CN104370839A - Oxygen ether-4-substituted bitriazole compound as well as preparation method and application of oxygen ether-4-substituted bitriazole compound - Google Patents

Oxygen ether-4-substituted bitriazole compound as well as preparation method and application of oxygen ether-4-substituted bitriazole compound Download PDF

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Publication number
CN104370839A
CN104370839A CN201410623861.5A CN201410623861A CN104370839A CN 104370839 A CN104370839 A CN 104370839A CN 201410623861 A CN201410623861 A CN 201410623861A CN 104370839 A CN104370839 A CN 104370839A
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triazole
preparation
compound
bitriazole
substituted
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王英
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Tianjin Normal University
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Tianjin Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses an oxygen ether-4-substituted bitriazole compound as well as a preparation method and application of the oxygen ether-4-substituted bitriazole compound, and particularly discloses 4-(4-(4-(4H-1, 2, 4-triazole-4-yl)phenoxyl)phenyl)-4H-1, 2, 4-triazole and a preparation method thereof. The organic compound is prepared by using a one-pot method, namely heating ethylenediamine, 1H-1, 2, 4-triazole, potassium carbonate, 4-(4-aminophenoxyl) phenylamine and copper iodide. The preparation method disclosed by the invention has the characteristics of simple technological operation, low production cost and little environmental pollution and is suitable for large-scale industrial production. The 4-(4-(4-(4H-1, 2, 4-triazole-4-yl)phenoxyl)phenyl)-4H-1, 2, 4-triazole prepared by using the preparation method can be applied to the aspect of luminescent agents.

Description

Oxygen ether-4-replaces two triazole compounds and preparation method thereof and application
The present invention obtains state natural sciences fund general project (21471113), and Tianjin Education Commission funded projects (20140506) and Tianjin innovation team of institution of higher education training plan subsidize (TD12-5038).
Technical field
The invention belongs to technical field of organic synthesis, relate to 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole compounds and its preparation method, 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1, the application of 2,4-triazole in luminous agent.
Background technology
4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole compounds has two dimensional structure.1,2,4-triazole and derivative thereof have the coordination feature of pyrazoles and imidazoles concurrently, are the bridgingligands that coordination ability is stronger, have synthesized at present and have characterized a large amount of monokaryons, multinuclear and multidimensional compound.These parts can with 1, nitrogen-atoms on 2 and metallic ion coordination form N1, N2-bridging pattern, for 4 unsubstituted 1,2,4-triazole derivative is by 2, nitrogen-atoms on 4 forms N2, N4-bridging pattern, this N2, N4-bridging pattern is with the N1 of imidazoles in metalloenzyme, and N3-bridging mode class seemingly.Special purpose for triazole class compounds also shows in the design of molecular device, and the metal complexes that synthesis has different dimension has been the vital step of device.
The present invention namely select 4-(4-amino-benzene oxygen) aniline be basic framework by simple organic reaction, design and synthesis novel to the two triazole species organism of benzene.4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole compounds luminescent material.
Up to now, not yet find 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2, this compound of 4-triazole compounds, do not retrieve relevant 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1, the bibliographical information of 2,4-triazole compounds synthetic method.
Summary of the invention
One object of the present invention is to provide a kind of 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole compounds and preparation method thereof.
Another object of the present invention is provide 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole and preparing the application in luminous agent.
The present inventor is surprised to find in test: with 4-(4-amino-benzene oxygen) aniline, 1H-1,2,4-triazole, salt of wormwood and cuprous iodide are main raw material(s), in reaction with DMF (DMF) for solvent, control temperature is when 80-200 DEG C, the high 4-of yield (4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1 can be obtained, 2,4-triazole.
Current inventor provides following technical scheme for this reason:
4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole compounds has following structure:
The preferred 4-of the present invention (4-amino-benzene oxygen) aniline, 1H-1,2,4-triazole, the mol ratio of salt of wormwood and cuprous iodide is 3:15:30:1; Temperature of reaction 80-200 DEG C, reaction times 12-120 hour.
 
Above reagent is all bought from Aladdin Reagent Company and is directly used.
The more detailed preparation method of the present invention is as follows:
A kind of 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2, the preparation method of 4-triazole is characterized in that, in polar solvent, adopt " one kettle way ", by 4-(4-amino-benzene oxygen) aniline, 1H-1,2,4-triazole, this organic compound prepared in a heated condition by salt of wormwood and cuprous iodide;
Polar solvent of the present invention is DMF.Described alkali is salt of wormwood.Wherein 4-(4-amino-benzene oxygen) aniline, 1H-1,2,4-triazole, the mol ratio of salt of wormwood and cuprous iodide is 3:15:30:1;
The advantage and disadvantage that 4-disclosed by the invention (4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole compounds has is:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) the phenyl)-4H-1 prepared by the present invention, 2,4-triazole may be used for luminous agent, and its production cost is low, profit margin is large, is more suitable for large-scale industrial production.
Accompanying drawing explanation
The nuclear-magnetism structure iron of Fig. 1: 4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole.
Embodiment
Below in conjunction with embodiment, the present invention is described further, and embodiment is only indicative, never means that it limits the scope of the invention by any way.All raw materials are all buy from chemical reagents corporation both domestic and external, through continuation purify but directly use.The fusing point of product is X in model 4the melting point apparatus of Micro carries out measure.Raw material used by the present invention is by commercially available.
 
Embodiment 1
4-(4-amino-benzene oxygen) aniline: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cuprous iodide is 3:15:30:1.
4-(4-amino-benzene oxygen) aniline (3 mmol) is added respectively in 50 mL, tri-mouthfuls of round-bottomed flasks that magneton, reflux exchanger and thermometer are housed, 1H-1,2,4-triazole (1.035 g, 15 mmol), salt of wormwood (4.14 g, 30 mmol), CuI (0.191 g, 1 mmol), 20 mL DMF.Start and be stirred in 100 DEG C, react 12 hours.After reaction terminates, reaction solution is down to room temperature, filter, filtrate adds 100 mL water, separates out and precipitates in a large number, suction filtration, collects filter cake, yield 46%.Ultimate analysis C 16h 12n 6o theoretical value: C, 63.15; H, 3.97; N, 27.62.Experimental value: C, 63.16; H, 3.94; N, 27.63.
Embodiment 2
Preparation method:
4-(4-amino-benzene oxygen) aniline: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cuprous iodide is 3:15:30:1
CuI (0.191 g is added respectively in 50 mL, tri-mouthfuls of round-bottomed flasks that magneton, reflux exchanger and thermometer are housed, 1 mmol), salt of wormwood (4.14 g, 30 mmol), 1H-1,2,4-triazole (1.035 g, 15 mmol), 4-(4-amino-benzene oxygen) aniline (0.99 g, 3 mmol), 20 mL DMF.Start and be stirred in 100 oc, reacts 12 hours.After reaction terminates, reaction solution is down to room temperature, filter, filtrate adds 100 mL water, separates out and precipitates in a large number, suction filtration, collects filter cake, yield 46%.Ultimate analysis C 16h 12n 6o theoretical value: C, 63.15; H, 3.97; N, 27.62.Experimental value: C, 63.16; H, 3.94; N, 27.63.
Embodiment 3
Luminous agent, has photoluminescent property; Concrete method steps is as follows:
By spectrophotofluorometer, carry out the excitation wavelength of this compound (embodiment 2) and the scanning of emission wavelength respectively, select and determine optimal wavelength.
Conclusion: the excitation wavelength of this compound and emission wavelength are respectively 375 nm and 550 nm.
After the preferred embodiment described in detail, be familiar with this technology personage can be well understood to, do not departing under above-mentioned claim and spirit and can carry out various change and amendment, all above embodiment is done according to technical spirit of the present invention any simple modification, equivalent variations and modification, all 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 specification sheets.

Claims (4)

1.4-(4-(4-(4H-1,2,4-triazole-4-yl) phenoxy group) phenyl)-4H-1,2,4-triazole compounds has following structure:
。
2. (4-(4-(the 4H-1 of 4-described in claim 1,2,4-triazole-4-yl) phenoxy group) phenyl) preparation method of-4H-1,2,4-triazole compounds, it is characterized in that adopting " one kettle way " at polar solvent, by 4-(4-amino-benzene oxygen) aniline (I), 1H-1,2,4-triazole (II), salt of wormwood and cuprous iodide react preparation in a heated condition; Wherein 4-(4-amino-benzene oxygen) aniline (I), 1H-1,2,4-triazole (II): salt of wormwood: the mol ratio of cuprous iodide, quadrol is 3:15:30:1; Temperature of reaction 80-200 oc, reaction times 12-120 hour;
(Ⅰ) (Ⅱ) 。
3. preparation method according to claim 2, wherein said polar solvent is DMF, and described alkali is salt of wormwood.
4.4-(4-(4-(4H-1,2, the 4-triazole-4-yl) phenoxy group) phenyl) application of-4H-1,2,4-triazole in luminous agent.
CN201410623861.5A 2014-11-10 2014-11-10 Oxygen ether-4-substituted bitriazole compound as well as preparation method and application of oxygen ether-4-substituted bitriazole compound Pending CN104370839A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104558055A (en) * 2015-02-26 2015-04-29 天津师范大学 Oxyether bistriazole nickel nitrate complex with potential fluorescent material and preparation method thereof
CN104592305A (en) * 2015-02-26 2015-05-06 天津师范大学 Manganese oxyether-bis(triazolyl) chloride complex used as potential fluorescent material and preparation method of manganese oxyether-bis(triazolyl) chloride complex
CN105524003A (en) * 2016-01-05 2016-04-27 天津师范大学 4-(4-(4-(4H-1,2,4-triazol-4-yl) phenoxy) phenyl)-4H-1,2,4-triazol-single crystal and application thereof
CN105646381A (en) * 2016-01-05 2016-06-08 天津师范大学 4-(4-(4H-1,2,4-triazole-4-yl)phenoxyl)phenyl)-4H-1,2,4-triazole mono-crystal

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103772305A (en) * 2014-01-14 2014-05-07 天津师范大学 Oxyether triazole compound, and preparation method and application thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103772305A (en) * 2014-01-14 2014-05-07 天津师范大学 Oxyether triazole compound, and preparation method and application thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104558055A (en) * 2015-02-26 2015-04-29 天津师范大学 Oxyether bistriazole nickel nitrate complex with potential fluorescent material and preparation method thereof
CN104592305A (en) * 2015-02-26 2015-05-06 天津师范大学 Manganese oxyether-bis(triazolyl) chloride complex used as potential fluorescent material and preparation method of manganese oxyether-bis(triazolyl) chloride complex
CN105524003A (en) * 2016-01-05 2016-04-27 天津师范大学 4-(4-(4-(4H-1,2,4-triazol-4-yl) phenoxy) phenyl)-4H-1,2,4-triazol-single crystal and application thereof
CN105646381A (en) * 2016-01-05 2016-06-08 天津师范大学 4-(4-(4H-1,2,4-triazole-4-yl)phenoxyl)phenyl)-4H-1,2,4-triazole mono-crystal

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Application publication date: 20150225