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Tris(4-triazole phenyl) amine compound as well as preparation method and application thereof

A technology of triazole phenyl and amine compounds, which is applied in the application field of tris(4-triazole phenyl) amine for preparing optoelectronic materials, and can solve the problem that tris (4-triazole phenyl) amine has not been found, and the search has not yet been carried out. To the problems such as the bibliographical report of the three (4-triazole phenyl) amine synthetic method, reach the effect that the reaction operation is simple and easy, suitable for large-scale industrial production, and the production cost is low

Inactive Publication Date: 2012-08-15
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the compound of tris(4-triazolephenyl)amine has not been found yet, let alone the literature reports on the synthesis method of tris(4-triazolephenyl)amine

Method used

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  • Tris(4-triazole phenyl) amine compound as well as preparation method and application thereof
  • Tris(4-triazole phenyl) amine compound as well as preparation method and application thereof
  • Tris(4-triazole phenyl) amine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Tris(4-iodophenyl)amine: triazole: potassium carbonate: the molar ratio of copper oxide is 2:10:30:1

[0031] Add CuO (0.0398 mg, 0.5 mmol), potassium carbonate (2.0731 g, 15 mmol), triazole (0.345 mg, 5 mmol), triazole ( 4-iodophenyl)amine (0.6230 g, 1 mmol), 20 mL DMF. Start stirring at 100 o C, reacted for 24 hours. After the reaction, the reaction liquid was lowered to room temperature, filtered, and 100 mL of water was added to the filtrate, and a large amount of precipitate was precipitated, filtered with suction, and the filter cake was collected, with a yield of 78.3%. Anal. Calcd for C 24 h 20 N 10 O: C, 62.06; H, 4.34; N, 30.16. Found: C, 62.31; H, 4.64; N, 30.23.

Embodiment 2

[0033] Preparation:

[0034] Tris(4-iodophenyl)amine: triazole: potassium carbonate: the molar ratio of copper oxide is 2:15:30:1

[0035] Add CuO (0.0398 mg, 0.5 mmol), potassium carbonate (2.0731 g, 15 mmol), triazole (0.345 mg, 5 mmol), triazole ( 4-iodophenyl)amine (0.6230 g, 1 mmol), 20 mL DMF. Start stirring at 150 o C reacted for 60 hours. After the reaction, the reaction liquid was lowered to room temperature, filtered, and 100 mL of water was added to the filtrate, and a large amount of precipitate was precipitated, filtered by suction, the filter cake was collected, and recrystallized with water to obtain a single crystal of tris(4-triazolephenyl)amine with a yield of 78.3%. .

[0036] Anal. Calcd for C 24 h 20 N 10 O: C, 62.06; H, 4.34; N, 30.16. Found: C, 62.31; H, 4.64; N, 30.23.

[0037] The crystal structure was determined using an APEX II CCD area detector, using graphite monochromatized Mokα rays (l = 0.71073 ?) as the incident radiation, and w-2q Di...

Embodiment 3

[0042] Practical examples of the use of dyes or luminescent agents

[0043] Method: The differential pulse voltammetry (DPV) curve of the dye solution was measured by the PARSTAT 2273 electrochemical workstation developed by the Princeton Institute of Applied Research. The DPV test of the solution adopts a three-electrode system, the glassy carbon electrode is the working electrode, the auxiliary electrode is the platinum plate electrode, and the self-made Ag / AgNO3 electrode is the reference electrode; the electrolyte is the acetonitrile solution of 0.1mol·L-1TBAP. Using the ferrocene redox reversible point pair as the internal standard, the calibration value between the test system and the standard hydrogen electrode system was obtained.

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Abstract

The invention discloses a tris(4-triazole phenyl) amine compound and single crystal and a preparation method of tris(4-triazole phenyl) amine. The organic compound is prepared by adopting a one-pot method, namely heating tris(4-iodobenzene) amine, triazole, potassium carbonate and copper oxide. The preparation method has the characteristics of simple process operation, low production cost and low environmental pollution, and is suitable for large-scale industrial production. The prepared tris(4-triazole phenyl) amine single crystal can be applied to photoelectric materials, in particular to dyes and luminescence agents.

Description

[0001] The invention was funded by Tianjin Municipal Science and Technology Commission General Project (11JCYBJC03600), National Natural Science Foundation of China-China Youth Fund (21001080), Talent Introduction Project of Tianjin Normal University (5RL090) and Tianjin Normal University Development Fund (52X09042). technical field [0002] The invention belongs to the technical field of organic synthesis, and relates to tris(4-triazolephenyl)amine compounds and their single crystals, their preparation methods, and the application of tris(4-triazolephenyl)amine in the preparation of photoelectric materials. Background technique [0003] Triphenylamine and its derivatives are a class of optoelectronic materials with excellent performance. They are non-planar aromatic amine compounds with a propeller-like space structure, and their special space structure weakens the aggregation degree of triphenylamine-based dye molecules. 1,2,4-triazole and its derivatives have the coordinat...

Claims

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Application Information

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IPC IPC(8): C07D249/08C09B57/00C09K11/06H01G9/20H01G9/042H01L51/46
CPCY02E10/549
Inventor 王英刘巨艳
Owner TIANJIN NORMAL UNIVERSITY
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