CN103554142A - Preparation method of nucleotide-rare earth coordination polymer light-emitting material - Google Patents
Preparation method of nucleotide-rare earth coordination polymer light-emitting material Download PDFInfo
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- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 239000013256 coordination polymer Substances 0.000 title claims abstract description 28
- 229920001795 coordination polymer Polymers 0.000 title claims abstract description 28
- 239000000463 material Substances 0.000 title claims abstract description 23
- -1 rare earth ions Chemical class 0.000 claims abstract description 33
- 239000002773 nucleotide Substances 0.000 claims abstract description 23
- 150000002910 rare earth metals Chemical class 0.000 claims abstract description 16
- 125000003729 nucleotide group Chemical group 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 claims description 19
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 238000013016 damping Methods 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 12
- 238000005119 centrifugation Methods 0.000 claims description 11
- 238000001556 precipitation Methods 0.000 claims description 11
- 239000008367 deionised water Substances 0.000 claims description 9
- 229910021641 deionized water Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052771 Terbium Inorganic materials 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
- 238000013019 agitation Methods 0.000 claims description 5
- 229910052693 Europium Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000009736 wetting Methods 0.000 claims description 4
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011540 sensing material Substances 0.000 claims description 2
- 239000003446 ligand Substances 0.000 abstract description 28
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- 238000003384 imaging method Methods 0.000 abstract description 2
- 238000012377 drug delivery Methods 0.000 abstract 1
- 239000000700 radioactive tracer Substances 0.000 abstract 1
- 230000010148 water-pollination Effects 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 28
- 238000004458 analytical method Methods 0.000 description 9
- 230000005540 biological transmission Effects 0.000 description 6
- 238000002189 fluorescence spectrum Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 4
- 238000001027 hydrothermal synthesis Methods 0.000 description 4
- 239000002086 nanomaterial Substances 0.000 description 4
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- 239000007995 HEPES buffer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000013329 compounding Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YCGAZNXXGKTASZ-UHFFFAOYSA-N thiophene-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)S1 YCGAZNXXGKTASZ-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to a preparation method of a nucleotide-rare earth coordination polymer light-emitting material. According to the method, a hydrophilic light-emitting rare earth coordination polymer material is prepared from biomolecules including nucleotide, rare earth ions and micromolecule ligands through molecular self-assembling. According to the preparation method, because biomolecules are used as components, the prepared nucleotide-rare earth coordination polymer light-emitting material not only has a high light-emitting intensity, but also has good biocompatibility and hydrophily; through adoption of molecular self-assembling for preparation, the reaction is performed at room temperature and the conditions of a high temperature and a long reaction time, required by usual preparation, are not needed; therefore, the method is simple and easy to operate. The prepared light-emitting material has a good application prospect on the aspects of molecular sensing, tracer imaging, drug delivery, and the like.
Description
Technical field
The present invention relates to a kind of preparation method of Nucleotide rare earth coordination polymer luminescent material, the Nucleotide rare earth coordination polymer luminescent material of preparation can be used for sensing, mark and the imaging of molecular/ionic, belongs to rare earth luminous field of nano material preparation.
Background technology
Fluorescence technique has application very widely in fields such as life science, medical science, food safety, environment protection.Various organic dye molecules are mainly used in traditional fluorometric analysis, and because excitation wavelength and the emission wavelength of organic dye molecule are close, Stokes displacement little (20-30nm), is easily subject to the interference of exciting light during detection; Also easily there is photobleaching and quenching effect in organic dye molecule, causes fluorescence intensity to reduce.In addition, the fluorometric analysis of fluorometric analysis, especially biological sample, the scope (350-600nm) of the most of dye molecule emmission spectrum of background fluorescence nearly cover, will produce nonspecific fluorescence interference, and these deficiencies have limited many application of fluorometric analysis.
The fluorescence of rare earth ion has large Stocks displacement, narrow emission peak, long fluorescence lifetime, long fluorescence lifetime allows time resolved fluorescence analysis, pass through delay measurements, the background fluorescence of the short fluorescence lifetime that can fully decay and various non-specific fluorescence, obtain the signal to noise ratio higher than conventional fluorometric analysis.Fluorescence based on rare earth ion has been widely used in various fluorometric analyses.At present, rare earth ion fluorometric analysis is mainly to utilize rare earth compounding molecule, and luminous rare earth compounding often needs the synthetic luminous part with special construction, and the synthetic of these parts is complicated and expensive.
Solid-state rare earth coordination polymer luminescent material has enriched Fluorimetric Analysis of Rare, rare earth coordination polymer has been reported as luminescent material or for fluorometric analysis, China Patent Publication No. CN102276637A, 2011, Fan Ruiqing, Zhang Huijie, Yang Yulin, terbium ligand polymer and synthetic method thereof and application, disclose and a kind ofly take biphenyl dicarboxylic acid as part, by 165 ℃ of methods of preparing the luminous ligand polymer of terbium of hydro-thermal reaction; China Patent Publication No. CN102745765A, 2012, Feng Xun, horse is peaceful, Liu Lang, Wang Liya, Shi Zhiqiang, Song Hongliang, Zn-Tb ligand polymer luminescent material based on amino acid part and preparation method thereof, discloses a kind ofly with glyoxal ethyline-4, and 5-dicarboxylic acid is part, in conjunction with terbium and zine ion, by hydro-thermal reaction, prepare the method for luminous ligand polymer; China Patent Publication No. CN102079752A, 2010, Sun Yaguang; Jiang Bing, has the synthesis method of rare-earth coordination polymer of calcium ion fluorescent probe function, discloses a kind ofly to take 2,5-ThiophenedicarboxyliAcid Acid as part, prepares the method for terbium ligand polymer by hydrothermal method; China Patent Publication No. CN101101291A, 2007, Zhao Bin, Chen Zhi, three-D nano hole Eu coordinate polymer type zinc ion fluorescent probe and preparation method thereof and application, disclose a kind of europium ligand polymer that is part with 2,5-thiophene dicarboxylic acid, for Zn
2+detection.Different from the preparation method of report, the present invention utilizes the self-assembly characteristic of biomolecules, with biomolecules Nucleotide and rare earth ion, prepares rare earth coordination polymer luminescent material, there is not yet report both at home and abroad.
The deficiency that prior art exists: the preparation of the rare earth coordination polymer of having reported is mainly by hydro-thermal reaction, and temperature of reaction is more than 100 ℃, and the reaction times reaches tens hours to several days, what have also needs further high temperature sintering; The rare earth coordination polymer of preparation mainly consists of organic ligand, and wetting ability and the biocompatibility of rare earth coordination polymer are poor, are mostly used in organic solvent.
Summary of the invention
Technical problem: the object of this invention is to provide a kind of preparation method of Nucleotide rare earth coordination polymer luminescent material, the method had both had high luminous intensity and excellent hydrophilic and biocompatibility, can at room temperature prepare rare earth coordination polymer again fast.
Technical scheme: the preparation method of a kind of Nucleotide rare earth coordination polymer luminescent material of the present invention, utilize biomolecules Nucleotide, rare earth ion and luminous part to generate rare earth coordination polymer luminescent material by molecular self-assembling, this Nucleotide coordination polymer luminescent material has the fluorescence of strong rare earth ion, there is good biocompatibility and wetting ability simultaneously, as various luminous spikes or sensing material, concrete steps are:
The first step, is dissolved in biomolecules Nucleotide in N-2-hydroxyethyl piperazine-N'-2-ethyl sulfonic acid damping fluid, and the pH scope control of this damping fluid is at 6.5-8.0;
Second step, by the molar ratio that forms title complex, add respectively the aqueous solution of rare earth ion and the aqueous solution of luminous part in above-mentioned damping fluid, fully mix, solution under agitation reacts 2-3 hour, centrifugation, gained precipitation is by method deionized water wash 3-5 time of centrifugation, dry rear standby in 60-70 ℃ of baking oven.
Wherein:
The biomolecules Nucleotide using is AMP AMP or adenosine diphosphate (ADP) ADP.
The rare earth ion using is terbium ion (Tb
3+) or europium ion (Eu
3+).
The luminous part using is 2, a kind of in dipicolimic acid 2, tsiklomitsin or phenanthroline.
Beneficial effect: the raw material that the present invention uses can easily obtain from commercial channel, low price, has avoided the complexity of common organic light emission part synthetic; Owing to utilizing the self-assembling reaction of biomolecules, preparation feedback at room temperature carries out, and without high temperature and long reaction times, method is easy, easily operates and grasps; Prepared rare earth coordination polymer not only luminous intensity is high, and owing to containing biomolecules Nucleotide, wetting ability and good biocompatibility, be applicable to the application in living things system.
Accompanying drawing explanation
Fig. 1. the transmission electron microscope picture of AMP-terbium-pyridine dicarboxylic acid (AMP-Tb-DPA) ligand polymer.
Fig. 2. AMP-terbium-pyridine dicarboxylic acid (AMP-Tb-DPA) ligand polymer in the aqueous solution (0.5%, fluorescence spectrum figure w/w).
Fig. 3. the transmission electron microscope picture of AMP-europium-tsiklomitsin (AMP-Eu-Tc) ligand polymer.
Fig. 4. AMP-europium-tsiklomitsin (AMP-Eu-Tc) ligand polymer in the aqueous solution (0.5%, fluorescence spectrum figure w/w).
Fig. 5. the transmission electron microscope picture of adenosine diphosphate (ADP)-terbium-phenanthroline (ADP-Tb-Phen) ligand polymer.
Fig. 6. adenosine diphosphate (ADP)-terbium-phenanthroline (ADP-Tb-Phen) ligand polymer in the aqueous solution (0.5%, fluorescence spectrum figure w/w).
Embodiment
The preparation method's of a kind of Nucleotide rare earth coordination polymer luminescent material of the present invention step is:
The first step, is dissolved in biomolecules Nucleotide in N-2-hydroxyethyl piperazine-N'-2-ethyl sulfonic acid damping fluid, and the pH scope control of damping fluid is at 6.5-8.0;
Second step, by the molar ratio by forming title complex, add respectively the aqueous solution of rare earth ion and the aqueous solution of luminous part in above-mentioned damping fluid, fully mix, solution under agitation reacts 2-3 hour, centrifugation, gained precipitation is by method deionized water wash 3-5 time of centrifugation, dry rear standby in 60-70 ℃ of baking oven.
Embodiment 1: the preparation of AMP-terbium-pyridine dicarboxylic acid (AMP-Tb-DPA) ligand polymer
In 0.5mL N-2-hydroxyethyl piperazine-N'-2-ethyl sulfonic acid (HEPES) damping fluid (100mM, pH7.4) that contains 10mM AMP (AMP), adding 0.5mL concentration is the Tb (NO of 10mM
3)
3pyridine dicarboxylic acid (DPA) aqueous solution that the aqueous solution and 0.5mL concentration are 10mM, produce white precipitation, solution under agitation continues to react 3 hours, centrifugation (6000rpm * 10min) collecting precipitation, the washing of gained precipitate with deionized water, centrifugation, deionized water wash in triplicate, finally, precipitation is placed in to 70 ℃ of baking ovens dry, after being dried, is stored in moisture eliminator standby.
Fig. 1 is the transmission electron microscope picture of AMP-terbium-pyridine dicarboxylic acid (AMP-Tb-DPA) ligand polymer of preparation, and ligand polymer shows network nano structure.Fig. 2 be AMP-terbium-pyridine dicarboxylic acid (AMP-Tb-DPA) ligand polymer in the aqueous solution (0.5%, fluorescence spectrum figure w/w), at 490nm, 545nm, the emission peak of 584nm and 621nm is typical terbium ion (Tb
3+) emission peak, and do not comprise comparing of pyridine dicarboxylic acid, the luminous intensity of AMP-Tb-DPA ligand polymer has strengthened approximately 10 times.
Embodiment 2: the preparation of AMP-europium-tsiklomitsin (AMP-Eu-Tc) ligand polymer
In 2mL N-2-hydroxyethyl piperazine-N'-2-ethyl sulfonic acid (HEPES) damping fluid (100mM, pH7.4) that contains 10mM AMP (AMP), adding 1.5mL concentration is the Eu (NO of 10mM
3)
3tsiklomitsin (Tc) aqueous solution that the aqueous solution and 0.5mL concentration are 10mM, produce white precipitation, solution under agitation continues to react 3 hours, centrifugation (14000rpm * 10min) collecting precipitation, the washing of gained precipitate with deionized water, centrifugation, deionized water wash in triplicate, finally, precipitation is placed in to 70 ℃ of baking ovens dry, after being dried, is stored in moisture eliminator standby.
Fig. 3 is the transmission electron microscope picture of AMP-europium-tsiklomitsin (AMP-Eu-Tc) ligand polymer of preparation, and ligand polymer shows network nano structure.Fig. 4 is that in the aqueous solution, (0.5%, fluorescence spectrum figure w/w), is typical europium ion (Eu at the emission peak of 594nm and 616nm to AMP-europium-tsiklomitsin (AMP-Eu-Tc) ligand polymer
3+) emission peak; With do not comprise comparing of tsiklomitsin, the luminous intensity of AMP-Eu-Tc ligand polymer significantly strengthens.
Embodiment 3: the preparation of adenosine diphosphate (ADP)-terbium-phenanthroline (ADP-Tb-Phen) ligand polymer
In 1mL N-2-hydroxyethyl piperazine-N'-2-ethyl sulfonic acid (HEPES) damping fluid (100mM, pH7.4) that contains 3mM adenosine diphosphate (ADP) (ADP), add the Tb (NO that 1 mL concentration is 3mM
3)
3the aqueous solution, adding 2mL concentration is the aqueous solution of the phenanthroline (Phen) of 1.5mM again, under this mixing solutions room temperature, stir 3h, the centrifugal 20min collecting precipitation of 10000rpm, unreacted reagent, centrifugation are removed in the washing of gained precipitate with deionized water, deionized water wash in triplicate, finally, precipitation is placed in to 70 ℃ of baking ovens dry, after being dried, is stored in moisture eliminator standby.
Fig. 5 is the transmission electron microscope picture of adenosine diphosphate (ADP)-terbium-phenanthroline (ADP-Tb-Phen) ligand polymer of preparation, and ligand polymer shows network nano structure.Fig. 6 be adenosine diphosphate (ADP)-terbium-phenanthroline (ADP-Tb-Phen) ligand polymer in the aqueous solution (0.5%, fluorescence spectrum figure w/w), at 490nm, 545nm, the emission peak of 584nm and 621nm is typical terbium ion (Tb
3+) emission peak, and do not comprise comparing of phenanthroline, the luminous intensity of ADP-Tb-Phen ligand polymer has strengthened approximately 20 times.
Other Nucleotide is identical with above-mentioned condition with the preparation condition of the rare earth coordination polymer that rare earth ion forms, and the result obtaining is also similar.
Claims (4)
1. the preparation method of a Nucleotide rare earth coordination polymer luminescent material, it is characterized in that utilizing biomolecules Nucleotide, rare earth ion and luminous part to generate rare earth coordination polymer luminescent material by molecular self-assembling, this Nucleotide coordination polymer luminescent material has the fluorescence of strong rare earth ion, there is good biocompatibility and wetting ability simultaneously, as various luminous spikes or sensing material, concrete steps are:
The first step, is dissolved in biomolecules Nucleotide in N-2-hydroxyethyl piperazine-N'-2-ethyl sulfonic acid damping fluid, and the pH scope control of this damping fluid is at 6.5-8.0;
Second step, by the molar ratio that forms title complex, add respectively the aqueous solution of rare earth ion and the aqueous solution of luminous part in above-mentioned damping fluid, fully mix, solution under agitation reacts 2-3 hour, centrifugation, gained precipitation is by method deionized water wash 3-5 time of centrifugation, dry rear standby in 60-70 ℃ of baking oven.
2. the preparation method of Nucleotide rare earth coordination polymer luminescent material according to claim 1, is characterized in that the biomolecules Nucleotide using is AMP AMP or adenosine diphosphate (ADP) ADP.
3. the rare earth ion that the preparation method of Nucleotide rare earth coordination polymer luminescent material according to claim 1 uses is terbium ion (Tb
3+) or europium ion (Eu
3+).
4. the preparation method of Nucleotide rare earth coordination polymer luminescent material according to claim 1, is characterized in that the luminous part using is 2, a kind of in dipicolimic acid 2, tsiklomitsin or phenanthroline.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103910765A (en) * | 2014-03-17 | 2014-07-09 | 东南大学 | A preparation method of a silver-ion-reinforced rare earth coordination polymer luminescent material |
| CN104803464A (en) * | 2015-05-07 | 2015-07-29 | 东南大学 | Nitrite ion scavenging agent in solution and preparation method and application thereof |
| CN104945424A (en) * | 2015-06-17 | 2015-09-30 | 江西师范大学 | Preparation method and application of rare earth coordination polymer nanoparticles |
| CN105949473A (en) * | 2016-05-16 | 2016-09-21 | 南昌大学 | Preparation method of rare-earth coordination polymer fluorescence probe and application of rare-earth coordination polymer fluorescence probe in H2O2 and glucose detection |
| CN106883421A (en) * | 2017-02-20 | 2017-06-23 | 商丘师范学院 | It is suitable to launch rare earth coordination polymer fluorescent material of white light and preparation method thereof |
| CN107057083A (en) * | 2017-05-18 | 2017-08-18 | 洛阳师范学院 | A kind of micropore terbium coordination polymer fluorescence identifying material and preparation method |
| CN111808295A (en) * | 2020-08-06 | 2020-10-23 | 西华师范大学 | Double-ligand europium-based metal organic framework material and preparation method and application thereof |
| CN115010729A (en) * | 2022-06-21 | 2022-09-06 | 南通大学 | Rare earth fluorescent material with aggregation-induced emission effect and preparation method and application thereof |
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| CN104803464A (en) * | 2015-05-07 | 2015-07-29 | 东南大学 | Nitrite ion scavenging agent in solution and preparation method and application thereof |
| CN104803464B (en) * | 2015-05-07 | 2017-03-08 | 东南大学 | A kind of solution Nitrite ion scavenger and its preparation method and application |
| CN104945424B (en) * | 2015-06-17 | 2019-10-08 | 江西师范大学 | Preparation method and application of rare earth coordination polymer nanoparticles |
| CN104945424A (en) * | 2015-06-17 | 2015-09-30 | 江西师范大学 | Preparation method and application of rare earth coordination polymer nanoparticles |
| CN105949473A (en) * | 2016-05-16 | 2016-09-21 | 南昌大学 | Preparation method of rare-earth coordination polymer fluorescence probe and application of rare-earth coordination polymer fluorescence probe in H2O2 and glucose detection |
| CN105949473B (en) * | 2016-05-16 | 2018-12-25 | 南昌大学 | The preparation method and its H of rare earth coordination polymer fluorescence probe2O2With glucose detection application |
| CN106883421B (en) * | 2017-02-20 | 2019-08-30 | 商丘师范学院 | Suitable for emitting the rare earth coordination polymer fluorescent powder and preparation method thereof of white light |
| CN106883421A (en) * | 2017-02-20 | 2017-06-23 | 商丘师范学院 | It is suitable to launch rare earth coordination polymer fluorescent material of white light and preparation method thereof |
| CN107057083A (en) * | 2017-05-18 | 2017-08-18 | 洛阳师范学院 | A kind of micropore terbium coordination polymer fluorescence identifying material and preparation method |
| CN111808295A (en) * | 2020-08-06 | 2020-10-23 | 西华师范大学 | Double-ligand europium-based metal organic framework material and preparation method and application thereof |
| CN111808295B (en) * | 2020-08-06 | 2021-11-02 | 西华师范大学 | Double-ligand europium-based metal organic framework material and preparation method and application thereof |
| CN115010729A (en) * | 2022-06-21 | 2022-09-06 | 南通大学 | Rare earth fluorescent material with aggregation-induced emission effect and preparation method and application thereof |
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