A quinuclidone compound, its application as a solid-state green light-emitting organic luminescent material and its preparation method

A technology of quinuclidinone and quinuclidinone hydrochloride is applied in the field of organic light-emitting materials to achieve the effects of improving absorption and transmission speed, improving processing performance and practicability, and reducing coplanarity

Active Publication Date: 2020-10-30
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although quinuclidone derivatives have been paid attention to by researchers and a large number of studies have been carried out, the research on this type of compounds in the prior art is mostly limited to synthetic methods, process research, and their use as pharmaceutical intermediates in drug synthesis. application, but there are very few reports on the preparation and application research of organic light-emitting materials

Method used

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  • A quinuclidone compound, its application as a solid-state green light-emitting organic luminescent material and its preparation method
  • A quinuclidone compound, its application as a solid-state green light-emitting organic luminescent material and its preparation method
  • A quinuclidone compound, its application as a solid-state green light-emitting organic luminescent material and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: 2-(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)-3-quinuclidinone (I) preparation of

[0029] In a 250 mL round bottom flask, mix 3-quinuclidone hydrochloride (1 mmol) and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)propene Aldehyde (1 mmol) was dissolved in 100 mL of ethanol, 15 mL of potassium hydroxide solution with a mass fraction of 15% was added dropwise to the solution under rapid stirring, and the reaction was stirred at room temperature for 10 hours. Afterwards, the reaction solution was poured into 150 mL of water and left to stand, and the resulting solid was filtered under reduced pressure, washed with water several times, and dried at room temperature. Recrystallized from ethanol and dried in vacuo to obtain a yellow solid with a yield of 73%.

[0030] The obtained product was determined to be the target product by proton nuclear magnetic resonance spectrum, carbon nuclear magnetic resonance spectrum, and mass spectrometry. T...

Embodiment 2

[0032] Example 2: 2-(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)-3-quinuclidinone (I) preparation of

[0033] In a 250 mL round bottom flask, mix 3-quinuclidone hydrochloride (1 mmol) and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)propene Aldehyde (1.1 mmol) was dissolved in 100 mL of methanol, 20 mL of 25% sodium hydroxide solution was added dropwise to the solution under rapid stirring, and the reaction was stirred at room temperature for 9 hours. Afterwards, the reaction solution was poured into 150 mL of water and left to stand, and the resulting solid was filtered under reduced pressure, washed with water several times, and dried at room temperature. Recrystallized from ethanol and dried in vacuo to obtain a yellow solid with a yield of 77%.

Embodiment 3

[0034] Example 3: 2-(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)-3-quinuclidinone (I) preparation of

[0035]In a 250 mL round bottom flask, mix 3-quinuclidone hydrochloride (1 mmol) and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)propene Aldehyde (1.1 mmol) was dissolved in 100 mL of methanol, 15 mL of 20% potassium hydroxide solution was added dropwise to the solution under rapid stirring, and the reaction was stirred at room temperature for 13 hours. Afterwards, the reaction solution was poured into 150 mL of water and left to stand, and the resulting solid was filtered under reduced pressure, washed with water several times, and dried at room temperature. Recrystallized from ethanol and dried in vacuo to obtain a yellow solid with a yield of 76%.

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Abstract

The invention discloses a quinuclidine ketone compound as shown in a formula I. According to the compound, two functional structural units: quinuclidine ketone and fluorobenilindole are combined through a polyenoid bridge bond to form a novel quinuclidine ketone solid state green emitting organic light-emitting material. The invention provides a novel application of the compound and develops a novel light-emitting molecular framework. The compound, as the quinuclidine ketone solid state green emitting organic light-emitting material, is applied to the fields of light-emitting apparatuses, laser dyes, fluorescence sensation and anti-counterfeit technologies and biomedicine analysis. The formula is as shown in the description.

Description

Technical field: [0001] The invention relates to the technical field of organic luminescent materials, in particular to a quinuclidone compound, its application as a solid-state green light emitting organic luminescent material and a preparation method thereof. Background technique: [0002] Organic light-emitting materials are widely used in organic electroluminescence devices, organic solid-state lasers, organic photovoltaic cells, biomedical fluorescence imaging, organic fluorescence sensors, and anti-counterfeiting materials. The research and development of multicolor solid-state fluorescence-emitting organic light-emitting materials is a research hotspot in the field of optoelectronic materials and technology. [0003] Quinuclidone is an important intermediate of cevimeline, solifenacin succinate, azasetron, mequitazine, palonosetron and other drugs. Although quinuclidone derivatives have been paid attention to by researchers and a large number of studies have been car...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D453/02C09K11/06
CPCC07D453/02C09K11/06C09K2211/1007C09K2211/1029
Inventor 孙一峰张译方管啸晓魏俊锋汪昭玮谢宇达刘梦影李天龙钱友荣牟德海
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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