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Phenoxyl tritriazole compound, preparation method and applications thereof

A technology of triazole compound and phenoxy, applied in the field of organic synthesis, can solve the problem of high cost and achieve the effects of low production cost, high reaction yield and high purity

Inactive Publication Date: 2015-03-11
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]Among the reported dye sensitizers, the ruthenium-based sensitizer containing precious metals has the best performance, but its cost is relatively high

Method used

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  • Phenoxyl tritriazole compound, preparation method and applications thereof
  • Phenoxyl tritriazole compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of 4-(3,5-bis(4-aminophenoxy)phenoxy)aniline (I)

[0023] Add 6 g of phloroglucinol, 10 mL of p-fluoronitrobenzene, 20 mL of DMF to reflux for 3 hours, cool to room temperature, add 100 mL of water, and filter with suction to obtain a brown crude product. Washing with a small amount of methanol afforded III as a tan solid.

[0024]

[0025]

[0026] Add 5 g of compound III, 1 g of iron powder and 100 mL of ethanol solution into a 250 mL three-neck flask, add 10 mL of ethanol while stirring, and reflux for 10 hours. Continue to stir for 5 hours after cooling, and filter with suction. The solid was extracted with CHCl3. The extract was dried and then evaporated to obtain a light yellow solid powder which was 4-(3,5-bis(4-aminophenoxy)phenoxy)aniline (compound I)

[0027]

Embodiment 2

[0029] 4-(3,5-bis(4-aminophenoxy)phenoxy)aniline, the molar ratio of bisformylhydrazide is 1:3

[0030] Add 4-(3,5-bis(4-aminophenoxy)phenoxy)aniline (1 mmol), diformyl Hydrazine (2 mmol) was stirred at 160°C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and a large amount of precipitate was precipitated, which was recrystallized with water and ethanol, and the yield was 86%. Elemental Analysis C 24 h 21 N 3 o 3 Theoretical: C, 72.17; H, 5.30; N, 10.52. Experimental values: C, 72.19; H, 5.38; N, 10.53.

[0031] Preparation:

[0032] The molar ratio of 4-(3,5-bis(4-aminophenoxy)phenoxy)aniline to bisformylhydrazide is 1:2.

[0033] Add 4-(3,5-bis(4-aminophenoxy)phenoxy)aniline (1 mmol), diformyl Hydrazine (2 mmol) was stirred at 160°C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and a large amount of precipitate was precipitated, which was recrystallized wi...

Embodiment 3

[0035] The luminescent agent has fluorescent properties; the specific method steps are as follows:

[0036] Scan the excitation wavelength and emission wavelength of the compound (Example 1) with a spectrofluorometer to select and determine the optimum wavelength.

[0037] Conclusion: The excitation and emission wavelengths of this compound are 375 nm and 550 nm, respectively.

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PUM

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Abstract

The invention provides a phenoxyl tritriazole compound, a preparation method and applications thereof. The invention discloses a preparation method of 4-(4-(3,5-di(4-(4H-1,2,4-triazole-4-yl)phenoxyl)phenoxyl)phenyl)-4H-1,2,4-triazole. The compound is prepared by a one-pot method, namely heating 4-(3,5-di(4-aminophenoxyl)phenoxyl)aniline and diformyl hydrazine to prepare the compound. The preparation method has the characteristics of simple operation, low production cost, and little environment pollution, and is suitable for massive industrial production. The prepared 4-(4-(3,5-di(4-(4H-1,2,4-triazole-4-yl)phenoxyl)phenoxyl)phenyl)-4H-1,2,4-triazole can be applied to fields of photoelectric materials and luminescent agents.

Description

[0001] The invention is supported by the General Project of National Natural Science Foundation of China (21471113), the project funding of Tianjin Municipal Education Commission (20140506) and the funding of Tianjin Higher Education Innovation Team Training Program (TD12-5038). technical field [0002] The invention belongs to the technical field of organic synthesis and relates to 4-(4-(3,5-bis(4-(4H-1,2,4-triazol-4-yl)phenoxy)phenoxy)phenyl) -4H-1,2,4-triazole compound and its preparation method, 4-(4-(3,5-bis(4-(4H-1,2,4-triazol-4-yl)phenoxy Application of base)phenoxy)phenyl)-4H-1,2,4-triazole in luminescent agent. Background technique [0003] 4-(4-(3,5-bis(4-(4H-1,2,4-triazol-4-yl)phenoxy)phenoxy)phenyl)-4H-1,2,4- Triazoles have a tripod structure. 1,2,4-triazole and its derivatives have the coordination characteristics of pyrazole and imidazole, and are bridging ligands with strong coordination ability. A large number of mononuclear, polynuclear and multidimension...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C09B57/00
CPCC07D249/08C09B57/00
Inventor 王英
Owner TIANJIN NORMAL UNIVERSITY
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