CN109400899B - Lead coordination polymer and preparation method and application thereof - Google Patents
Lead coordination polymer and preparation method and application thereof Download PDFInfo
- Publication number
- CN109400899B CN109400899B CN201811253327.4A CN201811253327A CN109400899B CN 109400899 B CN109400899 B CN 109400899B CN 201811253327 A CN201811253327 A CN 201811253327A CN 109400899 B CN109400899 B CN 109400899B
- Authority
- CN
- China
- Prior art keywords
- lead
- coordination polymer
- benzothiadiazole
- diyl
- dibenzoic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
The invention discloses a lead coordination polymer and a preparation method and application thereof, belonging to the technical field of complex preparation. The lead coordination polymer is prepared by taking (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) as a ligand and Pb2+The soluble salt is prepared by reaction; the lead coordination polymer has the chemical formula: [ Pb (L) (DMF)]n, the repeating unit containing one Pb2+A (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) anion, and a coordinating DMF molecule. Experimental results show that the lead coordination polymer prepared by the method has good fluorescence performance and thermal stability, and has important application value in the fields of color displays, fluorescent marks and the like.
Description
Technical Field
The invention belongs to the technical field of complex preparation, and particularly relates to a lead coordination polymer and a preparation method and application thereof.
Background
The traditional organic fluorescent luminescent materials have various varieties, and are provided with conjugated heterocycles and various chromophores, the structures of which are easy to adjust, and the conjugated lengths of the materials are changed by introducing unsaturated groups such as olefinic bonds, benzene rings and the like and various chromophores, so that the photoelectric properties of the compounds are changed. Such as oxadiazole and derivatives thereof, triazole and derivatives thereof, rhodamine and derivatives thereof, coumarin derivatives, 1, 8-naphthalimide derivatives, pyrazoline derivatives, triphenylamine derivatives, porphyrin compounds, carbazole, pyrazine, thiazole derivatives, perylene derivatives and the like. They are widely used in the fields of optical electronic devices, DNA diagnosis, photochemical sensors, dyes, fluorescent whitening agents, fluorescent paints, laser dyes, organic electroluminescent devices (ELDs) and the like. However, the small molecule luminescent material is easy to generate fluorescence quenching phenomenon in solid state, and devices manufactured by common doping methods are easy to aggregate and crystallize, so that the service life of the devices is reduced. Therefore, a great deal of researchers are dedicated to search for luminescent materials with better performance, and fluorescent coordination polymer luminescent materials are produced.
As a novel fluorescent probe material, the fluorescent coordination polymer has very superior physical and chemical properties compared with the traditional organic fluorescent probe material, such as good fluorescent stability, low cytotoxicity, good biocompatibility and the like. Therefore, the novel fluorescent coordination polymer fluorescent material has huge application potential and good development prospect in analytical chemistry, biomedicine, catalysis and magnetism.
However, the following problems exist in the practical application of the common coordination polymer fluorescent probe: 1. rare earth metals are mostly used, and the raw materials are expensive, so that the cost is increased, and the synthesis conditions are complex; 2. the structure has poor thermal stability due to the influence of ligands and metals; 3. low yield and poor solubility.
Disclosure of Invention
The invention aims to provide a lead coordination polymer, a preparation method and application thereof, and solves the problems of high cost, poor thermal stability and low yield of the existing fluorescent coordination polymer.
The invention is realized by the following technical scheme:
a lead coordination polymer having the formula: [ Pb (L) (DMF) n, n is a positive integer; l is (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) anion and DMF is N, N-dimethylformamide.
Further, the lead coordination polymer is monoclinic system, space group is P2(1)/n, unit cell parameter is
β＝93.805(3)°；
Z＝4。
Further, the Pb-O bond is grown at
In the meantime.
Further, the repeating unit of the lead coordination polymer contains one Pb2+，Pb2+Using an octadentate coordination mode, Pb2+Respectively with seven carboxyl oxygen atoms from five different (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligands and one DMF oxygen atom.
Further, (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) adopts monodentate and chelate coordination modes.
The invention also discloses a preparation method of the lead coordination polymer, which comprises the following steps:
1) according to (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid), Pb2+The dosage ratio of the soluble salt to the N, N-dimethylformamide solution is 0.1 mmol: 0.2 mmol: 10mL of (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid), Pb2+And N, N-dimethylformamide solution;
2) dissolving (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligand with pH of 4 in N, N-dimethylformamide solution to prepare mixed solution, and adding Pb2+Adding the soluble salt of (a) into the mixed solution;
3) and (3) under a sealed condition, carrying out constant temperature treatment at 120-160 ℃ for 24-72 h, then slowly cooling to room temperature, filtering, and washing to obtain a yellow needle crystal, namely the lead coordination polymer.
Further, Pb2+The soluble salt of (A) is lead nitrate, lead sulfate or lead chloride.
Further, the washing is with fresh DMF solvent.
Further, nitric acid, sulfuric acid, or hydrochloric acid was added dropwise to the (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligand to adjust the pH of the ligand to 4.
The invention also discloses application of the lead coordination polymer as a fluorescent material in preparation of LED lamps, colored lamps or colored displays.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention discloses a lead coordination polymer, which takes (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) as a ligand and Pb2+The repeating unit of the coordination polymer contains one Pb2+A (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) anion, and a coordinating DMF molecule. The material has the advantages of simple synthesis method, low cost, little pollution, good thermal stability, capability of emitting clear yellow fluorescence and pure color. The polymer has good fluorescence property and quite strong luminous intensity, can be used as a fluorescent material, and has important application value in the fields of color displays, fluorescent marks and the like.
The invention discloses a preparation method of a lead coordination polymer, which comprises the steps of firstly dissolving (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) in N, N-dimethylformamide solution, and then adding Pb2+The lead coordination polymer is finally obtained by sealing reaction of the soluble salt, the method is a simple and efficient synthesis method, the process is simple, the cost is low, and the polymer has yellow green fluorescence at 517nm and good performance as shown by a fluorescence spectrometer test at room temperature.
Drawings
FIG. 1 is a structural view of an asymmetric unit of the lead coordination polymer of the present invention;
FIG. 2 is a structural diagram showing a coordination mode of a lead coordination polymer of the present invention;
FIG. 3 is a two-dimensional structural drawing of a lead coordination polymer of the present invention;
FIG. 4 is a powder diffraction pattern of the lead coordination polymer of the present invention; as synthesized represents the measured result of polymer experiment, and simulated represents the result of single crystal simulation;
FIG. 5 is a thermogravimetric analysis of a lead coordination polymer of the present invention;
FIG. 6 is a fluorescence spectrum of a lead coordination polymer of the present invention; wherein the abscissa is wavelength, the ordinate is intensity, ex is emitted light, em is excitation light;
FIG. 7 is a CIE diagram of a lead coordination polymer of the invention with a ligand.
Detailed Description
The present invention will now be described in further detail with reference to specific examples, which are intended to be illustrative, but not limiting, of the invention.
Example 1
A method for preparing a lead coordination polymer, comprising the steps of:
1) taking 0.1mmol of (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligand, slowly dropwise adding nitric acid into the ligand to enable the pH value of the ligand to be 4, dissolving the adjusted ligand into 10mL of N, N-dimethylformamide solution to prepare a mixed solution, and transferring the mixed solution into a reaction kettle; weighing 0.2mmol of lead nitrate, and adding the lead nitrate into the mixed solution;
2) sealing the reaction kettle, carrying out constant temperature treatment at 120 ℃ for 48h, and then slowly cooling to room temperature;
3) and then filtering the solution, and washing the solution by using an N, N-dimethylformamide solution to obtain a yellow needle crystal, namely the lead coordination polymer.
A polytetrafluoroethylene lined hydrothermal reaction vessel having a volume of 20mL is generally used.
Example 2
1) Taking 0.2mmol of (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligand, slowly dropwise adding nitric acid into the ligand to enable the pH value of the ligand to be 4, dissolving the adjusted ligand into 20mL of N, N-dimethylformamide solution to prepare a mixed solution, and transferring the mixed solution into a reaction kettle; weighing 0.4mmol of lead nitrate, and adding the lead nitrate into the mixed solution;
2) sealing the reaction kettle, carrying out constant temperature treatment at 120 ℃ for 48h, and then slowly cooling to room temperature;
3) and then filtering the solution, and washing the solution by using an N, N-dimethylformamide solution to obtain a yellow needle crystal, namely the lead coordination polymer.
Examples 1 to 2 (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) was used as a ligand, and a lead nitrate was used to obtain a lead coordination polymer by a hydrothermal method, which was yellow needle-like crystal in appearance, odorless, and insoluble in organic solvents and water. Has the advantages of simple process, low cost, good repeatability and the like.
Example 3
1) Taking 0.1mmol of (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligand, slowly dropwise adding sulfuric acid into the ligand to enable the pH value of the ligand to be 4, then dissolving the adjusted ligand into 10mL of N, N-dimethylformamide solution to prepare a mixed solution, and transferring the mixed solution into a reaction kettle; weighing 0.2mmol of lead sulfate, and adding the lead sulfate into the mixed solution;
2) sealing the reaction kettle, carrying out constant temperature treatment at 120 ℃ for 48h, and then slowly cooling to room temperature;
3) and then filtering the solution, and washing the solution by using an N, N-dimethylformamide solution to obtain a yellow needle crystal, namely the lead coordination polymer.
In the embodiment, a coordination polymer of lead is obtained by using (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) as a ligand and lead sulfate through a hydrothermal method, and the coordination polymer is yellow needle-shaped crystals in appearance, is odorless and is insoluble in organic solvents and water.
Example 4
1) Taking 0.1mmol of (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligand, slowly dropwise adding hydrochloric acid into the ligand to enable the pH value of the ligand to be 4, dissolving the adjusted ligand into 10mL of N, N-dimethylformamide solution to prepare a mixed solution, and transferring the mixed solution into a reaction kettle; weighing 0.2mmol of lead chloride, and adding the lead chloride into the mixed solution;
2) sealing the reaction kettle, carrying out constant temperature treatment at 120 ℃ for 48h, and then slowly cooling to room temperature;
3) and then filtering the solution, and washing the solution by using an N, N-dimethylformamide solution to obtain a yellow needle crystal, namely the lead coordination polymer.
Example 5
1) Taking 0.3mmol of (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligand, slowly dropwise adding hydrochloric acid into the ligand to enable the pH value of the ligand to be 4, dissolving the adjusted ligand into 30mL of N, N-dimethylformamide solution to prepare a mixed solution, and transferring the mixed solution into a reaction kettle; weighing 0.6mmol of lead chloride, and adding the lead chloride into the mixed solution;
2) sealing the reaction kettle, carrying out constant temperature treatment at 120 ℃ for 48h, and then slowly cooling to room temperature;
3) and then filtering the solution, and washing the solution by using an N, N-dimethylformamide solution to obtain a yellow needle crystal, namely the lead coordination polymer.
Examples 4 to 5 lead coordination polymers were obtained by hydrothermal method using (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) as a ligand and lead chloride, and were yellow needle-like crystals in appearance, odorless, and insoluble in organic solvents and water.
The lead coordination polymer prepared by the invention is a linear diacid porous fluorescent coordination polymer, and has the chemical formula: [ Pb (L) (DMF)]nAnd n is a positive integer.
The prepared lead coordination polymer crystal is monochromized by a graphite monochromator on a Bruker APEX-II CCD diffractometer
Rays, scanned in an omega-theta fashion. At 298K, diffraction points were collected. The modified structure analysis of F2 by full matrix least squares was done with the SHELXL-2014 software package. The lead coordination polymer belongs to a monoclinic system, the space group is P2(1)/n, and the molecular formula is C23H16N2PbO5S, the relative molecular weight is 653.64g/mol, the crystal is monoclinic system, the space group is P2(1)/n, the unit cell parameter is
β＝93.805(3)°；
Z＝4。
Optical property tests show that the polymer has good fluorescence property and quite strong luminous intensity, and has important application value in the fields of color displays, fluorescent marks and the like.
Referring to fig. 1, the basic building block is an asymmetric unit comprising one lead ion, one (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) anion and one coordinated DMF molecule, DMF being N, N-dimethylformamide.
Referring to fig. 2, Pb is observed in the coordination environment of the complex metal as an octadentate coordination pattern, where Pb coordinates with the oxygen atom O5 from seven carboxyl oxygen atoms (O3A, O4A, O1, O2D, O1C, O5, O4B, O1D) on five different (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligands, respectively, in monodentate and chelating coordination, respectively. The Pb-O bond is long at
In the meantime. The carboxyl of (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) is linked to metal Pb by two coordination modes to form a two-dimensional crystal structure.
Referring to fig. 4, comparing the powder diffraction data obtained from the fluorescent coordination polymer sample obtained in fig. 4, the diffraction peak of the obtained fluorescent coordination polymer coincides with the peak simulated by the single crystal diffraction data, which indicates that the purity of the obtained fluorescent coordination polymer powder sample is relatively high, and the experimental reproducibility of the sample is also proved.
Referring to FIG. 5, the thermal stability of the coordination polymer was obtained by thermogravimetric analysis of FIG. 5. The frame of the obtained fluorescent coordination polymer single crystal sample can be stabilized to 400 ℃ through a thermogravimetric analysis curve, and collapse of the framework appears afterwards, so that the prepared material has good thermal stability and is a new material with practical application value.
The solid state fluorescence spectrum of the fluorescent coordination polymer is shown in FIG. 6, and the maximum excitation wavelength is 517 nm. Excitation of the powder sample at 517nm gave a maximum fluorescence emission wavelength at 469 nm. The test of a fluorescence spectrometer at room temperature shows that the polymer has yellow green fluorescence at 517nm and good performance. Optical property tests show that the polymer has good fluorescence property and quite strong luminous intensity, and is expected to have important application value in the fields of color displays, fluorescent marks and the like.
From the CIE chromaticity diagram of fig. 7, it was confirmed that the compound exhibited clear yellow fluorescence and the color was relatively pure.
Claims (9)
1. A lead coordination polymer characterized in that said lead coordination polymer has the formula: [ Pb (L) (DMF) n, n is a positive integer; l is (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) anion, DMF is N, N-dimethylformamide;
the lead coordination polymer is monoclinic system, space group is P2(1)/n, unit cell parameter is
β＝93.805(3)°；
Z＝4。
2. The lead coordination polymer crystal according to claim 1, wherein the Pb — O bond is long at
In the meantime.
3. The lead coordination polymer according to claim 1, wherein the repeating unit of the lead coordination polymer comprises a Pb2+，Pb2+Using an octadentate coordination mode, Pb2+Respectively with seven carboxyl oxygen atoms from five different (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligands and one DMF oxygen atom.
4. The lead coordination polymer according to claim 1, wherein (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) adopts monodentate and chelate coordination modes.
5. The method for producing a lead complex polymer according to any one of claims 1 to 4, comprising the steps of:
1) according to (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid), Pb2+The dosage ratio of the soluble salt to the N, N-dimethylformamide solution is 0.1 mmol: 0.2 mmol: 10mL of (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid), Pb2+And N, N-dimethylformamide solution;
2) dissolving (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) ligand with pH of 4 in N, N-dimethylformamide solution to prepare mixed solution, and adding Pb2+Adding the soluble salt of (a) into the mixed solution;
3) and (3) under a sealed condition, carrying out constant temperature treatment at 120-160 ℃ for 24-72 h, then slowly cooling to room temperature, filtering, and washing to obtain a yellow needle crystal, namely the lead coordination polymer.
6. The method according to claim 5, wherein Pb is2+The soluble salt of (A) is lead nitrate, lead sulfate or lead chloride.
7. The method of claim 5, wherein the washing is with fresh DMF solvent.
8. The process according to claim 5, wherein the pH of the ligand (4, 4' - (2,1, 3-benzothiadiazole-4, 7-diyl) -dibenzoic acid) is adjusted to 4 by adding nitric acid, sulfuric acid or hydrochloric acid dropwise to the ligand.
9. Use of the lead coordination polymer according to any one of claims 1 to 4 as a fluorescent material in the preparation of LED lamps, colored lamps or colored displays.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811253327.4A CN109400899B (en) | 2018-10-25 | 2018-10-25 | Lead coordination polymer and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811253327.4A CN109400899B (en) | 2018-10-25 | 2018-10-25 | Lead coordination polymer and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109400899A CN109400899A (en) | 2019-03-01 |
| CN109400899B true CN109400899B (en) | 2021-03-16 |
Family
ID=65469742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811253327.4A Active CN109400899B (en) | 2018-10-25 | 2018-10-25 | Lead coordination polymer and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109400899B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109894084B (en) * | 2019-03-19 | 2022-02-22 | 集美大学 | Method for preparing lead-based metal organic framework phosphorescent material |
| CN110128670B (en) * | 2019-05-15 | 2021-04-13 | 安徽大学 | Halo-containing SP-MOF crystal, preparation method and perovskite solar cell |
| CN111303204B (en) * | 2020-03-23 | 2022-09-23 | 沈阳师范大学 | Two-dimensional metal organic complex containing thiazole functional group and preparation method and application thereof |
| CN112552521A (en) * | 2020-12-03 | 2021-03-26 | 南京艾姆材料科技有限公司 | Preparation and application method of large-aperture MOF material based on benzothiadiazole |
| CN113121582B (en) * | 2021-03-02 | 2023-05-23 | 长江大学 | Lead coordination polymer, preparation method and application |
| CN113024596B (en) * | 2021-03-23 | 2023-05-30 | 陕西科技大学 | Lead-based inorganic anion complex white light material and preparation method and application thereof |
| CN113024597B (en) * | 2021-03-23 | 2023-06-27 | 陕西科技大学 | Lead-based inorganic anion complex fluorescent color-changing material, and preparation method and application thereof |
| CN114349974B (en) * | 2022-01-27 | 2022-09-20 | 西安电子科技大学 | Novel europium-based MOF material, preparation method thereof and application thereof in detection of ethylamine and gossypol |
| CN114316291B (en) * | 2022-01-27 | 2022-12-30 | 德州学院 | Metal-organic framework based on trispyrazole ligand, preparation method and application of metal-organic framework in organic dye degradation |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106478645A (en) * | 2016-09-21 | 2017-03-08 | 陕西科技大学 | A kind of fragrant cyclosubstituted spiro indole diketopiperazine compound and its synthetic method |
| CN107057081A (en) * | 2017-04-24 | 2017-08-18 | 桂林理工大学 | Preparation, structure and its photoluminescent property of M-phthalic acid lead polymer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002236458A1 (en) * | 2000-11-17 | 2002-05-27 | Pharmacyclics, Inc. | Texaphyrin coordination compounds and uses thereof |
-
2018
- 2018-10-25 CN CN201811253327.4A patent/CN109400899B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106478645A (en) * | 2016-09-21 | 2017-03-08 | 陕西科技大学 | A kind of fragrant cyclosubstituted spiro indole diketopiperazine compound and its synthetic method |
| CN107057081A (en) * | 2017-04-24 | 2017-08-18 | 桂林理工大学 | Preparation, structure and its photoluminescent property of M-phthalic acid lead polymer |
Non-Patent Citations (2)
| Title |
|---|
| A thiadiazole-functionalized Zr(IV)-based metal-organic framework as a highly fluorescent probe for the selective detection of picric acid;Mostakim,S.K等;《CRYSTENGCOMM》;20161231;第18卷(第17期);3104-3113 * |
| Thiadiazole-functional porous metal-organic framework as luminescent probe for Cd2+;Wei, Na等;《CRYSTENGCOMM》;20131231;第15卷(第44期);8883-8886 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109400899A (en) | 2019-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109400899B (en) | Lead coordination polymer and preparation method and application thereof | |
| CN106459095B (en) | Metal Organic Framework (MOF) yellow phosphor and application thereof in white light emitting device | |
| CN107226914B (en) | Terbium organic framework complex and preparation method thereof | |
| CN106750350B (en) | A kind of ternary RE organic frame crystalline material, its synthetic method and application | |
| CN109776813B (en) | Red fluorescent zinc organic supramolecules, and preparation method and application thereof | |
| Wang et al. | Accurate tuning of rare earth metal–organic frameworks with unprecedented topology for white-light emission | |
| CN106046388B (en) | A kind of furancarboxylic acid class rare earth neodymium metal-organic framework luminescent material and its synthetic method | |
| CN109384804B (en) | Copper-iodine complex of hexamethylenetetramine ligand, preparation method and application thereof | |
| CN106589397A (en) | Crystal material, synthesizing method thereof, and application of crystal material as fluorescent crystal material | |
| CN117004039B (en) | Cadmium-based self-adaptive host and guest luminescent coordination polymer and preparation method and application thereof | |
| CN110655655A (en) | Cyan fluorescent zinc-organic coordination polymer and preparation method and application thereof | |
| Chu et al. | A new luminescent lanthanide supramolecular network possessing free Lewis base sites for highly selective and sensitive Cu 2+ sensing | |
| CN112592358B (en) | Blue light luminescent crystal material and preparation method and application thereof | |
| CN110551292A (en) | preparation method of rare earth luminescent material with adjustable light color | |
| CN114874145B (en) | Water-soluble trityl free base material, preparation method and application thereof | |
| CN108586505B (en) | Europium complex red-light material based on two different first ligands and preparation method thereof | |
| CN113072929B (en) | Sandwich type organic supermolecule fluorescent polymer and preparation method and application thereof | |
| CN110698502B (en) | Rare earth complex constructed by benzimidazole derivative and 1, 2-cyclohexanediamine and preparation method and application thereof | |
| Si et al. | Synthesis and photoelectric properties of Ir III complexes using fluorobenzylimidazole [2, 1-b] thiazole derivatives as primary ligands | |
| Liu et al. | Dual emissions and thermochromic luminescences of isomorphic chiral twofold interpenetrated 3-D nets built from I 1 O 2 type hybrid inorganic–organic frameworks of [NH 2 (CH 3) 2] 3 [Pb 2 X 3 (BDC) 2](X= Br, I) | |
| CN113493473A (en) | High-efficiency red-light europium complex luminescent material and preparation method and application thereof | |
| CN114773620B (en) | Double-helix molecule-based green fluorescent polymeric material and preparation and application thereof | |
| CN104447874A (en) | Preparation method and application method of metal complex | |
| CN117285720B (en) | Rare earth luminous coordination polymer and preparation method and application thereof | |
| CN110627819B (en) | Dysprosium complex constructed by benzimidazole derivative and 1, 2-cyclohexanediamine as well as preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |