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Imidazole tri-acylhydrazone compound, application of compound as organic light-emitting material as well as preparation method of compound

A technology of imidazole triacylhydrazone and luminescent materials, which is applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of few varieties of organic luminescent materials and cannot meet application requirements, and achieve reduced interaction, stable structure, The effect of reducing coplanarity

Active Publication Date: 2015-11-18
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although imidazole and acylhydrazone compounds have received great attention from researchers and extensive research has been carried out, there are still few types of organic light-emitting materials with solid-state light-emitting properties, which cannot meet the application requirements of related fields.
On the other hand, there are few studies on triacylhydrazone and polyacylhydrazone compounds. In particular, imidazole is used as the basic functional structural unit, and functional groups such as acylhydrazone, naphthyl and diarylvinyl are introduced to form Multifunctional base imidazole triacylhydrazone compounds, and investigate the research on aspects such as its photophysical properties, there is no report in the prior art

Method used

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  • Imidazole tri-acylhydrazone compound, application of compound as organic light-emitting material as well as preparation method of compound
  • Imidazole tri-acylhydrazone compound, application of compound as organic light-emitting material as well as preparation method of compound
  • Imidazole tri-acylhydrazone compound, application of compound as organic light-emitting material as well as preparation method of compound

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Embodiment 1

[0032] Embodiment 1: the preparation of imidazole triacylhydrazone (compound I)

[0033] (1) Preparation of intermediate imidazole tricarboxylate (compound III)

[0034] In a dry 100 ml round bottom flask, add dimethyl 4,4'-(3,4-dioxo-1,5-hexadiene-1,6-diyl)dibenzoate (Compound IV) (0.003mol), methyl 4-formylbenzoate (Compound V) (0.003mol), ammonium acetate (0.03mol), and 30 ml of anhydrous acetic acid were refluxed for 8 hours under rapid stirring. After cooling to room temperature, the reaction solution was poured into ice water under rapid stirring, and the pH was adjusted to 7 with ammonia water. The resulting solid was filtered under reduced pressure, washed with water several times, and dried at room temperature. Recrystallized from a mixed solvent of ethanol-N,N-dimethylformamide and dried in vacuum to obtain a yellow powder with a yield of 71%. The melting point is 178–180°C.

[0035] (2) Preparation of intermediate imidazole triformyl hydrazide (compound II)

[0...

Embodiment 2

[0041] Embodiment 2: the preparation of imidazole triacylhydrazone (compound I):

[0042] (1) Preparation of intermediate imidazole tricarboxylate (compound III)

[0043] In a dry 100 ml round bottom flask, add dimethyl 4,4'-(3,4-dioxo-1,5-hexadiene-1,6-diyl)dibenzoate (Compound IV) (0.003mol), methyl 4-formylbenzoate (Compound V) (0.003mol), ammonium acetate (0.03mol), and 30 ml of anhydrous acetic acid were refluxed for 8 hours under rapid stirring. After cooling to room temperature, the reaction solution was poured into ice water under rapid stirring, and the pH was adjusted to 7 with 10% aqueous sodium hydroxide solution. The resulting solid was filtered under reduced pressure, washed with water several times, and dried at room temperature. Recrystallize from a mixed solvent of ethanol-N,N-dimethylformamide, and dry in vacuo to obtain a yellow powder. The melting point is 178–180°C.

[0044] (2) Preparation of intermediate imidazole triformyl hydrazide (compound II)

...

Embodiment 3

[0048] Embodiment 3: Fluorescence performance test of imidazole triacylhydrazone (compound I)

[0049] It is 2 * 10 that the compound of embodiment 1 is formulated into concentration -5 M tetrahydrofuran solution. Measure its ultraviolet absorption and fluorescence properties on a HORIBA JobinYvonAqualog absorption and three-dimensional fluorescence scanning spectrometer with a 1 cm fluorescence cell, the results are as follows figure 1 and 2 shown. The solid-state fluorescence spectrum is measured with a PerkinElmer LS-55 fluorescence spectrophotometer, the results are shown in image 3 .

[0050] Simultaneously observe the fluorescent color of the solid powder of Compound I obtained in Example 1 and its tetrahydrofuran solution under the irradiation of a 365 nm ultraviolet lamp. The results show that under the irradiation of 365nm ultraviolet lamp, compound I emits strong blue-green fluorescence in solution, and emits strong yellow fluorescence in solid state.

[0051]...

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Abstract

The invention discloses an imidazole tri-acylhydrazone compound shown in formula I, an application of the compound as an organic light-emitting material as well as a preparation method of the compound. Four functional structure units, namely, an imidazole group, an acylhydrazone group, a diarylethene group and a naphthyl group, are effectively combined in one molecule, and a novel multi-functional-group imidazole tri-acylhydrazone organic light-emitting molecule is formed. The preparation method of the light-emitting material comprises steps as follows: (1) preparation of an intermediate, namely, imidazole trimethyl tricarboxylate; (2) preparation of an intermediate, namely, imidazole trimethyl hydrazide; (3) preparation of a target product, the imidazole tri-acylhydrazone. The preparation method is simple and comprises few synthesis steps, raw materials are easy to obtain, the cost is low, and purification and industrialization are easy. The imidazole tri-acylhydrazone compound is stable in structure and easy to store and shows stronger fluorescence emission under solution and solid states. The light-emitting material is good in stability and can be applied to fields of light-emitting devices, fluorescence sensing and the like.

Description

Technical field: [0001] The invention relates to the technical field of organic luminescent materials, in particular to an imidazole triacylhydrazone compound, its application as an organic luminescent material and its preparation method. Background technique: [0002] Organic light-emitting materials are widely used in many fields such as organic optoelectronics and organic fluorescent sensors. Designing and synthesizing organic light-emitting materials with high fluorescence efficiency and adjustable wavelength is an important research topic in this field, and it is also a very challenging and challenging task. important work. [0003] One of the hot issues in the research of organic light-emitting materials is how to improve the solid-state emission properties of materials, because in most cases, although organic light-emitting materials show strong fluorescence in dilute solutions, fluorescence quenching often occurs in solid-state or aggregated states. Then there is on...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64C09K11/06
CPCC07D233/64C09K11/06C09K2211/1044
Inventor 马艳芳陈智勇孙一峰李兴吉国强宋玉梅陈江韩
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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