CN103468244A - Quinoline derivative intercalated hydrotalcite-like multicolor luminescent material and preparation method thereof - Google Patents
Quinoline derivative intercalated hydrotalcite-like multicolor luminescent material and preparation method thereof Download PDFInfo
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- CN103468244A CN103468244A CN2013103475953A CN201310347595A CN103468244A CN 103468244 A CN103468244 A CN 103468244A CN 2013103475953 A CN2013103475953 A CN 2013103475953A CN 201310347595 A CN201310347595 A CN 201310347595A CN 103468244 A CN103468244 A CN 103468244A
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- quinoline
- houghite
- oxine
- hydrotalcite
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Abstract
The invention discloses a quinoline derivative intercalated hydrotalcite-like multicolor luminescent material and a preparation method thereof. The method allows a quinoline derivative to be intercalated into a hydrotalcite-like interlayer by means of the exchangeability of hydrotalcite-like interlayer anions, and allows a light conversion material emitting different color fluorescence in a visible region to be obtained by changing the kind of the quinoline derivative, the kind of the hydrotalcite like metal cations and the intercalation amount of the quinoline derivative, and the thermal stability of the luminescent composite material is improved because of the protection effect of the hydrotalcite-like layered structure. Novel light conversion composite materials emitting strong fluorescence of corresponding metal coordination chelates and different from non-fluorescent hydrotalcite like compounds are prepared. The above functionalized hydrotalcite like material obtained through the method has the advantages of simple preparation, easy operation, environmental protection, no pollution, controllable particle size, and very good compatibility with high-molecular materials.
Description
(1) technical field
The present invention relates to a kind of multicolor luminous material of houghite and preparation method of quinoline intercalation.
(2) background technology
Light-converting agent is that a class can be by daylight, to photosynthesis of plant, harmful or useless UV-light, green glow etc. are converted into the chemical substance of the required ruddiness of photosynthesis, blue light.Current light-converting agent commonly used mainly is divided into organic dye class light-converting agent, inorganic salts light-converting agent, rare earth compounding class light-converting agent.Recent study person attempts to synthesize low cost, turns optical efficiency high, with macromolecular material, the compound light-converting agent of organic-inorganic of fine consistency is arranged.
1987, oxine aluminium (AlQ for Tang
3) made organic electroluminescence device as luminescent layer, afterwards people just constantly using oxine with metal synthetic compound except aluminium as luminescent material.And find a lot of transition metal, the second main group metal, rare earth all can coordinate with oxine the fluorescence of launching different wave length, and has very strong luminous intensity.The glow color of oxine beryllium and AlQ
3similar, emission wavelength is also in the 520nm left and right; Oxine magnesium sends strong blue-greenish colour fluorescence, and maximum emission wavelength is about 528nm; Oxine zinc can send gold-tinted in the 568nm left and right; Oxine gallium, zirconium, cobalt, europium, manganese, cadmium etc. all can send strong fluorescence.The photoluminescence of these metallo-chelates is that the part of part acceptor center ion slight interference is luminous, and the central ion difference, and the fluorescence spectrum of formed inner complex has larger difference on emission wavelength.Except oxine, the investigator also finds that multiple quinoline all can form inner complex with metal ion and send strong fluorescence.Although the quinoline metallo-chelate has the excellent performance such as good thermostability, Broad excitation band and high fluorescence efficiency, be used for one of fluorescent material of luminous or display device by first-selection always.But directly as light-converting agent use that often existing easily reunites and cause quenching of fluorescence, be difficult to the big area film forming, the shortcomings such as cost is high, easy decomposition.
Houghite is a kind of layered metal hydroxides, and the adjustable sex change due to its unique laminate structure and laminate composition and interlayer anion, make it all be widely used in catalysis, ion-exchange, absorption, medicine and other fields as inorganic functional material., owing to having laminate structure, there is strong covalent linkage effect in houghite in layer, and there is electrostatic attraction in interlayer, and has the non covalent bond weak interactions such as electrostatic attraction, hydrogen bond between laminate and interlayer anion, therefore has good thermostability.And houghite is when being heated, and its water of constitution and laminate hydroxyl and interlayer anion are with water and CO
2form deviate from, play and reduce combustion gases concentration, intercept O
2the fire retardation of gas.By the adjustable sex change of houghite interlayer anion, by its modification, at interlayer, mix various fluorescent ligands, obtain new light conversion agent.The people such as Duan Xue in 2005 propose the patent application (number of patent application: 200510012245.7 of " having rare earth compounding intercalated houghite of fluorescent characteristic and preparation method thereof "; Publication number: CN1715365A), tie up to hydrotalcite layers and introduce the ammonia carboxylic title complex of the rare earth ion such as Eu by ion-exchange to obtain the epipolic hydrotalcite of tool.The people such as ground force in 2009 have proposed the patent application (number of patent application: 200910217552.7 of " three (HQS roots) close aluminum complex anion intercalated hydrotalcite composite luminescent material and preparation method thereof "; Publication number: CN101768435A), by three (HQS roots) are closed to the aluminum complex intercalation, enter the houghite interlayer, obtain the hybrid material with photoelectric functional.These reports are all directly to insert metallo-chelate at the houghite interlayer, exist and insert inefficient shortcoming.
Summary of the invention:
The technical problem existed as light conversion agent in order to solve above-mentioned direct use quinoline metallo-chelate.The invention provides a kind of quinoline directly is inserted in houghite as part and forms multicolor luminous matrix material and preparation method thereof; quinoline is inserted into to the houghite interlayer; quinoline can with the houghite laminate on the metallic cation coordination form the specific group assembling structure; improved the asymmetry as the metal complexes of luminescence center; while is due to the provide protection of houghite laminate structure; improved the thermostability of this luminescent composite, and with macromolecular material, good consistency has been arranged.By changing kind, the kind of houghite metallic cation and the intercalation amount of quinoline of quinoline, the houghite that can obtain having different packaging assemblies.And the houghite of each particular group assembling structure can correspondence be launched the fluorescence of specific wavelength, and then obtained the multiple light conversion agent with different emission.
A kind of preparation method of the multicolor luminous material of houghite of quinoline intercalation, comprise the steps:
1) by the standby interlayer anion of hydro-thermal legal system, be Cl-or NO
3 2-, laminate divalence, trivalent metal cation mol ratio M
2+/ M
3+=2.0~4.0, M wherein
2+the concentration houghite precursor that is 0.2~1.0mol/L.
2) the houghite precursor prepared by step 1) joins in the aqueous solution of quinoline and is reacted, houghite precursor 0.5g/L, quinoline 10~50g/L in the aqueous solution, stirring velocity is 2000~4000 rev/mins, under 30~60 ℃, react 12~24 hours, standing 10~20 hours, use the ethanol centrifuge washing, 30~60 ℃ of dryings 12~24 hours, obtain the multicolor luminous matrix material of houghite of quinoline intercalation.
Divalent metal M of the present invention
2+for Fe
2+, Co
2+, Cu
2+, Zn
2+, Mn
2+, Ca
2+, Mg
2+or Ni
2+; Trivalent metal cation M
3+for Al
3+, Cr
3+, Mn
3+, Fe
3+, Ce
3+, Eu
3+or Sm
3+.
Quinoline of the present invention is oxine, 2,6-dihydroxyl quinoline, 4,8-dihydroxyl quinaldic acid, HQS, 5-nitro-oxine, 4-methyl-oxine or 2,4-dihydroxyl quinoline.
The multicolor luminous matrix material of houghite of the quinoline intercalation that utilizes the present invention to prepare can be by changing kind, the kind of houghite metallic cation and the intercalation amount of quinoline of quinoline, obtain the multiple light conversion agent of launching different colours fluorescence, and equipment is simple, easy to operate, Product Green is environment friendly and pollution-free, particle diameter is controlled, with macromolecular material, good consistency is arranged, do the growth that the synthetic optical transfer agricultural film of light-converting agent can promote various plants, applied range with this.
We's genealogy of law is by the interchangeability by the houghite interlayer anion, quinoline is intercalation into to the houghite interlayer, quinoline has improved the asymmetry as the metal complexes of luminescence center with the metallic cation coordination formation specific group assembling structure be embedded on the houghite flaggy, thereby has improved luminous efficiency.By the kind that changes quinoline, the kind of houghite metallic cation; and the intercalation amount of quinoline; obtained the light conversion agent that can launch different colours fluorescence at visible region; due to the provide protection of houghite laminate structure, improved the thermostability of this luminescent composite simultaneously.Thereby prepare the novel photorecombination material that turns that a class different from common non-blooming houghite can be sent respective metal coordination inner complex intense fluorescence.The functionalization houghite preparation obtained by the method is simple, and easy to operate, Product Green is environment friendly and pollution-free, and particle diameter is controlled, with macromolecular material, good consistency is arranged.
Compared with prior art, advantage of the present invention is:
1. the multicolor luminous matrix material of houghite of the quinoline intercalation of preparation has greatly reduced the consumption that the quinoline metallo-chelate is directly used as light-converting agent, reduced cost, avoid the quenching of fluorescence caused due to reunion simultaneously, improved luminous efficiency and thermostability.
The multicolor luminous matrix material of houghite of the quinoline intercalation of preparation by quinoline can with the houghite laminate on the metallic cation coordination form the specific group assembling structure, and prepare a series of luminescent materials of launching different wave length fluorescence by the kind, the kind of houghite metallic cation and the intercalation amount of quinoline that change quinoline.Prepare simple, easy to operate, Product Green is environment friendly and pollution-free, particle diameter is controlled, with macromolecular material good consistency is arranged, do the growth that the synthetic optical transfer agricultural film of light-converting agent can promote various plants, applied range with this.
The accompanying drawing explanation:
Fig. 1 is the multicolor luminous matrix material utilizing emitted light of the zinc-aluminum gavite spectrogram (explanation can change the position of emission wavelength by the intercalation amount that changes oxine in zinc-aluminum gavite, with this, obtain multicolor luminous matrix material) of embodiment 1 gained oxine intercalation.
Fig. 2 is the multicolor luminous matrix material utilizing emitted light of the zinc-aluminum gavite spectrogram (explanation can change the position of emission wavelength by the intercalation amount that changes 5-sulfonic acid-oxine in zinc-aluminum gavite, with this, obtain multicolor luminous matrix material) of embodiment 2 gained 5-sulfonic acid-oxine intercalation.
Fig. 3 be embodiment 1 and embodiment 2 gained 10 groups of samples (left 1-5 group respectively in corresponding embodiment 1 oxine at 10g/L, 20g/L, 30g/L, 40g/L, the multicolor luminous matrix material of zinc-aluminum gavite of the oxine intercalation obtained under the 50g/L condition, in the corresponding embodiment 2 of right 1-5 group difference, 5-sulfonic acid-oxine is at 10g/L, 20g/L, 30g/L, 40g/L, the multicolor luminous matrix material of zinc-aluminum gavite of the 5-sulfonic acid obtained under the 50g/L condition-oxine intercalation) illuminated diagram under the 365nm UV-irradiation (in the time of can observing intuitively the intercalation amount difference of quinoline in houghite under ultra violet lamp, the aqueous solution of this matrix material can be launched the visible ray of different wave length).
The gray scale schematic diagram that Fig. 4 is Fig. 3;
Fig. 5 is that (emission wavelength is respectively 493nm and 470nm for the fluorescent exciting spectrogram of zinc-aluminum gavite luminescent composite of the 5-sulfonic acid that in the zinc-aluminum gavite luminescent composite of the oxine intercalation that in embodiment 1, oxine obtains under the 20g/L condition and embodiment 2,5-sulfonic acid-oxine obtains under the 50g/L condition-oxine intercalation.Major part by this fluorescent exciting spectrogram explanation ultraviolet region can excite this matrix material luminous).
Fig. 6 is the scanning electron microscope (SEM) photograph (can illustrate that by scanning electron microscope (SEM) photograph this luminescent composite size is little, degree of crystallinity is high, be applicable to being mixed in macromolecular material) of the zinc-aluminum gavite luminescent composite of the 5-sulfonic acid that in the zinc-aluminum gavite luminescent composite of the oxine intercalation that in embodiment 1, oxine obtains under the 20g/L condition and embodiment 2,5-sulfonic acid-oxine obtains under the 50g/L condition-oxine intercalation.
Embodiment:
Embodiment 1.
Preparation is containing the Zn (NO of 0.5mol/L
3)
2al (NO with 0.25mol/L
3)
3water solution A; Preparation is containing the NaOH aqueous solution B of 1mol/L; To pH=8, continue magneton and stir under nitrogen protection, solution B being added drop-wise to solution A slowly, obtain slurries C, rapidly slurries C is transferred in autoclave, be placed in 120 ℃ of baking ovens and react 20 hours.Reaction product is centrifugal, respectively with removing CO
2deionized water and washing with alcohol 3 times, colourless to washings, the centrifugal filter cake obtained, 60 ℃ of dryings 24 hours, is obtained to the houghite precursor.The houghite precursor of preparation is joined in the aqueous solution of oxine and reacted, houghite precursor 0.5g/L, oxine 10~50g/L in the aqueous solution, stirring velocity is 4000 rev/mins, 60 ℃ lower 24 hours, standing 10 hours, use the ethanol centrifuge washing, 60 ℃ of dryings 24 hours, obtain the multicolor luminous matrix material of zinc-aluminum gavite of oxine intercalation.When oxine concentration is 10g/L or 50g/L, the matrix material light emitting region is in the yellow-green light district of 500~600nm; When oxine concentration is 20g/L, the matrix material light emitting region is in the bluish-green coloured light district of 450~550nm.
Preparation is containing the Zn (NO of 0.5mol/L
3)
2al (NO with 0.25mol/L
3)
3water solution A; Preparation is containing the NaOH aqueous solution B of 1mol/L; To pH=8, continue magneton and stir under nitrogen protection, solution B being added drop-wise to solution A slowly, obtain slurries C, rapidly slurries C is transferred in autoclave, be placed in 120 ℃ of baking ovens and react 20 hours.Reaction product is centrifugal, respectively with removing CO
2deionized water and washing with alcohol 3 times, colourless to washings, the centrifugal filter cake obtained, 60 ℃ of dryings 24 hours, is obtained to the houghite precursor.The houghite precursor of preparation is joined in the aqueous solution of 5-sulfonic acid-oxine and reacted, houghite precursor 0.5g/L, 5-sulfonic acid-oxine 10~50g/L in the aqueous solution, stirring velocity is 4000 rev/mins, 60 ℃ lower 24 hours, standing 10 hours, use the ethanol centrifuge washing, 60 ℃ of dryings 24 hours, obtain the multicolor luminous matrix material of zinc-aluminum gavite of 5-sulfonic acid-oxine intercalation.When 5-sulfonic acid-oxine concentration is 10g/L or 30g/L, the matrix material light emitting region is in the yellowish green blue light district of 450~600nm; When 5-sulfonic acid-oxine concentration is 40g/L or 50g/L, the matrix material light emitting region is in the turquoise purple light district of 400~575nm.
Preparation is containing the ZnCl of 0.6mol/L
2ceCl with 0.25mol/L
3water solution A; Preparation is containing the NaOH aqueous solution B of 1mol/L; To pH=11, continue magneton and stir under nitrogen protection, solution B being added drop-wise to solution A slowly, obtain slurries C,, rapidly slurries C is transferred in autoclave, be placed in 130 ℃ of baking ovens and react 40 hours.Reaction product is centrifugal, respectively with removing CO
2deionized water and washing with alcohol 3 times, colourless to washings, the centrifugal filter cake obtained, 40 ℃ of dryings 24 hours, is obtained to the houghite precursor.The houghite precursor of preparation is joined in the aqueous solution of 4-methyl-oxine and reacted, houghite precursor 0.5g/L, 4-methyl-oxine 10~50g/L in the aqueous solution, stirring velocity is 3000 rev/mins, 35 ℃ lower 24 hours, standing 10 hours, use the ethanol centrifuge washing, 40 ℃ of dryings 24 hours, obtain the multicolor luminous matrix material of zinc cerium houghite of 4-methyl-oxine intercalation.When 4-methyl-oxine concentration is 10g/L, the matrix material light emitting region is in the yellow-green light district of 500~600nm; When 4-methyl-oxine concentration is 25g/L, the matrix material light emitting region is in the blood orange coloured light district of 550~620nm.
Embodiment 4.
Preparation is containing the CoCl of 1mol/L
2alCl with 0.3mol/L
3water solution A; Preparation is containing the NaOH aqueous solution B of 1mol/L; To pH=9, continue magneton and stir under nitrogen protection, solution B being added drop-wise to solution A slowly, obtain slurries C, rapidly slurries C is transferred in autoclave, be placed in 150 ℃ of baking ovens and react 20 hours.Reaction product is centrifugal, respectively with removing CO
2deionized water and washing with alcohol 3 times, colourless to washings, the centrifugal filter cake obtained, 60 ℃ of dryings 24 hours, is obtained to the houghite precursor.The houghite precursor of preparation is joined in the aqueous solution of 5-nitro-oxine and reacted, houghite precursor 0.5g/L, 5-nitro-oxine 10~50g/L in the aqueous solution, stirring velocity is 4000 rev/mins, 60 ℃ lower 24 hours, standing 10 hours, use the ethanol centrifuge washing, 60 ℃ of dryings 24 hours, obtain the multicolor luminous matrix material of cobalt aluminium houghite of 5-nitro-oxine intercalation.When 5-nitro-oxine concentration is 30g/L, the matrix material light emitting region is in the blue light district of 440~500nm; When 5-nitro-oxine concentration is 45g/L, the matrix material light emitting region is in the orange coloured light district of 570~600nm; When 5-nitro-oxine concentration is 50g/L, the matrix material light emitting region is in the yellowish green blue light district of 440~600nm.
Embodiment 5.
Preparation is containing the Cu (NO of 0.5mol/L
3)
2fe (NO with 0.25mol/L
3)
3water solution A; Preparation is containing the NaOH aqueous solution B of 1mol/L; To pH=10, continue magneton and stir under nitrogen protection, solution B being added drop-wise to solution A slowly, obtain slurries C, rapidly slurries C is transferred in autoclave, be placed in 120 ℃ of baking ovens and react 30 hours.Reaction product is centrifugal, respectively with removing CO
2deionized water and washing with alcohol 3 times, colourless to washings, the centrifugal filter cake obtained, 60 ℃ of dryings 24 hours, is obtained to the houghite precursor.The houghite precursor of preparation is joined in the aqueous solution of 5-sulfonic acid-oxine and reacted, houghite precursor 0.5g/L, 5-sulfonic acid-oxine 10~50g/L in the aqueous solution, stirring velocity is 4000 rev/mins, 60 ℃ lower 24 hours, standing 10 hours, use the ethanol centrifuge washing, 60 ℃ of dryings 24 hours, obtain the multicolor luminous matrix material of copper iron houghite of 5-sulfonic acid-oxine intercalation.When 5-sulfonic acid-oxine concentration is 10g/L, the matrix material light emitting region is in the green light district of 500~550nm; When 5-sulfonic acid-oxine concentration is 35g/L, the matrix material light emitting region is in the blood orange coloured light district of 570~640nm; When 5-sulfonic acid-oxine concentration is 50g/L, the matrix material light emitting region is in the yellowish green blue light district of 440~600nm.
Embodiment 6
Preparation is containing the Zn (NO of 0.75mol/L
3)
2eu (NO with 0.25mol/L
3)
3water solution A; Preparation is containing the NaOH aqueous solution B of 1mol/L; To pH=10, continue magneton and stir under nitrogen protection, solution B being added drop-wise to solution A slowly, obtain slurries C, rapidly slurries C is transferred in autoclave, be placed in 120 ℃ of baking ovens and react 50 hours.Reaction product is centrifugal, respectively with removing CO
2deionized water and washing with alcohol 3 times, colourless to washings, the centrifugal filter cake obtained, 45 ℃ of dryings 24 hours, is obtained to the houghite precursor.The houghite precursor of preparation is joined in the aqueous solution of 5-nitro-oxine and reacted, houghite precursor 0.5g/L, 5-nitro-oxine 10~50g/L in the aqueous solution, stirring velocity is 4000 rev/mins, 60 ℃ lower 24 hours, standing 10 hours, use the ethanol centrifuge washing, 45 ℃ of dryings 24 hours, obtain the zinc europium houghite luminescent composite of 5-nitro-oxine intercalation.When 5-nitro-oxine concentration is 15g/L, the matrix material light emitting region is in the bluish-green coloured light district of 400~550nm; When 5-nitro-oxine concentration is 35g/L, the matrix material light emitting region is in the yellow-green light district of 500~600nm.
This paper has enumerated 6 case study on implementation principle of the present invention and implementation method has been set forth, and the explanation of above case study on implementation can be used to help to understand principle of the present invention and method.But above case study on implementation is not unique, should not be construed as limitation of the present invention.Simultaneously, for one of ordinary skill in the art, according to the principle of the invention and method, can change flexibly in specific embodiments and applications.
Claims (1)
1. the multicolor luminous material of the houghite of a quinoline intercalation is characterized in that making by following steps:
1) by the standby interlayer anion of hydro-thermal legal system, be Cl-or NO
3 2-, laminate divalence, trivalent metal cation mol ratio M
2+/ M
3+=2.0~4.0, M wherein
2+the concentration houghite precursor that is 0.2~1.0mol/L;
2) the houghite precursor prepared by step 1) joins in the aqueous solution of quinoline and is reacted, houghite precursor 0.5g/L, quinoline 10~50g/L in the aqueous solution, stirring velocity is 2000~4000 rev/mins, under 30~60 ℃, react 12~24 hours, standing 10~20 hours, use the ethanol centrifuge washing, 30~60 ℃ of dryings 12~24 hours, obtain the multicolor luminous matrix material of houghite of quinoline intercalation;
Described divalent metal M
2+for Fe
2+, Co
2+, Cu
2+, Zn
2+, Mn
2+, Ca
2+, Mg
2+or Ni
2+; Described trivalent metal cation M
3+for Al
3+, Cr
3+, Mn
3+, Fe
3+, Ce
3+, Eu
3+or Sm
3+;
Described quinoline is oxine, 2,6-dihydroxyl quinoline, 4,8-dihydroxyl quinaldic acid, HQS, 5-nitro-oxine, 4-methyl-oxine or 2,4-dihydroxyl quinoline.
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CN106589219A (en) * | 2016-12-16 | 2017-04-26 | 咸阳师范学院 | Preparation method for fluorescent hydrotalcite/acrylic resin composite material |
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CN104327845A (en) * | 2014-11-17 | 2015-02-04 | 京东方科技集团股份有限公司 | Blue light polarizing thin film and preparation method thereof as well as blue light backlight source and liquid crystal display device |
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WO2016078220A1 (en) * | 2014-11-17 | 2016-05-26 | 京东方科技集团股份有限公司 | Blue light polarizing thin film and preparation method therefor, as well as blue light backlight source and liquid crystal display device |
CN106589219A (en) * | 2016-12-16 | 2017-04-26 | 咸阳师范学院 | Preparation method for fluorescent hydrotalcite/acrylic resin composite material |
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