CN104370965B - Three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound and preparation method thereof and application - Google Patents
Three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound and preparation method thereof and application Download PDFInfo
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- CN104370965B CN104370965B CN201410623854.5A CN201410623854A CN104370965B CN 104370965 B CN104370965 B CN 104370965B CN 201410623854 A CN201410623854 A CN 201410623854A CN 104370965 B CN104370965 B CN 104370965B
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Abstract
The invention discloses a kind of three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus and three (4-(1H-1 thereof, 2,4-triazol-1-yl) phenyl) preparation method of phosphorus, it is to adopt " one kettle way ", i.e. ethylenediamine, 1H-1,2,4-triazoles, potassium carbonate, trifluoro-benzene base phosphorus, this organic compound is prepared in Hydro-Giene (Water Science). heating. It is simple that the preparation method of the present invention has technological operation, and production cost is low, the feature that environmental pollution is little, is suitable for large-scale industrial production. Three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound prepared by the present invention can be applied in luminous agent.
Description
The present invention obtains state natural sciences fund general project (21471113), Tianjin Education Commission funded projects (20140506) and Tianjin innovation team of institution of higher education training plan and subsidizes (TD12-5038).
Technical field
The invention belongs to technical field of organic synthesis, relate to three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound and their preparation method three (4-(1H-1,2,4-triazol-1-yls) phenyl) phosphorus compound prepares the application of luminous agent aspect.
Background technology
Three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus has tripod structure. 1,2,4-triazole and derivant thereof have the coordination feature of pyrazoles and imidazoles concurrently, are the bridging ligands that coordination ability is stronger, have synthesized and characterized substantial amounts of monokaryon, multinuclear and multidimensional compound at present. These parts can with 1, nitrogen-atoms on 2 forms N1 with metallic ion coordination, N2-bridge gang mould formula, for 4 unsubstituted 1,2,4-triazole derivative can pass through 2, nitrogen-atoms on 4 forms N2, N4-bridge gang mould formula, this N2, N4-bridge gang mould formula is similar with N1, the N3-bridge gang mould formula of imidazoles in metalloenzyme. Specific use for triazole class compounds is also manifested by the design of molecular device, and it has been the vital step of device that synthesis has the metal complex of different dimension.
Namely the present invention selects trifluoro-benzene base phosphorus to be that basic framework is by simple organic reaction, three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus Organic substance of design and synthesis novelty. Up to now, not yet find three (4-(1H-1,2,4-triazol-1-yl) phenyl) this compound of phosphorus, do not retrieve the bibliographical information of relevant three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus synthetic method.
Summary of the invention
It is an object of the present invention to provide a kind of three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound and preparation method thereof.
Offer three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus and the application in luminous agent thereof are provided.
The present inventor has found surprisingly that in test with trifluoro-benzene base phosphorus, 1H-1,2,4-triazoles, potassium carbonate and Hydro-Giene (Water Science). are main raw material(s), with N in reaction, dinethylformamide (DMF) is solvent, controls temperature when 80-200 DEG C, it is possible to obtain the three (4-(1H-1 that yield is high, 2,4-triazol-1-yls) phenyl) phosphorus compound.
Following technical scheme is current inventor provides for this:
Three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound has following structure:
Three (4-(1H-1 of the present invention, 2,4-triazol-1-yl) phenyl) preparation method of phosphorus, its feature is adopting " one kettle way ", in polar solvent, by trifluoro-benzene base phosphorus, 1H-1,2,4-triazoles, potassium carbonate and copper oxide prepare this organic compound in a heated condition; Wherein trifluoro-benzene base phosphorus: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of copper oxide is 3:15:30:1;
The preferred trifluoro-benzene base phosphorus of the present invention, 1H-1,2,4-triazoles, the mol ratio of potassium carbonate and Hydro-Giene (Water Science). is 3:15:30:1; Reaction temperature 80-200 DEG C, 12-120 hour response time.
The more detailed preparation method of the present invention is as follows:
A kind of three (4-(1H-1,2,4-triazol-1-yl) phenyl) preparation method of phosphorus is characterized in that, in polar solvent, adopt " one kettle way ", by trifluoro-benzene base phosphorus, 1H-1, this organic compound prepared in a heated condition by 2,4-triazoles, potassium carbonate and Hydro-Giene (Water Science).;
Polar solvent of the present invention is DMF. Described alkali is potassium carbonate. Wherein trifluoro-benzene base phosphorus, 1H-1,2,4-triazoles, the mol ratio of potassium carbonate and Hydro-Giene (Water Science). is 3:15:30:1;
Three (4-(1H-1,2,4-triazol-1-yl) phenyl) disclosed by the invention phosphorus compound have the advantage that and being characterized in that:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) three (4-(1H-1,2, the 4-triazol-1-yl) phenyl) phosphorus prepared by the present invention may be used for luminous agent, and its production cost is low, and profit margin is big, is more suitable for large-scale industrial production.
Accompanying drawing explanation
The nuclear magnetic data figure of Fig. 1: three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described further, and embodiment is only indicative, is in no way to be construed as the scope that it is intended to limit the present invention in any manner. All of raw material is all buy from chemical reagents corporation both domestic and external, it does not have through continuation purify but directly use. The fusing point of product is to be X in model4Measurement on the melting point apparatus of Micro. Wherein trifluoro-benzene base phosphorus, 1H-1,2,4-triazole, potassium carbonate, Hydro-Giene (Water Science). is by commercially available.
Embodiment 1
Trifluoro-benzene base phosphorus: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of Hydro-Giene (Water Science). is 3:15:30:1.
It is separately added into trifluoro-benzene base phosphorus (3mmol) in equipped with tri-mouthfuls of round-bottomed flasks of 50mL of magneton, reflux condenser and thermometer, 1H-1,2,4-triazole (1.035g, 15mmol), potassium carbonate (4.14g, 30mmol), CuI (0.191g, 1mmol), 20mLDMF. Start stirring at 100 DEG C, react 12 hours. Reactant liquor is down to room temperature after terminating by reaction, filters, and filtrate adds 100mL water, precipitates out a large amount of precipitation, sucking filtration, collects filter cake, yield 66%. Elementary analysis C24H18N9P theoretical value: C, 62.20; H, 3.91; N, 27.20. Experiment value: C, 62.26; H, 3.94; N, 27.23.
Embodiment 2
Luminous agent, has photoluminescent property; Concrete method step is as follows:
By spectrofluorophotometer, carry out the excitation wavelength of this compound (embodiment 1) respectively and launch the scanning of wavelength, select and determine optimal wavelength.
Conclusion: the excitation wavelength of this compound and transmitting wavelength respectively 375nm and 550nm.
After the preferred embodiment described in detail, it is familiar with this skilled worker to be clearly understood that, various change and amendment can be carried out under without departing from above-mentioned claim and spirit, all any simple modification, equivalent variations and modifications above example made according to the technical spirit of the present invention, belong to the scope of technical solution of the present invention. And the present invention is not also by the restriction of example embodiment in description.
Claims (4)
1. three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound has following structure:
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2. three (4-(1H-1 described in claim 1,2,4-triazol-1-yl) phenyl) preparation method of phosphorus compound, it is characterized in that adopting " one kettle way " at polar solvent, by trifluoro-benzene base phosphorus (I), 1H-1,2,4-triazole (II), potassium carbonate and Hydro-Giene (Water Science). react preparation in a heated condition; Wherein trifluoro-benzene base phosphorus (I), 1H-1,2,4-triazoles (II), the mol ratio of potassium carbonate and Hydro-Giene (Water Science). is 3:15:30:1; Reaction temperature 80-200oC, 12-120 hour response time;
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3. the preparation method described in claim 2, wherein said polar solvent is DMF.
4. three (4-(1H-1,2,4-triazol-1-yl) phenyl) phosphorus compound application in preparing luminous agent.
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| CN107306964A (en) * | 2016-04-27 | 2017-11-03 | 天津师范大学 | Application of the compound based on triazole in anti-wheat sharp eyespot opportunistic pathogen medicine is prepared |
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| US3141023A (en) * | 1961-08-23 | 1964-07-14 | Du Pont | Certain nu-carbamylurazoles |
| US4767552A (en) * | 1986-06-23 | 1988-08-30 | The Lubrizol Corporation | Urazole compositions useful as additives for functional fluids |
| CN100503771C (en) * | 2005-06-28 | 2009-06-24 | 友达光电股份有限公司 | Luminescent material, and organic electro photoluminescence module wing same |
| CN101747373B (en) * | 2010-01-20 | 2013-04-10 | 中国科学院长春应用化学研究所 | Carbazole compound, organic electroluminescence device containing carbazole compound and preparation method thereof |
| CN103468246B (en) * | 2013-09-04 | 2016-05-11 | 吉林奥来德光电材料股份有限公司 | A kind of luminous organic material, its preparation method and electroluminescent device thereof containing 1,2,4-triazole |
| CN103833776A (en) * | 2014-03-06 | 2014-06-04 | 天津师范大学 | Cuprous dinuclear complex in blending of diimine ligand and alkyne biphosphine ligand and preparation method and application of cuprous dinuclear complex |
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