CN111171074B - Benzyl triphenyl phosphine tetranuclear manganese (II) complex - Google Patents
Benzyl triphenyl phosphine tetranuclear manganese (II) complex Download PDFInfo
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- CN111171074B CN111171074B CN202010110048.3A CN202010110048A CN111171074B CN 111171074 B CN111171074 B CN 111171074B CN 202010110048 A CN202010110048 A CN 202010110048A CN 111171074 B CN111171074 B CN 111171074B
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- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 title abstract description 7
- OSHRCGBFBSFXGO-UHFFFAOYSA-N (2-benzylphenyl)-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CC1=CC=CC=C1 OSHRCGBFBSFXGO-UHFFFAOYSA-N 0.000 title description 2
- 239000000463 material Substances 0.000 claims abstract description 21
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000013078 crystal Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 7
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- BNQRPLGZFADFGA-UHFFFAOYSA-N benzyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 BNQRPLGZFADFGA-UHFFFAOYSA-N 0.000 abstract description 5
- 229910001510 metal chloride Inorganic materials 0.000 abstract description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 abstract description 2
- 229940116357 potassium thiocyanate Drugs 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000003860 storage Methods 0.000 abstract description 2
- 239000011572 manganese Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 6
- 238000012986 modification Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 230000005284 excitation Effects 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 235000019796 monopotassium phosphate Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000005389 magnetism Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005303 weighing Methods 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
- 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
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- 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
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/57—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing manganese or rhenium
- C09K11/572—Chalcogenides
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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Abstract
The invention discloses a benzyltriphenylphosphonium tetranuclear manganese (II) complex, which has the molecular formula as follows:
the invention synthesizes the hybrid material at room temperature by taking metal chloride, benzyltriphenylphosphonium chloride and potassium thiocyanate as raw materials, and the material has excellent fluorescence property and important value in nonlinear optical property and information storage aspect.
Description
Technical Field
The invention relates to the field of materials, in particular to a benzyltriphenylphosphonium tetranuclear manganese (II) complex, application thereof as a fluorescent material and a preparation method thereof.
Background
The preparation of molecular materials with special structure, optics, conductivity and magnetism using crystal engineering and supramolecular chemistry has attracted considerable interest, with some non-covalent interactions such as weak P.junction interaction or Pi.junction interaction and H-bond interaction being used to obtain some new materials, with wide applications in the field of photovoltaics.
The development trend and direction of the current inorganic chemistry have the characteristics of scientifically combining with materials, compounding, assembling and hybridizing inorganic functional materials by applying molecular design and molecular engineering ideas, strengthening the relationship between the structure and the performance of functional substances and the like. Since these materials are composed of inorganic phase, the structural modification and modification are difficult, and it is difficult to control the size, shape and physicochemical properties according to actual needs. While organic compounds have excellent molecular tailoring and modification functions, they have significant drawbacks in terms of robustness and stability. How to combine the complementary properties of inorganic and organic compounds, and constructing a novel hybrid material with a plastic, stable and firm structure has become an important research topic in the fields of inorganic chemistry and material science. In recent years, the research on the synthesis of Mn (II) -based coordination compounds has attracted considerable attention due to their interesting molecular topology and their great potential for applications in catalysis, magnetism and fluorescence properties.
Disclosure of Invention
The invention aims to provide a novel nonlinear optical material and a synthetic method thereof. In order to realize the purpose of the invention, the following technical scheme is adopted:
one of the objects of the present invention is to provide benzyltriphenylphosphonium tetranuclear manganese (ii) complexes of the formula:
the heterocyclic organic ligand in the molecular structural formula is benzyltriphenylphosphonium chloride, SCN is thiocyanate, and Mn is metal manganese ions.
In a preferred embodiment of the present invention, the complex is a particulate crystal; preferably, the granular crystals are pink granular crystals.
The invention also relates to the application of the benzyltriphenylphosphonium tetranuclear manganese (II) complex as a fluorescent material and/or a nonlinear optical material.
The invention also relates to a preparation method of the benzyltriphenylphosphonium tetranuclear manganese (II) complex, which is characterized by comprising the following steps:
A. adding metal Mn chloride, thiocyanate and methanol into a container, stirring at room temperature, adding benzyltriphenylphosphonium chloride into the solution, continuously stirring, and filtering to obtain a clear solution;
B. evaporating the obtained clear liquid at room temperature for 4-6 days to obtain the target product.
The synthetic route of the preparation method of the invention is as follows:
in a preferred embodiment of the invention, the stirring is carried out at room temperature for a period of 30 to 60 minutes
In a preferred embodiment of the invention, benzyltriphenylphosphonium chloride is added to the solution for an additional stirring time of 20 to 60 minutes.
In a preferred embodiment of the invention, it is characterized in that the molar ratio of the metal Mn chloride, thiocyanate and methanol is between 2 and 4.
The invention synthesizes the hybrid material at room temperature by taking metal chloride, benzyltriphenylphosphonium chloride and potassium thiocyanate as raw materials, and the material has excellent fluorescence property and important value in nonlinear optical property and information storage aspect.
Drawings
FIG. 1: example 1 [ BPP ] prepared 2 [Mn(NCS) 4 ]A crystal photograph of the material (the photograph was taken with a camera and the crystal size was about 3x 2.5x2mm).
FIG. 2 is a schematic diagram: powder X-ray diffraction pattern of the complex prepared in example 1.
FIG. 3: solid state fluorescence spectrum of the complex prepared in example 1.
FIG. 4 is a schematic view of: second order nonlinear optical effects of the complex prepared in example 1.
Detailed Description
The invention is further described in the following detailed description in conjunction with specific examples, which are intended to be illustrative, but not limiting, of the invention, and the methods and reagents used in the invention, as well as other alternatives and alternatives, which achieve the same technical result.
Example 1:
A. dissolving 0.198 g of manganese chloride solid and 0.389 g of thiocyanate solid in 5ml of methanol at a certain temperature (room temperature), and stirring for half an hour to obtain a clear solution A;
B. weighing 0.777 g of benzyltriphenylphosphonium chloride solid at room temperature, and dissolving in 10ml of methanol solution to obtain colorless clear solution B;
C. adding the solution B into the solution A, continuously stirring for half an hour to obtain a turbid liquid, filtering with medium-speed filter paper, standing the obtained supernatant at room temperature for 3-4 days, slowly evaporating to obtain pink granular crystals (shown in figure 1), which are the target products of the hybrid material (the target product is a single pure phase through single crystal X-ray diffraction and powder X-ray diffraction, shown in figure 2.)
At room temperature, the solid state fluorescence properties of the complexes were tested and analyzed (solid state fluorescence test on F-4600 type fluorescence spectrometer (Hitachi, japan), selecting a small number of samples to be tested on a quartz glass slide, for samples of unknown excitation wavelength, first selecting an excitation wavelength, then performing a full-band scan, taking the maximum value in the scanned emission spectrum, the maximum excitation peak of the complex being 248nm, and then measuring the emission peak at this excitation peak state.) FIG. 3 shows the ultraviolet spectrum between 340nm and 470nm, the results of exciting the complex at 248nm showing that [ (BPP) 2 Mn(NCS) 4 ]A strong emission band at 396nm is generated and the size of the peak is attributed to the Mn within the ligand 2+ Pi-pi transition of (c). Therefore, the complex can be used as a purple luminescent material.
This prompted the inventors to study their nonlinear optical properties, since the complexes have a non-centrosymmetric space group Cc. The second-order nonlinear optical effect of the complex is shown in fig. 4 (calibrating with potassium dihydrogen phosphate (KDP) on a nonlinear optical testing instrument, testing the complex, collecting data and processing the data), and the complex has strong SHG response (about 2 × KDP (KH)) through testing 2 PO 4 )). Therefore, the complex can be used as a second-order nonlinear optical material.
The above detailed description is only a preferred embodiment of the present invention, and should not be taken as limiting the invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the scope of the present invention. While the foregoing is directed to the preferred embodiment of the present invention, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (8)
1. A complex of the formula:
2. the complex of claim 1, which is a particulate crystal.
3. The complex of claim 2, the particulate crystals being pink particulate crystals.
4. Use of a complex according to any one of claims 1 to 3 as a fluorescent material and/or a nonlinear optical material.
5. A process for preparing a complex as claimed in any one of claims 1 to 3, characterized by comprising the steps of:
A. adding metal Mn chloride, thiocyanate and methanol into a container, stirring at room temperature, adding benzyltriphenylphosphonium chloride into the solution, continuously stirring, and filtering to obtain a clear solution;
B. evaporating the obtained clear liquid at room temperature for 4-6 days to obtain the target product.
6. The method according to claim 5, wherein the stirring time at room temperature is 30 to 60 minutes.
7. The method of claim 5, wherein the benzyltriphenylphosphonium chloride is added to the solution and the stirring is continued for 20 to 60 minutes.
8. The process according to claim 5, wherein the molar ratio of the metal Mn chloride, thiocyanate and methanol is from 2 to 4.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010110048.3A CN111171074B (en) | 2020-02-23 | 2020-02-23 | Benzyl triphenyl phosphine tetranuclear manganese (II) complex |
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| CN202010110048.3A CN111171074B (en) | 2020-02-23 | 2020-02-23 | Benzyl triphenyl phosphine tetranuclear manganese (II) complex |
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| CN111171074A CN111171074A (en) | 2020-05-19 |
| CN111171074B true CN111171074B (en) | 2022-10-18 |
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| CN113980060A (en) * | 2021-10-09 | 2022-01-28 | 四川大学 | Cadmium and manganese-based solid solution luminescent material and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512407A (en) * | 1994-12-07 | 1996-04-30 | Eastman Kodak Company | Bis(quaternary phosphonium) tetrahalomanganate salts as charge-control agents |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512407A (en) * | 1994-12-07 | 1996-04-30 | Eastman Kodak Company | Bis(quaternary phosphonium) tetrahalomanganate salts as charge-control agents |
Non-Patent Citations (3)
| Title |
|---|
| LI Yu-Kong等.Syntheses, Crystal Structures, SHG Response and Purple Luminescent Property of Tetra(isothiocyanate) Mn(II) and Substituted Benzyl Triphenylphosphonium Cations.《Chinese J.Struct.Chem.》.2021,第40卷(第6期),第739-745页. * |
| Qiang Li等.A Switchable Molecular Dielectric with Two Sequential Reversible Phase Transitions:[(CH3)4P]4[Mn(SCN)6].《Inorg.Chem.》.2015,第54卷第10642-10647页. * |
| 沈昊宇 等.一个含铜(II)四氮大环阳离子和锰(II)一维链阴离子化合物{[Cu(trans[14]diene)SCN]2Mn(SCN)4(4,4"-bipy).4H2O}n的合成和结构.《高等学校化学学报》.1998,第19卷(第10期),第1533-1536页. * |
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