purple solution on membrane electrode adopts 2.5 × 10
-5the methanol solution of mol/L, maximum emission wavelength is positioned at 500nm.
Embodiment 4
One dimension morpholine cadmium complex monocrystalline is as the application preparing luminescent material.
Method: by spectrophotofluorometer, carries out the excitation wavelength of this compound monocrystal (embodiment 1) and the scanning of emission wavelength respectively, selects and determine optimal wavelength.
Conclusion: excitation wavelength and the emission wavelength of this compound are respectively 340nm and 500nm.
Step: one dimension morpholine cadmium complex monocrystalline grinding compressing tablet is become the sheet sample that external diameter is 27mm, thickness is about 3mm, and the sample pool putting into MPF-4 fluorescence spectrophotometer is measured.
Result: the excitation wavelength lambda of this compound
ex=340nm, emission wavelength lambda
em=500nm.
After the preferred embodiment described in detail, be familiar with this technology personage can be well understood to, do not departing under above-mentioned claim and spirit and can carry out various change and amendment, all above embodiment is done according to technical spirit of the present invention any simple modification, equivalent variations and modification, all belong to the scope of technical solution of the present invention.And the present invention is not also by the restriction of example embodiment in specification sheets.
Claims (3)
1. the monocrystalline of an one dimension morpholine cadmium complex, it is characterized in that this single crystal structure adopts APEXIICCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray, λ=0.71073 is incident radiation, point diffraction is collected with ω-2 θ scan mode, obtain unit cell parameters through least-squares refinement, utilize software to solve single crystal data from difference Fourier electron density map:
Its structure is as follows:
[Cd (ipa) (H
2o) (mpl)] 2mpl, wherein
Mpl=morpholine;
Ipa=m-phthalic acid.
2. the preparation method of one dimension morpholine cadmium complex monocrystalline described in claim 1, is characterized in that it adopts normal temperature volatilization method, by mpl, ipa, Cd (NO
3)
24H
2o filters stir half an hour in water after, and filtrate normal temperature obtains the colourless bulk crystals of applicable X-ray single crystal diffraction after volatilizing two weeks;
Wherein mpl:ipa:Cd (NO
3)
24H
2the mol ratio of O is 1:1:1;
The structure of one dimension morpholine cadmium complex monocrystalline is [Cd (ipa) (H
2o) (mpl)] 2mpl; Wherein mpl=morpholine; Ipa=m-phthalic acid;
mplipa。
3. one dimension morpholine cadmium complex monocrystalline described in claim 1 is as the application of potential fluorescent material in the adsorptive capacity detecting dyestuff or luminous agent.
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Cited By (1)
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CN109400893A (en) * | 2018-09-21 | 2019-03-01 | 皖西学院 | The preparation and its application of the two-dimentional micropore cadmium compound in active site |
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CN104592262A (en) * | 2015-02-26 | 2015-05-06 | 天津师范大学 | Zinc anthracene cyclo-bis(triazolyl) isophthalate complex used as potential fluorescent material and preparation method of zinc anthracene cyclo-bis(triazolyl) isophthalate complex |
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CN104592271A (en) * | 2015-02-26 | 2015-05-06 | 天津师范大学 | Cadmium isophthalate anthracene cyclo-bis(triazolyl) complex used as potential fluorescent material and preparation method of cadmium isophthalate anthracene cyclo-bis(triazolyl) complex |
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Non-Patent Citations (1)
Title |
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H S MOON. ET AL: ""Preparation and one-dimensional coordination structure of the bis(morpholine)dithiocyanatocadmium(II) complex, [Cd(SCN)2(C4H9NO)2]"", 《BULL KOREAN CHEM SOC》 * |
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CN109400893A (en) * | 2018-09-21 | 2019-03-01 | 皖西学院 | The preparation and its application of the two-dimentional micropore cadmium compound in active site |
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