CN115724861B - High-sensitivity detection MnO 4- Preparation method and product of anthracene alkynyl-containing luminescent crystal material - Google Patents

High-sensitivity detection MnO 4- Preparation method and product of anthracene alkynyl-containing luminescent crystal material Download PDF

Info

Publication number
CN115724861B
CN115724861B CN202211345423.8A CN202211345423A CN115724861B CN 115724861 B CN115724861 B CN 115724861B CN 202211345423 A CN202211345423 A CN 202211345423A CN 115724861 B CN115724861 B CN 115724861B
Authority
CN
China
Prior art keywords
anthracene
aep
tdc
mno
mixed solution
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
Application number
CN202211345423.8A
Other languages
Chinese (zh)
Other versions
CN115724861A (en
Inventor
张金方
林卓
李文静
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beijing Zhichanhui Technology Co ltd
Original Assignee
Jiangnan University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jiangnan University filed Critical Jiangnan University
Priority to CN202211345423.8A priority Critical patent/CN115724861B/en
Publication of CN115724861A publication Critical patent/CN115724861A/en
Application granted granted Critical
Publication of CN115724861B publication Critical patent/CN115724861B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Luminescent Compositions (AREA)

Abstract

The application provides a method for detecting MnO with high sensitivity 4 Anthracene alkynyl-containing luminescent crystal material [ Zn (AEP) 2 (2,5‑TDC)] n Zinc nitrate, 4- [2- (anthracene-9-yl) ethynyl)]Adding pyridine and 2, 5-thiophene dicarboxylic acid into a mixed solution of water and methanol, stirring to obtain a mixed solution, heating the mixed solution in a closed reaction kettle for reaction, slowly cooling to room temperature, and filtering, washing and drying a product to obtain the luminescent crystal material. The application is based on 4- [2- (anthracene-9-yl) ethynyl for the first time]Pyridine gives a luminescent crystalline material [ Zn (AEP) 2 (2,5‑TDC)] n, And the luminescent quenching high-sensitivity detection of the aqueous phase MnO 4 The synthetic route is simple and easy to control, is suitable for industrialized production, and prepares the obtained material [ Zn (AEP) 2 (2,5‑TDC)] n The highest yield can reach 56%. Quenching constant K sv =1.0×10 4 M ‑1 The detection limit is 1.4X10 ‑3 mM。

Description

High-sensitivity detection MnO 4- Preparation method and product of anthracene alkynyl-containing luminescent crystal material
Technical Field
The application belongs to the technical field of luminescent detection functional materials, and in particular relates to a luminescent quenching aqueous phase detection MnO 4 - The preparation method and the product of the luminescent crystal material containing anthracene alkynyl.
Background
Environmental pollution has become a global concern, and water pollution is now a concernStill very severe. MnO (MnO) 4 - (permanganate) is a serious water resource contaminant, often used as an important oxidant, as a preservative and disinfectant, widely used in fishery and aquaculture. Excess MnO 4 - Can cause allergic reaction, genetic defect, various cancer diseases, etc. Thus developing high-efficiency aqueous phase detection of MnO 4 - The functional material of (2) appears to be extremely important.
Metal-organic framework crystalline materials have been developed for use in the field of luminescence detection. The functional organic ligand plays a decisive role in the luminescence detection performance of the metal-organic framework crystal material. Therefore, the development of novel functional organic ligand synthesis of metal-organic framework crystal materials with luminescence detection function has important significance.
Disclosure of Invention
This section is intended to outline some aspects of embodiments of the application and to briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section as well as in the description of the application and in the title of the application, which may not be used to limit the scope of the application.
The present application has been made in view of the above-mentioned and conventional problems occurring in the prior art.
Accordingly, an object of the present application is to provide a highly sensitive detection method for MnO 4 - The preparation method and the product of the luminescent crystal material containing anthracene alkynyl.
In order to solve the technical problems, according to one aspect of the present application, the following technical solutions are provided: high-sensitivity detection MnO 4 - The preparation method of the anthracene-containing alkynyl luminescent crystal material comprises the steps of,
zinc nitrate, 4- [2- (anthracene-9-yl) ethynyl]Pyridine (AEP) and 2, 5-thiophenedicarboxylic acid (2, 5-H) 2 TDC) is added into the mixed solvent and stirred to prepare mixed solution;
heating the mixed solution in a closed reaction kettle for reaction, slowly cooling to room temperature, filtering, washing and drying the product to obtain an anthracene-alkynyl-containing luminescent crystal material [ Zn (AEP) ] 2 (2,5-TDC)] n
As a highly sensitive detection of MnO according to the present application 4 - A preferred scheme of the preparation method of the luminescent crystal material containing anthracene alkyne is as follows: the zinc nitrate and 4- [2- (anthracene-9-yl) ethynyl]The molar ratio of pyridine to 2, 5-thiophenedicarboxylic acid is 1:0.5 to 1.5:0.5 to 1.
As a highly sensitive detection of MnO according to the present application 4 - A preferred scheme of the preparation method of the luminescent crystal material containing anthracene alkyne is as follows: the volume ratio of the water to the methanol is 1:0.5 to 1.5 percent of mixed solution.
As a highly sensitive detection of MnO according to the present application 4 - A preferred scheme of the preparation method of the luminescent crystal material containing anthracene alkyne is as follows: the volume of the mixed solvent required for adding 0.1mmol of zinc nitrate is 4-8 mL.
As a highly sensitive detection of MnO according to the present application 4 - A preferred scheme of the preparation method of the luminescent crystal material containing anthracene alkyne is as follows: the heating reaction is carried out at the temperature of 100-120 ℃ for 36-72 h.
As a highly sensitive detection of MnO according to the present application 4 - A preferred scheme of the preparation method of the luminescent crystal material containing anthracene alkyne is as follows: the cooling rate for cooling to room temperature is 2-5 ℃/h.
As a highly sensitive detection of MnO according to the present application 4 - A preferred scheme of the preparation method of the luminescent crystal material containing anthracene alkyne is as follows: the washing solvent is water and methanol with the volume ratio of 1:0.5 to 1.5 percent of mixed liquor.
As a highly sensitive detection of MnO according to the present application 4 - A preferred scheme of the preparation method of the luminescent crystal material containing anthracene alkyne is as follows: the drying is vacuum drying, the drying temperature is 50-80 ℃, and the drying time is 10-30 min.
As a highly sensitive detection of MnO according to the present application 4 - Material [ Zn (AEP)) 2 (2,5-TDC)] n Wherein n is an unlimited range.
As a highly sensitive detection of MnO according to the present application 4 - A preferred scheme of the preparation method of the luminescent crystal material containing anthracene alkyne is as follows: said material [ Zn (AEP) 2 (2,5-TDC)] n Detection of aqueous MnO by luminescence quenching 4 - Has a quenching constant of 1.0X10 4 M -1 The detection limit is 1.4X10 -3 mM。
The application has the beneficial effects that:
(1) The application provides a method for detecting MnO with high sensitivity 4 - Anthracene alkynyl-containing luminescent crystal material [ Zn (AEP) 2 (2,5-TDC)] n Zinc nitrate, 4- [2- (anthracene-9-yl) ethynyl)]Adding pyridine and 2, 5-thiophene dicarboxylic acid into a mixed solution of water and methanol, stirring to obtain a mixed solution, heating the mixed solution in a closed reaction kettle for reaction, slowly cooling to room temperature, and filtering, washing and drying a product to obtain the luminescent crystal material.
(2) The application is based on 4- [2- (anthracene-9-yl) ethynyl for the first time]Pyridine gives a luminescent crystalline material [ Zn (AEP) 2 (2,5-TDC)] n, And the luminescent quenching high-sensitivity detection of the aqueous phase MnO 4 - The synthetic route is simple and easy to control, is suitable for industrialized production, and prepares the obtained material [ Zn (AEP) 2 (2,5-TDC)] n The yield can reach 56% (calculated by AEP). Quenching constant K sv =1.0×10 4 M -1 The detection limit is 1.4X10 -3 mM。
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present application, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art. Wherein:
FIG. 1 shows the crystalline material [ Zn (AEP) of examples 1-8 ] 2 (2,5-TDC)] n A two-dimensional crystal structure diagram (hydrogen atom omitted);
FIG. 2 shows the crystalline material [ Zn (AEP) of examples 1-8 ] 2 (2,5-TDC)] n Powder X-ray diffraction patterns of (2);
FIG. 3 shows the crystalline material [ Cd (NDA) (3-L) (H) prepared in examples 1-8 2 O)] n Excitation and emission spectra (maximum excitation wavelength 404nm; maximum emission wavelength 588 nm) of the aqueous suspension (0.2 mg/mL);
FIG. 4 is 2.5mL of crystalline material [ Zn (AEP) 2 (2,5-TDC)] n To the aqueous suspension (0.1 mg/mL) of different volumes of MnO 4 - A graph of change in luminous intensity of an aqueous solution (2 mmol/L);
FIG. 5 shows the crystalline material [ Zn (AEP) of examples 1-8 ] 2 (2,5-TDC)] n Detection of MnO 4 - Quenching constant curve of (2);
FIG. 6 shows the crystalline material [ Zn (AEP) of examples 1-8 ] 2 (2,5-TDC)] n Detection of MnO 4 - Is a detection limit curve of (2).
Detailed Description
In order that the above-recited objects, features and advantages of the present application will become more apparent, a more particular description of the application will be rendered by reference to specific embodiments thereof.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present application, but the present application may be practiced in other ways other than those described herein, and persons skilled in the art will readily appreciate that the present application is not limited to the specific embodiments disclosed below.
Further, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic can be included in at least one implementation of the application. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
The chemical reagents used in the examples of the present application, unless otherwise specified, were all of the usual commercial analytical grade.
The method for calculating the yield in the embodiment of the application comprises the following steps: the yield was calculated based on AEP, the calculation steps were:
the 4- [2- (anthracene-9-yl) ethynyl ] pyridine used in the examples was prepared in the laboratory as follows:
carbon tetrabromide and triphenylphosphine are added into methylene dichloride to react for 20 minutes at room temperature, anthracene-9-formaldehyde is added, and the mixture is heated and stirred for 48 hours under the protection of nitrogen. The reaction mixture was cooled to room temperature, washed with toluene and the filtrate evaporated to give the crude product. Stirring the crude product with ethanol to obtain a pale yellow product 9- (2, 2-dibromovinyl) anthracene;
adding 9- (2, 2-dibromovinyl) anthracene, anhydrous sodium carbonate, triphenylphosphine, 4-pyridine boric acid and palladium acetate catalyst into a mixed solvent of 1, 4-dioxane/H 2 O (V/v=4/1). The reaction mixture was heated to 120 ℃ under nitrogen for 20 hours at reflux. After cooling to room temperature, distilled water was added to the mixture, and extraction was performed with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered and the solvent was evaporated to dryness to give the crude product. The crude product was obtained by column chromatography using ethyl acetate/petroleum ether (V: v=3/7) as eluent, and washed with ethyl acetate to give 4- [2- (anthracen-9-yl) ethynyl as a pale yellow product]Pyridine.
Example 1:
0.1mmol of zinc nitrate, 0.05 mmole of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.05 mmole of 2, 5-thiophene dicarboxylic acid were added to 6mL of water and methanol (V: V=1:1) and stirred to prepare a mixed solution;
the prepared mixed solution is placed in a closed reaction kettle, heated to 110 ℃ for reaction for 48 hours, cooled slowly to room temperature at the speed of 2 ℃/h, and then filtered, washed by mixed solution of water and methanol (V: V=1:1), and dried in vacuum at 80 ℃ for 15 minutes to obtain the crystalline material [ Zn (AEP) 2 (2,5-TDC)] n . The calculated yields were: 56%.
Example 2:
0.1mmol of zinc nitrate, 0.1mmol of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.05 mmole of 2, 5-thiophene dicarboxylic acid were added to 6mL of water and methanol (V: v=1:1) and stirred to prepare a mixed solution;
the prepared mixed solution is placed in a closed reaction kettle, heated to 110 ℃ for reaction for 48 hours, cooled slowly to room temperature at the speed of 2 ℃/h, and then filtered, washed by mixed solution of water and methanol (V: V=1:1), and dried in vacuum at 80 ℃ for 15 minutes to obtain the crystalline material [ Zn (AEP) 2 (2,5-TDC)] n . The calculated yields were: 50%.
Example 3:
0.1mmol of zinc nitrate, 0.05 mmole of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.01 mmole of 2, 5-thiophene dicarboxylic acid were added to 6mL of water and methanol (V: V=1:1) and stirred to prepare a mixed solution;
the prepared mixed solution is placed in a closed reaction kettle, heated to 110 ℃ for reaction for 48 hours, cooled slowly to room temperature at the speed of 2 ℃/h, and then filtered, washed by mixed solution of water and methanol (V: V=1:1), and dried in vacuum at 80 ℃ for 15 minutes to obtain the crystalline material [ Zn (AEP) 2 (2,5-TDC)] n . The calculated yields were: 52%.
Example 4:
0.1mmol of zinc nitrate, 0.05 mmole of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.05 mmole of 2, 5-thiophene dicarboxylic acid were added to 8mL of water and methanol (V: V=1:1) and stirred to prepare a mixed solution;
the prepared mixed solution is placed in a closed reaction kettle, heated to 110 ℃ for reaction for 48 hours, cooled slowly to room temperature at the speed of 2 ℃/h, and then filtered, washed by mixed solution of water and methanol (V: V=1:1), and dried in vacuum at 80 ℃ for 15 minutes to obtain the crystalline material [ Zn (AEP) 2 (2,5-TDC)] n . The calculated yields were: 55%.
Example 5:
0.1mmol of zinc nitrate, 0.05 mmole of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.05 mmole of 2, 5-thiophene dicarboxylic acid were added to 6mL of water and methanol (V: V=1:1.5) and stirred to prepare a mixed solution;
the prepared mixed solution is placed in a closed reaction kettle, heated to 110 ℃ for reaction for 48 hours, and slowly cooled to a room at the speed of 2 ℃/hFiltering the product after the temperature, washing with a mixed solution of water and methanol (V: V=1:1), and vacuum drying at 80 ℃ for 10min to obtain a crystalline material [ Zn (AEP) 2 (2,5-TDC)] n . The calculated yields were: 52%.
Example 6:
0.1mmol of zinc nitrate, 0.05 mmole of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.05 mmole of 2, 5-thiophene dicarboxylic acid were added to 6mL of water and methanol (V: V=1:1) and stirred to prepare a mixed solution;
heating the prepared mixed solution to 120 ℃ in a closed reaction kettle for reaction for 48 hours, slowly cooling to room temperature at a speed of 2 ℃/h, filtering a product, washing with a mixed solution of water and methanol (V: V=1:1), and vacuum-drying at 80 ℃ for 15 minutes to obtain a crystalline material [ Zn (AEP) 2 (2,5-TDC)] n . The calculated yields were: 55%.
Example 7:
0.1mmol of zinc nitrate, 0.05 mmole of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.05 mmole of 2, 5-thiophene dicarboxylic acid were added to 6mL of water and methanol (V: V=1:1) and stirred to prepare a mixed solution;
heating the prepared mixed solution to 110 ℃ in a closed reaction kettle for reaction for 60 hours, slowly cooling to room temperature at a speed of 2 ℃/h, filtering the product, washing with a mixed solution of water and methanol (V: V=1:1), and vacuum-drying at 80 ℃ for 15 minutes to obtain a crystalline material [ Zn (AEP) 2 (2,5-TDC)] n . The calculated yields were: 56%.
Example 8:
0.1mmol of zinc nitrate, 0.05 mmole of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.05 mmole of 2, 5-thiophene dicarboxylic acid were added to 6mL of water and methanol (V: V=1:1) and stirred to prepare a mixed solution;
the prepared mixed solution is placed in a closed reaction kettle, heated to 110 ℃ for reaction for 48 hours, cooled slowly to room temperature at the speed of 5 ℃/h, filtered, washed by mixed solution of water and methanol (V: V=1:1), and dried in vacuum at 80 ℃ for 15 minutes, thus obtaining the crystalline material [ Zn (AEP) ] 2 (2,5-TDC)] n . The calculated yields were: 55%.
Example 9:
0.1mmol of zinc nitrate, 0.05 mmole of 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 0.05 mmole of 2, 5-thiophene dicarboxylic acid were added to 6mL of water and methanol (V: V=1:1) and stirred to prepare a mixed solution;
the prepared mixed solution is placed in a closed reaction kettle, heated to 110 ℃ for reaction for 48 hours, cooled slowly to room temperature at the speed of 2 ℃/h, and then the product is filtered, washed by mixed solution of water and methanol (V: V=1:1.5), and dried in vacuum at 80 ℃ for 15 minutes, thus obtaining the crystalline material [ Zn (AEP) ] 2 (2,5-TDC)] n . The calculated yields were: 55%.
MnO 4 - The detection performance is as follows: 3mg of the prepared crystalline material [ Zn (AEP) 2 (2,5-TDC)] n Dispersing into 30mL of water to obtain stable suspension, adding MnO containing materials with different volumes into the suspension 4 - (2 mmol/L) and its luminescence intensity was measured under excitation light of 404nm, respectively.
Crystalline material [ Zn (AEP) prepared by the application 2 (2,5-TDC)] n The powder X-ray diffraction pattern of the crystal material is basically consistent with the theoretical calculated X-ray diffraction pattern, which shows that the crystal material prepared by the application has high purity.
FIG. 4 is 2.5mL of crystalline material [ Zn (AEP) 2 (2,5-TDC)] n To the aqueous suspension (0.2 mg/mL) of different volumes of MnO 4 - Graph of change in luminous intensity of aqueous solution (2 mmol/L). The luminescence intensity of the aqueous suspension of the crystalline material was measured at an excitation wavelength of 404nm, and then 2mmol/L MnO was gradually added dropwise thereto 4 - Aqueous solution with MnO 4 - The amount gradually increases, and the luminous intensity of the suspension is gradually quenched.
The application provides a method for detecting MnO with high sensitivity 4 - Anthracene alkynyl-containing luminescent crystal material [ Zn (AEP) 2 (2,5-TDC)] n Zinc nitrate, 4- [2- (anthracene-9-yl) ethynyl)]Adding pyridine and 2, 5-thiophene dicarboxylic acid into a mixed solution of water and methanol, stirring to obtain a mixed solution, heating the mixed solution in a closed reaction kettle for reaction, slowly cooling to room temperature, and filtering, washing and drying a product to obtain the luminescent crystal material. The application is based on 4- [2- (anthracene-9-yl) ethynyl for the first time]Pyridine obtainingLuminescent crystal material [ Zn (AEP) 2 (2,5-TDC)] n, And the luminescent quenching high-sensitivity detection of the aqueous phase MnO 4 - The synthetic route is simple and easy to control, is suitable for industrialized production, and prepares the obtained material [ Zn (AEP) 2 (2,5-TDC)] n The highest yield can reach 56%. Quenching constant K sv =1.0×10 4 M -1 The detection limit is 1.4X10 -3 mM。
It should be noted that the above embodiments are only for illustrating the technical solution of the present application and not for limiting the same, and although the present application has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present application may be modified or substituted without departing from the spirit and scope of the technical solution of the present application, which is intended to be covered in the scope of the claims of the present application.

Claims (10)

1. Detection MnO 4 - The preparation method of the luminescent crystal material containing anthracene alkyne comprises the following steps: comprising the steps of (a) a step of,
zinc nitrate, 4- [2- (anthracene-9-yl) ethynyl]Pyridine AEP and 2, 5-thiophene dicarboxylic acid 2,5-H 2 Adding TDC into the mixed solvent and stirring to obtain mixed solution;
heating the mixed solution in a closed reaction kettle for reaction, slowly cooling to room temperature, filtering, washing and drying the product to obtain an anthracene-alkynyl-containing luminescent crystal material [ Zn (AEP) ] 2 (2,5-TDC)] n
2. The method of manufacturing according to claim 1, wherein: the molar ratio of zinc nitrate, 4- [2- (anthracene-9-yl) ethynyl ] pyridine and 2, 5-thiophene dicarboxylic acid is 1:0.5 to 1.5:0.5 to 1.
3. The method of manufacturing according to claim 1, wherein: the volume ratio of the water to the methanol is 1:0.5 to 1.5.
4. The method of manufacturing according to claim 1, wherein: the volume of the mixed solvent required for adding 0.1mmol of zinc nitrate is 4-8 mL.
5. The method of manufacturing according to claim 1, wherein: and the heating reaction is carried out, the heating temperature is 100-120 ℃, and the heating time is 36-72 h.
6. The method of manufacturing according to claim 1, wherein: and the cooling rate for cooling to the room temperature is 2-5 ℃/h.
7. The method of manufacturing according to claim 1, wherein: the washing solvent is water and methanol with the volume ratio of 1:0.5 to 1.5.
8. The method of manufacturing according to claim 1, wherein: the drying is vacuum drying, the drying temperature is 50-80 ℃, and the drying time is 10-30 min.
9. The product produced by the production method of any one of claims 1 to 8, characterized in that: the product is [ Zn (AEP) 2 (2,5-TDC)] n Crystalline material.
10. The product of claim 9, wherein: said product [ Zn (AEP) 2 (2,5-TDC)] n Detection of aqueous MnO by luminescence quenching 4 - Has a quenching constant of 1.0X10 4 M -1 The detection limit is 1.4X10 -3 mM。
CN202211345423.8A 2022-10-31 2022-10-31 High-sensitivity detection MnO 4- Preparation method and product of anthracene alkynyl-containing luminescent crystal material Active CN115724861B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211345423.8A CN115724861B (en) 2022-10-31 2022-10-31 High-sensitivity detection MnO 4- Preparation method and product of anthracene alkynyl-containing luminescent crystal material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211345423.8A CN115724861B (en) 2022-10-31 2022-10-31 High-sensitivity detection MnO 4- Preparation method and product of anthracene alkynyl-containing luminescent crystal material

Publications (2)

Publication Number Publication Date
CN115724861A CN115724861A (en) 2023-03-03
CN115724861B true CN115724861B (en) 2023-10-13

Family

ID=85295274

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211345423.8A Active CN115724861B (en) 2022-10-31 2022-10-31 High-sensitivity detection MnO 4- Preparation method and product of anthracene alkynyl-containing luminescent crystal material

Country Status (1)

Country Link
CN (1) CN115724861B (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104402914A (en) * 2014-10-16 2015-03-11 东北师范大学 Zinc metal organic framework material for catalysis degradation of organic dye under visible light

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104402914A (en) * 2014-10-16 2015-03-11 东北师范大学 Zinc metal organic framework material for catalysis degradation of organic dye under visible light

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Li, Jing et al.A Zn(II)/anthracene coordination polymer showing highly efficient photocatalytic Cr(VI) reduction in aqueous solution.Inorganic Chemistry Communications.2019,第101卷52-56. *
Liu, Yue et al.Visible-light-induced controlled radical polymerization of methacrylates mediated by a pillared-layer metal-organic framework.Green Chemistry.2016,第18卷1475-1481. *
Ma, Jian-Xin et al.Three Zn(II) coordination polymers as dual-responsive luminescent probes for highly selective detection of Fe3+ cation and MnO4- anion.Zeitschrift fuer Anorganische und Allgemeine Chemie.2022,第648卷e202100331. *
Zhao, Hongmei et al.Construction of Pillared-Layer MOF as Efficient Visible-Light Photocatalysts for Aqueous Cr(VI) Reduction and Dye Degradation.ACS Sustainable Chemistry & Engineering.2017,第5卷4449-4456. *

Also Published As

Publication number Publication date
CN115724861A (en) 2023-03-03

Similar Documents

Publication Publication Date Title
CN103755702B (en) Phenanthro-imidazo isoquinoline 99.9 and derivative and preparation method thereof thereof and application
Lin et al. A new photochromic-ligand-based luminescent coordination polymer as a MnO 4− sensor with extremely high sensitivity and excellent selectivity
CN113004313A (en) Double-thiophene-double-coumarin-based BODIPY near-infrared fluorescent dye and preparation method thereof
CN115724861B (en) High-sensitivity detection MnO 4- Preparation method and product of anthracene alkynyl-containing luminescent crystal material
CN108456188A (en) A kind of 7- lignocaines -4- methytal coumarins derivative, preparation method and the application as nanometer fragrance precursor
CN113214144B (en) Metal organic framework material based on dipole organic ligand, synthetic method and application thereof
Balch et al. Three-center oxidative addition. Formation, structure, and dissociation of (PhCH2NC) 12Rh3I23+ and related cations
CN113845534B (en) Preparation method and application of high-manganese acid radical luminescent crystal material for extremely sensitive aqueous phase detection
CN109293646B (en) Organic photochromic material and preparation method and application thereof
CN116144036B (en) Luminescent crystal material capable of detecting aqueous phase ornidazole with high sensitivity and preparation method thereof
Grosshenny et al. Synthesis, characterization and properties of novel covalently linked binuclear ruthenium (II) and trinuclear ruthenium (II)–copper (I) bipyridyl complexes
CN116444814B (en) Zinc coordination polymer based on photochromic function organic ligand and preparation method and application thereof
CN109824707B (en) Lanthanide rare earth metal complex of stilbene derivative and preparation method and application thereof
CN114671898B (en) Luminescence-enhanced aqueous phase detection Bi 3+ Preparation method of luminescent crystal material
CN115650962B (en) Fluorescent ligand compound for palladium catalytic coupling reaction and preparation method thereof
CN117603462A (en) Extremely sensitive detection of aqueous phase Fe 3+ Luminescent crystal material of (2) and preparation method thereof
CN118955917A (en) Crystal material based on fluorene ring ligand, preparation method thereof and detection of Hg in luminescence enhancement2+Application in (a)
CN105384744B (en) Four (trifluoro ethoxy) phthalocyanine europium complexes and its preparation method and application
CN115504938B (en) Compound with photoinduced solid fluorescence change and preparation method thereof
JP3653587B2 (en) Photoresponsive material and isomerization method
CN116410084A (en) Fluorene ring-based organic material and preparation method and application thereof
CN116082288B (en) Method for preparing [60] fullerene tricyclic dihydronaphthalene derivative by palladium-catalyzed domino cyclization reaction
CN116082186B (en) Preparation method and application of novel fluorescent probe molecule based on perylene
CN117945988A (en) Organic ion salt with electrochemiluminescence effect and preparation method and application thereof
CN112759616B (en) Tri-discoene carbene palladium compound 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
TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20240514

Address after: 810, 8th Floor, Building 10, Courtyard 1, Tianxing Street, Fangshan District, Beijing, 102400

Patentee after: Beijing Zhichanhui Technology Co.,Ltd.

Country or region after: China

Address before: No. 1800 road 214122 Jiangsu Lihu Binhu District City of Wuxi Province

Patentee before: Jiangnan University

Country or region before: China