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A kind of solid broadband red light emitting organic luminescent material and preparation method thereof

A luminescent material, solid-state technology, applied in luminescent materials, material analysis by optical means, analysis of materials, etc., can solve the application research of live cell imaging that does not involve solid-state fluorescence emission characteristics, the cyclohexanone structure has few targets, and the structure Problems such as poor modifiability, to achieve the effect of promoting solid-state luminescence properties, good up-conversion fluorescence properties, and stable molecular structure

Active Publication Date: 2018-07-27
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this research work is very limited, only one compound has been developed, and it is limited to cyclohexanone compounds, let alone the application research on solid-state fluorescence emission characteristics and live cell imaging
Therefore, there are still many deficiencies such as few varieties, single function, few structural targets of cyclohexanone, poor structural modification, etc., and further development and research are urgently needed

Method used

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  • A kind of solid broadband red light emitting organic luminescent material and preparation method thereof
  • A kind of solid broadband red light emitting organic luminescent material and preparation method thereof
  • A kind of solid broadband red light emitting organic luminescent material and preparation method thereof

Examples

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Effect test

Embodiment 1

[0042] 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)-4-piperidone (Compound I) preparation:

[0043] In a 250 ml round bottom flask, mix 4-piperidone (compound III, 1 mmol) and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)propene Aldehyde (compound II, 2 mmol) was dissolved in 50 ml of ethanol, 10 ml of 15% potassium hydroxide solution 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, neutralized to neutral with glacial acetic acid, 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-acetone mixed solvent and dried in vacuum to obtain a red solid with a yield of 76%.

[0044] 1H NMR (300MHz, CDCl3 / TMS) δ: 1.69 (d, J = 6.9Hz, 12H), 3.55 (s, 4H), 4.85-4.95 (m, 2H), 6.43 (dd, J = 12.0, 15.3Hz, 2H), 7.04-...

Embodiment 2

[0046] 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)-4-piperidone (Compound I) preparation:

[0047] In a 250 ml round bottom flask, mix 4-piperidone (compound III, 1 mmol) and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)propene Aldehyde (compound II, 2.2 mmol) was dissolved in 50 ml of methanol, 20 ml of 20% sodium hydroxide solution was added dropwise to the solution under rapid stirring, and the reaction was stirred at room temperature for 15 hours. Afterwards, the reaction solution was poured into 150 ml of water, neutralized to neutral with 36% acetic acid by mass fraction, 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 red solid with a yield of 78%.

Embodiment 3

[0049] 3,5-bis(3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)allylidene)-4-piperidone (Compound I) preparation:

[0050] In a 250 ml round bottom flask, mix 4-piperidone (compound III, 1 mmol) and 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)propene Aldehyde (compound II, 2 mmol) was dissolved in 50 ml of methanol, 15 ml of 18% potassium hydroxide solution was added dropwise to the solution under rapid stirring, and the reaction was stirred at room temperature for 12 hours. Afterwards, the reaction solution was poured into 150 ml of water, neutralized to neutral with glacial acetic acid, 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-acetone mixed solvent and dried in vacuum to obtain a red solid with a yield of 75%.

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Abstract

The invention discloses a difunctional solid-state broadband red light emission organic light-emitting material having a structure shown in a formula I and a preparation method thereof. According to the solid-state broadband red light emission organic light-emitting material and the preparation method thereof disclosed by the invention, novel solid-state broadband red light emission piperidone organic light-emitting material with upconversion fluorescence characteristic are formed by combining piperidone with fluoro-phenylindole functional structure units through polyene bridged bonds. The difunctional solid-state broadband red light emission organic light-emitting materials provided by the invention have the characteristics of solid-state broadband red light emission and upconversion fluorescence, stable molecular structure, multiple functions, convenience in use and high practicality. (The formula I is shown in the description).

Description

Technical field: [0001] The invention relates to the technical field of organic luminescent materials, in particular to a solid broadband red light emitting organic luminescent material and a preparation method thereof. Background technique: [0002] Organic light-emitting materials are widely used in many fields such as organic fluorescent sensors, organic optoelectronic devices, and bioluminescent imaging. The most prominent feature of organic light-emitting materials is that they can convert various forms of absorbed energy into optical radiation. One of the key issues to be solved in the development of organic light-emitting materials is how to improve the solid-state emission properties of organic materials, because in most cases, although organic light-emitting materials show strong fluorescence in dilute solutions, they often fluoresce in solid or aggregated states. Quenching, there is only weak fluorescence or almost no light, which limits the application of organic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C09K11/06G01N21/64
CPCC07D401/14C09K11/06C09K2211/1029G01N21/6486
Inventor 马艳芳陈智勇孙一峰叶小机汪昭玮张译方柳亚玲牟德海
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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