CN108191915B - Method for preparing rewritable paper based on ionic four-coordinate manganese compound - Google Patents
Method for preparing rewritable paper based on ionic four-coordinate manganese compound Download PDFInfo
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- 150000002697 manganese compounds Chemical class 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 239000000243 solution Substances 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- -1 polyethylene Polymers 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 26
- 239000003446 ligand Substances 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000011572 manganese Substances 0.000 description 24
- 230000000694 effects Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000000295 emission spectrum Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- KCFOLUKWAIAKFB-UHFFFAOYSA-N CCC(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1.Br Chemical compound CCC(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1.Br KCFOLUKWAIAKFB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 231100000086 high toxicity Toxicity 0.000 description 2
- HHDPJRSXPOGIOP-UHFFFAOYSA-L manganese(2+);dibromide;tetrahydrate Chemical compound O.O.O.O.[Mn+2].[Br-].[Br-] HHDPJRSXPOGIOP-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000009270 solid waste treatment Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
-
- 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
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
- D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/80—Paper comprising more than one coating
- D21H19/82—Paper comprising more than one coating superposed
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses a method for preparing rewritable paper based on an ionic four-coordinate manganese compound, which is used for solving the problems of various energy sources and pollution caused by one-time reading and use of printing paper in the prior art and preparing a luminous ionic four-coordinate manganese compound, wherein the compound can be used in the field of pure water duplicating printing paper to provide powerful support for future green printing; the synthesis steps of the organophosphorus ligand involved in the invention are simple, the conditions are mild, and the obtained ionic four-coordination manganese compound has the advantages of low cost, easy obtaining and stable performance.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric functional materials, and particularly relates to a method for preparing rewritable paper based on an ionic four-coordination manganese compound.
Background
In the past centuries, paper has served as the most important medium for human beings to record and transmit information, and most of printing paper can be used only by one-time reading. Paper production and deforestation pose serious social problems.
In recent years, reversible stimulus response materials are widely concerned by people, low-cost, green and environment-friendly repeatable printing paper can be obtained by applying the materials to the printing paper, the problems of garbled and excessive forest trees, difficult solid waste treatment, serious environmental pollution, huge energy consumption and the like are solved, and the birth of the materials undoubtedly can bring outstanding contribution and huge economic benefits to the society. At present, a plurality of groups have researched repeatable printing paper, but the repeatable printing paper also has a plurality of defects, such as high toxicity of the dye, complex material synthesis, high manufacturing cost and the like.
Ionic tetradentate manganese compounds have been favored because of their low cost, ready availability, and stable performance. However, the application in printing is not reported at present. Therefore, the photophysical properties of the manganese complex need to be reasonably regulated, and a novel, rapid and convenient method is researched to realize the change of the luminescent color of the manganese complex under the condition of water jet so as to realize the printing and erasing of information.
Disclosure of Invention
In view of the existing problems, the invention aims to provide an ionic four-coordinate manganese compound, a preparation method thereof and application of the compound in rewritable paper, which can provide powerful support for further development of green printing.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: the invention relates to a luminous ionic four-coordinate manganese compound, which has the following structural general formula:
wherein
X is: br4 2-、Cl4 2-、Br2Cl2 2-、Br2I2 2-、Cl2I2 2-、I4 2-
The structure of R is:
wherein n and m are positive integers between 1 and 5.
The synthesis method and the performance of P-M-X are similar, taking P-Mn as an example, the preparation steps of P-Mn are mainly as follows: 1. synthesis of organophosphorus ligand: bromoethane and triphenylphosphine in a molar ratio of 1:1, uniformly mixing in a toluene solution, heating and refluxing for 24 hours at 120 ℃, adding ether for settling to obtain an ethyl triphenyl phosphine bromide ligand, wherein the structural formula of the organophosphorus ligand is as follows:
2. synthesis of ionic four-coordinate manganese compound: in an acetone solvent system, reacting an organophosphorus ligand P and manganese bromide tetrahydrate for 2 hours at 65 ℃ according to a molar ratio of 1:1, filtering, and spin-drying, wherein the structural formula of P-Mn is as follows:
the ionic four-coordinate manganese compound can be applied to pure water printing carbon paper, and the preparation method of the ionic four-coordinate manganese compound carbon paper is characterized by comprising the following specific operation steps of:
1. coating polyethylene glycol-polypropylene glycol-polyethylene glycol (PEG-PPG-PEG) solution dissolved in dichloromethane on the filter paper, and drying to obtain a first layer;
2. uniformly coating a manganese complex dissolved in dichloromethane and a PEG-PPG-PEG mixed solution on the first layer in the step 1 to form a second layer;
3. the second layer prepared in step 2 was coated with PEG-PPG-PEG as a third layer.
The invention has the beneficial effects that: the invention aims to solve the problems of wood disorder cutting and excessive felling, difficult solid waste treatment, serious environmental pollution, large energy consumption and the like caused by one-time reading and use of printing paper in the prior art, and prepares a luminous ionic four-coordination manganese compound; the synthesis steps of the organophosphorus ligand involved in the invention are simple, the conditions are mild, and the obtained ionic four-coordination manganese compound has the advantages of low cost, easy obtaining and stable performance; the printing image on the pure water rewritable paper prepared by the invention can be kept for a long time, and compared with the prior art, the invention has made a breakthrough progress.
Drawings
FIG. 1 shows a concentration of 1.0 × 10-5Emission spectra of diluted solutions of M in P-Mn in different solvents;
FIG. 2 shows the concentration of 1.0 × 10-5Emission spectra of the mixed solution of M P-Mn n-hexane and water under different water contents;
FIG. 3 is a graph of P-Mn concentration versus cell activity;
FIG. 4 is an emission spectrum of P-Mn at the same concentration under different humidities;
FIG. 5 is a graph showing the effect of the disclosed ionic four-coordinate manganese compound on water printing;
FIG. 6 is a graph of the emission spectra on paper before and after water printing;
fig. 7 is a graph showing a change in the effect of water printing under heating conditions.
Detailed Description
In order to make those skilled in the art better understand the technical solution of the present invention, the following further describes the technical solution of the present invention with reference to the drawings and the embodiments.
With reference to the attached figures 1-6
A luminous ionic four-coordinate manganese compound has the following structural general formula:
wherein
X is: br4 2-、Cl4 2-、Br2Cl2 2-、Br2I2 2-、Cl2I2 2-、I4 2-
The structure of R is:
wherein n and m are positive integers between 1 and 5.
The synthesis method and the performance of P-M-X are similar, taking P-Mn as an example, the preparation steps of P-Mn are mainly as follows: 1. synthesis of organophosphorus ligand: bromoethane and triphenylphosphine in a molar ratio of 1:1, uniformly mixing in a toluene solution, heating and refluxing for 24 hours at 120 ℃, adding ether for settling to obtain an ethyl triphenyl phosphine bromide ligand, wherein the structural formula of the organophosphorus ligand is as follows:
2. synthesis of ionic four-coordinate manganese compound: reacting an organophosphorus ligand P and manganese bromide tetrahydrate at 65 ℃ for 2 hours in an acetone solvent system according to a molar ratio of 1:1, filtering and spin-drying; the structural formula of the ionic four-coordinate manganese compound P-Mn is as follows:
the specific synthetic route is as follows:
the ionic four-coordinate manganese compound can be applied to the aspect of pure water printing carbon paper, and the preparation method of the ionic four-coordinate manganese compound carbon paper comprises the following specific operation steps:
1. coating polyethylene glycol-polypropylene glycol-polyethylene glycol (PEG-PPG-PEG) solution dissolved in dichloromethane on the filter paper, and drying to obtain a first layer;
2. uniformly coating the ionic four-coordinate manganese compound dissolved in dichloromethane and a PEG-PPG-PEG mixed solution on the first layer in the step 1 to form a second layer;
3. the second layer prepared in step 2 was coated with PEG-PPG-PEG as a third layer.
The following studies on the ionic four-coordinate manganese compound of the present invention have been made with respect to the application prospects
1. Characterization of compound P and application of P — Mn:
(1) dissolving the compound P (5-10mg) in a deuterated reagent with the concentration of 0.5m L, and respectively representing the structures of the compounds by using a 400Hz nuclear magnetic instrument;
characterization of organophosphorus ligand P:
1H NMR(400MHz，CDCl3)
7.62-7.89(m，15H)，3.83(m，2H)，8.21-8.07(m，2H)，3.83(dq，2H)，1.37(m，2H)。
13C NMR(400MHz，CDCl3)
134.6，133.04，130.02，117.34，16.55，6.29。
(2) the preparation concentration is 1.0 × 10-5M in diluted P-Mn solution, measured in different solvents such as ethanol (Ethnol), Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), water (H)2O), n-hexane, P-n-hexane, Tetrahydrofuran (THF) and dichloromethane (CH)2Cl2) The specific experimental results are shown in fig. 1:
as is clear from FIG. 1, except that P-Mn in the n-hexane solution emitted green light (excitation wavelength: 254nm, emission peak: 522nm), the remaining solution was in a fluorescence quenching state.
(3) The preparation concentration is 1.0 × 10-5The emission spectrum of the mixed solution of M, P-Mn n-hexane and water under different water contents is measured, and the experimental result is shown in figure 2:
as can be seen from fig. 2, the emission intensity gradually increases as the water content decreases. The water is illustrated to have the effect of quenching fluorescence, and the result shows that the ionic four-coordinate manganese compound based on the invention is expected to realize water printing.
(3) Evaluation of cytotoxicity studies of P-Mn using Hela cells, the results are shown in FIG. 3:
as can be seen from FIG. 3, the cell activity of P-Mn is maintained at 80%, which indicates that the toxicity of P-Mn is low, and the compound of the present invention has better application prospect in water printing compared with the dye with high toxicity in the prior art.
Humidity test of P-Mn and research of photophysical properties of copy paper for water printing
(1) P-Mn dichloro solution with concentration of 5mg/m L was prepared and spin-coated on a quartz plate, and its emission spectra at different humidities were measured, and the results are shown in FIG. 4:
as can be seen from FIG. 4, the emission peak at 522nm gradually decreased with increasing humidity, indicating that the fluorescence of P-Mn was quenched by water, which provides the possibility for the next water printing.
(2) Research on water printing effect: as shown in fig. 5, the water-printed information does not change significantly in definition after one year, and the printed image can be retained on the paper for a long time, which has made a breakthrough progress compared to the pure water rewritable paper in the prior art.
(3) The change of the emission spectrum and the display effect on the paper before and after water printing are shown in fig. 6-7: from the figure, it can be found that the change of the emission intensity of the carbon paper before and after water printing is basically consistent with that of figure 4, and the fluorescence of P-Mn is quenched by the water, so that an ideal effect is achieved, and the aim of pure water printing is fulfilled.
Claims (1)
1. The method for preparing the rewritable paper based on the ionic four-coordinate manganese compound is characterized by comprising the following specific operation steps of:
(1) coating polyethylene glycol-polypropylene glycol-polyethylene glycol (PEG-PPG-PEG) solution dissolved in dichloromethane on the filter paper, and drying to obtain a first layer;
(2) uniformly coating the ionic four-coordinate manganese compound dissolved in dichloromethane and a PEG-PPG-PEG mixed solution on the first layer in the step 1 to form a second layer;
(3) coating PEG-PPG-PEG on the second layer prepared in the step 2 as a third layer;
the ionic four-coordinate manganese compound has a structural general formula as follows:
wherein, X is: br4 2-、Cl4 2-、Br2Cl2 2-、Br2I2 2-、Cl2I2 2-、I4 2-。
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| US11034709B2 (en) * | 2019-05-29 | 2021-06-15 | The Hong Kong University Of Science And Technology | Organic long persistence luminescence compositions |
| CN110256497A (en) * | 2019-06-06 | 2019-09-20 | 宁波大学 | A kind of manganese complex luminescent material and its preparation method and application |
| CN112341491A (en) * | 2020-11-09 | 2021-02-09 | 中国计量大学 | Organic-inorganic hybrid long afterglow material, preparation method thereof and application thereof in ink-jet printing |
| CN114057796B (en) * | 2021-11-12 | 2023-05-16 | 郑州大学 | Hybrid material based on organic-metal manganese halide and preparation method thereof |
| CN114634528A (en) * | 2022-02-11 | 2022-06-17 | 华南理工大学 | Efficient narrow-band green light emitting metal halide and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3014621B1 (en) * | 1980-04-16 | 1981-04-23 | MD Papierfabriken Heinrich Nicolaus GmbH, 8060 Dachau | Response carbon paper |
| US5508180A (en) * | 1993-04-19 | 1996-04-16 | Enzymol International, Inc. | Biocatalytic oxidation using soybean peroxidase |
| JP4325314B2 (en) * | 2003-08-12 | 2009-09-02 | 東洋インキ製造株式会社 | Resin production method and ink |
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2018
- 2018-01-24 CN CN201810069029.3A patent/CN108191915B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3014621B1 (en) * | 1980-04-16 | 1981-04-23 | MD Papierfabriken Heinrich Nicolaus GmbH, 8060 Dachau | Response carbon paper |
| US5508180A (en) * | 1993-04-19 | 1996-04-16 | Enzymol International, Inc. | Biocatalytic oxidation using soybean peroxidase |
| JP4325314B2 (en) * | 2003-08-12 | 2009-09-02 | 東洋インキ製造株式会社 | Resin production method and ink |
Non-Patent Citations (2)
| Title |
|---|
| Correlation of Structure and Triboluminescence for Tetrahedral Manganese(II) Compounds;F. Albert Cotton等，;《Inorg. Chem.》;20010605;第40卷;第3576-3578页 * |
| Triboluminescence and Vapor-Induced Phase Transitions in the Solids of Methyltriphenylphosphonium Tetrahalomanganate(II) Complexes;Sujitha Balsamy等，;《Inorg. Chem.》;20140605;第53卷;参见第6055页方案1、第6058页左栏最后一段 * |
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