CN106929007B - A kind of cyanic colours fluorescent material and preparation method thereof - Google Patents
A kind of cyanic colours fluorescent material and preparation method thereof Download PDFInfo
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- CN106929007B CN106929007B CN201710142879.7A CN201710142879A CN106929007B CN 106929007 B CN106929007 B CN 106929007B CN 201710142879 A CN201710142879 A CN 201710142879A CN 106929007 B CN106929007 B CN 106929007B
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- 239000000463 material Substances 0.000 title claims abstract description 39
- 239000003086 colorant Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229910052793 cadmium Inorganic materials 0.000 claims abstract description 17
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 11
- 229910001220 stainless steel Inorganic materials 0.000 claims abstract description 8
- 239000010935 stainless steel Substances 0.000 claims abstract description 8
- IFOZXUMSHBVSMA-UHFFFAOYSA-N 5-nitro-2,4-dioxo-1h-pyrimidine-6-carboxylic acid;potassium Chemical compound [K].OC(=O)C=1NC(=O)NC(=O)C=1[N+]([O-])=O IFOZXUMSHBVSMA-UHFFFAOYSA-N 0.000 claims abstract description 7
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012153 distilled water Substances 0.000 claims abstract description 6
- AGHQMAQBLOTWPQ-UHFFFAOYSA-H cadmium sulfate hydrate Chemical compound O.O.O.O.O.O.O.O.[Cd+2].[Cd+2].[Cd+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O AGHQMAQBLOTWPQ-UHFFFAOYSA-H 0.000 claims abstract description 5
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000013078 crystal Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- WJFDCFHWFHCLIW-UHFFFAOYSA-N 2-(bromomethyl)-6-methylpyridine Chemical compound CC1=CC=CC(CBr)=N1 WJFDCFHWFHCLIW-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 3
- -1 Carboxyl Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- QCUOBSQYDGUHHT-UHFFFAOYSA-L cadmium sulfate Chemical group [Cd+2].[O-]S([O-])(=O)=O QCUOBSQYDGUHHT-UHFFFAOYSA-L 0.000 claims 1
- 229910000369 cadmium(II) sulfate Inorganic materials 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000001027 hydrothermal synthesis Methods 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 238000011953 bioanalysis Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000009994 optical bleaching Methods 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C07F3/08—Cadmium 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
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The invention discloses a kind of cyanic colours fluorescent material and preparation method thereof, which is the cadmium complex with certain space structure, skeleton symbol: [Cd (C4N3O5)(C12H8N2)(H2O)]n;Its chemical formula are as follows: CdC16H10N5O6, crystallographic system is monocline, space group C2/m, brilliant bag parameter α=90 °, β=107.10 °, γ=90 °, cadmium ion use the coordination mode of seven coordination configurations.The preparation method of the fluorescent material compound is to be placed in stainless steel cauldron, obtained cadmium complex by hydro-thermal reaction the mixtures such as Cadmium sulfate hydrate, 1,10- phenanthroline and 5- nitroorotic acid potassium and distilled water.The preparation method is easy to operate, low in cost, is suitble to large-scale production.Cadmium complex produced by the present invention has good cyanic colours fluorescent emission performance, has potential application prospect as fluorescent material.
Description
Technical field
The invention belongs to the technical fields of luminescent material, specifically about a kind of cyanic colours fluorescent material and its preparation side
Method.
Background technique
Since earlier 1900s, the research and application of fluorescent material are developed rapidly, especially organic fluorescence material
Material is widely used in weaving coloring, coloring plastic and printing color.Fluorescent material refer to material in the case where external light source is irradiated,
To obtain energy, generating excitation leads to luminous phenomenon.Ultraviolet radioactive, visible light and infra-red radiation can cause fluorescent material
It shines.There are many purposes for fluorescent material, and street road sign, building doorplate label, fire protection safety sign, billboard can be made with it
Deng.Fluorescent material is widely used in dyestuff, photooxidant, Optical Bleaching Agent, the numerous areas such as chemistry and bioanalysis, it
All have broad application prospects in terms of materia medica, physiology, environmental science, information science technology.
Organic fluorescence materials usually have the group or structure that can absorb exciting light, usually conjugation bond structure, such as: conjugation
Pi bond, benzene ring structure or similar benzene ring structure.Some organic ligands itself are luminous weaker, become strong hair after forming metal complex
Stimulative substance, such as 8-hydroxyquinoline itself hardly shine, but the 8-hydroxyquinoline aluminum complex formed has hair well
Optical property is the star molecule in luminescent substance.Certain presence of Schiff-base complex also have good luminescent properties (Hamada Y etc.
J.Appl.Phys.,1996,35,L1339).Increasingly deep, the new metal organic complexes that fluorescent material is studied with people
Object is continued to bring out as fluorescent material.Nitroorotic acid complex has few quantifier elimination to report as fluorescent material, such as Hu Xiufeng
Et al. report a kind of purple fluorescence material and preparation method thereof, grant number CN102329610B;Li Xing, Bing Yue et al. are reported
The cadmium of purple luminescence property-nitroorotic acid compound (CrystEngComm, 2011,13,6373).The present invention discloses a kind of tool
There is the cadmium complex of specific composition and space structure, excites the complex under light action to have stronger fluorescent emission in 330nm, most
Big emission peak 470nm has potential application prospect as fluorescent material.
Summary of the invention
The technical problem to be solved by the present invention is to be directed to the prior art, provide a kind of emanative glimmering with good cyanic colours
Luminescent material and preparation method thereof.
The technical solution that the present invention is taken regarding to the issue above are as follows: a kind of cyanic colours fluorescent material, the cyanic colours fluorescence
Material is the cadmium complex with certain space structure, skeleton symbol: [Cd (C4N3O5)(C12H8N2)(H2O)]n, chemical formula
Are as follows: CdC16H10N5O6, crystallographic system is monocline, space group C2/m, brilliant bag parameter
α=90 °, β=107.10 °, γ=90 °, cadmium ion use the coordination mode of seven coordination configurations.
The preparation method of above-mentioned cyanic colours fluorescent material, comprising the following steps:
(1) a certain amount of Cadmium sulfate hydrate (CdSO is weighed4·H2O), a certain amount of 5- nitroorotic acid potassium and 1,10- are luxuriant and rich with fragrance
Sieve quinoline is placed in the polytetrafluoroethyllining lining of 25mL stainless steel cauldron, adds the distilled water of 10~15mL, stirs 20~30min,
Obtain reaction mixture solution, Cd (II): 5- nitroorotic acid root in reaction mixture solution: ratio=1 of the amount of substance of phenanthroline
~1.5:1:1;
(2) sealing is placed in air dry oven equipped with the stainless steel cauldron of above-mentioned reaction mixture solution, 120~
160 DEG C are reacted 48~72 hours, and reaction terminates to be cooled to room temperature, are opened reaction kettle and are obtained colourless acicular crystal;
(3) colourless acicular crystal is taken out, is washed with dehydrated alcohol, it is dry, that is, obtain the cyanic colours fluorescent material.
Preferably, the substance for participating in reaction is that chemistry is pure.
Compared with prior art, present invention is characterized in that
With Cadmium sulfate hydrate, 5- nitroorotic acid potassium and 1,10- phenanthroline is that raw material carries out hydro-thermal reaction in autoclave,
The carboxyl of 5- nitroorotic acid is sloughed during the reaction and in-situ oxidation is at carbonyl (- C=O), the N of carbonyl and ligand ortho position
One Cd (II) ion of chelating forms quaternary chelating ring, is expanded into one-dimensional chain structure (Fig. 1) by chelating, which has rigid
Property conjugate property, be conducive to electron transition and energy transmission, thus make compound have good optical activity.The hydro-thermal reaction
A kind of novel cadmium complex is synthesized, which has accurate space structure and accurate molecular formula, as a kind of ultramarine
Color luminescent material has a good application prospect.
Detailed description of the invention
Fig. 1 is the coordination context diagram of metal ion in cyanic colours fluorescent material cadmium complex of the invention;
Fig. 2 is the fluorescence emission spectrum of cyanic colours fluorescent material cadmium complex of the invention.
Specific embodiment
The present invention is further told about in detail below in conjunction with figure embodiment.
Embodiment 1:
Weigh the CdSO of 0.0226g (0.1mmol)4·H2The 5- nitroorotic acid potassium list water of O, 0.0257g (0.1mmol)
Object is closed, hydration 1, a 10- phenanthroline of 0.0198 (0.1mmol) is placed in the polytetrafluoroethyllining lining of 25mL stainless steel cauldron
In, add the distilled water of 10mL, stirs 20min, obtain reaction mixture solution;Sealing is stainless equipped with above-mentioned reaction mixture solution
Steel reaction kettle is placed in air dry oven, and 120 DEG C are reacted 48 hours, and reaction terminates to be cooled to room temperature, is opened reaction kettle and is obtained nothing
Color acicular crystal;Colourless acicular crystal is taken out, is washed with dehydrated alcohol, dry, i.e. acquisition cyanic colours fluorescent material cadmium cooperation
Object.
Embodiment 2:
Weigh the CdSO of 0.0339g (0.15mmol)4·H2The 5- nitroorotic acid potassium list water of O, 0.0257g (0.1mmol)
Object is closed, hydration 1, a 10- phenanthroline of 0.0198 (0.1mmol) is placed in the polytetrafluoroethyllining lining of 25mL stainless steel cauldron
In, add the distilled water of 15mL, stirs 30min, obtain reaction mixture solution;Sealing is stainless equipped with above-mentioned reaction mixture solution
Steel reaction kettle is placed in air dry oven, and 160 DEG C are reacted 72 hours, and reaction terminates to be cooled to room temperature, is opened reaction kettle and is obtained nothing
Color acicular crystal;Colourless acicular crystal is taken out, is washed with dehydrated alcohol, dry, i.e. acquisition cyanic colours fluorescent material cadmium cooperation
Object.
Embodiment 3:
Weigh the CdSO of 0.0339g (0.15mmol)4·H2The 5- nitroorotic acid potassium list of O, 0.0308g (0.12mmol)
Hydrate, hydration 1, a 10- phenanthroline of 0.0238 (0.12mmol), is placed in the polytetrafluoroethylene (PTFE) of 25mL stainless steel cauldron
In lining, add the distilled water of 15mL, stirs 25min, obtain reaction mixture solution;Sealing is equipped with above-mentioned reaction mixture solution not
Rust steel reaction kettle is placed in air dry oven, and 150 DEG C are reacted 60 hours, and reaction terminates to be cooled to room temperature, is opened reaction kettle and is obtained
Colourless acicular crystal;Colourless acicular crystal is taken out, is washed with dehydrated alcohol, dry, i.e. acquisition cyanic colours fluorescent material cadmium is matched
Close object.
Obtained cyanic colours fluorescent material cadmium complex is colourless acicular crystal, chemical formula in above-described embodiment are as follows:
CdC16H10N5O6, skeleton symbol are as follows: [Cd (C4N3O5)(C12H8N2)(H2O)]n;The 5- nitroorotic acid decarboxylation in hydro-thermal reaction
Oxidation and chelating schematic diagram are as follows:
The coordination context diagram of metal ion is as shown in Figure 1 (for illustrative clarity, hydrogen in cyanic colours fluorescent material cadmium complex
Atom is omitted, and the atom that symmetry operation comes out does not mark).
Fluorescence property test is carried out after obtained cyanic colours fluorescent material cadmium complex is air-dried, in 330nm exciting light
Acting on the lower cadmium complex has stronger fluorescent emission, maximum emission peak 470nm, it is shown that good cyanic colours fluorescent emission
Can, fluorescence spectrum is as shown in Figure 2.
Claims (2)
1. a kind of cyanic colours fluorescent material, which is characterized in that the fluorescent material is the cadmium complex with certain space structure,
Skeleton symbol: [Cd (C4N3O5)(C12H8N2)(H2O)]n;Its chemical formula are as follows: CdC16H10N5O6, crystallographic system is monocline, and space group is
C2/m, cell parameterα=90 °, β=107.10 °, γ=90 °, C12H8N2
For the molecular formula of 1,10- phenanthroline ligand, C4N3O5Carboxyl for 5- nitroorotic acid is sloughed and in-situ oxidation after carbonyl at forming
The molecular formula of ligand, cadmium ion use the coordination mode of seven coordination configurations, two of them nitrogen from 1,10- phenanthroline ligand,
Other two nitrogen is from C4N3O5Ligand, an oxygen is from water of coordination molecule, and two oxygen are from C4N3O5The carbonyl of ligand;
C4N3O5The carbonyl of ligand and one Cd (II) ion of N chelating at ligand ortho position, form quaternary chelating ring, are expanded by chelating
The complex of one-dimensional chain structure has cyanic colours fluorescent emission performance;
The carboxyl of 5- nitroorotic acid is sloughed and in-situ oxidation is at carbonyl, carbonyl and the N at ortho position chelating Cd (II) ion such as following formula
Shown, M indicates Cd (II) ion in formula;
2. a kind of preparation method of cyanic colours fluorescent material as described in claim 1, which comprises the following steps:
(1) a certain amount of Cadmium sulfate hydrate, 5- nitroorotic acid potassium and 1 are weighed, 10- phenanthroline is placed in 25mL stainless steel reaction
In the polytetrafluoroethyllining lining of kettle, add the distilled water of 10~15mL, stir 20~30min, obtain reaction mixture solution, reaction is mixed
Cd (II): 5- nitroorotic acid root in polymer solution: ratio=1~1.5:1:1 of the amount of substance of phenanthroline;
(2) sealing is placed in air dry oven equipped with the stainless steel cauldron of above-mentioned reaction mixture solution, and 120~160 DEG C
Reaction 48~72 hours, reaction terminate to be cooled to room temperature, open reaction kettle and obtain colourless acicular crystal;
(3) colourless acicular crystal is taken out, is washed with dehydrated alcohol, it is dry, that is, obtain the cyanic colours fluorescent material;
The chemical formula of the Cadmium sulfate hydrate is CdSO4·H2O;
The substance for participating in reaction is that chemistry is pure.
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