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Small molecular material with yellow mechanoluminescence of 10-membered fused ring benzothiadiazole as well as preparation method and application of small molecular material

A benzothiadiazole and luminescent technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., to achieve the effect of small interference and sensitive brightness

Active Publication Date: 2021-11-02
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has also been shown that if the molecules are packed too tightly, the crystals are not easily broken due to their strong rigidity, which instead leads to weaker ML

Method used

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  • Small molecular material with yellow mechanoluminescence of 10-membered fused ring benzothiadiazole as well as preparation method and application of small molecular material
  • Small molecular material with yellow mechanoluminescence of 10-membered fused ring benzothiadiazole as well as preparation method and application of small molecular material
  • Small molecular material with yellow mechanoluminescence of 10-membered fused ring benzothiadiazole as well as preparation method and application of small molecular material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Synthesis of compound C4

[0075] The synthetic route is as follows:

[0076]

[0077] The preparation method of C4, its main steps are:

[0078] 1) 4,8-diketone-benzo[1,2-b:4,5-b']dithiophene (5.0g, 22.7mmol) was dissolved in 50mL ethanol, and sodium borohydride (3.4 g, 90.8 mmol), after the addition, react in an ice bath at room temperature for 5 hours; cool to room temperature, slowly add the reaction solution into dilute hydrochloric acid, collect the filter cake by filtration, and dry in vacuo to obtain 4.9 g of a light green solid. Yield 98%. This step is directly carried out to the next reaction without purification.

[0079] 2) Under an inert atmosphere, compound 2 (2.0g, 9.0mmol), n-butane bromide (3.1g, 22.5mmol), potassium carbonate (2.5g, 18.0mmol) and potassium iodide (0.30g, 1.80mmol) were dissolved in In 20mL N,N dimethylformamide, react at 90°C for 8 hours. Cool to room temperature, collect the filtrate by filtration, concentrate the filtrate and...

Embodiment 2

[0085] Synthesis of compound C8

[0086] The synthetic route is as follows:

[0087]

[0088] The preparation method of C8, its main steps are:

[0089] 1) The synthesis of compound 2 is the same as that of C4 in Example 1. This step is directly carried out to the next reaction without purification.

[0090] 2) Under an inert atmosphere, compound 2 (2.0g, 9.0mmol), n-octane bromide (4.35g, 22.5mmol), potassium carbonate (2.49g, 18.0mmol) and potassium iodide (0.30g, 1.80mmol) were dissolved in In 20mL N,N dimethylformamide, react at 90°C for 8 hours. Cool to room temperature, collect the filtrate by filtration, concentrate the filtrate and dilute with dichloromethane, then add water and dichloromethane for extraction and separation, collect the organic phase and dry it with anhydrous sodium sulfate. Use a silica gel column for separation, and the eluent is petroleum ether:dichloromethane=8:1. After drying in vacuum, 3.5 g of white powdery solid was obtained with a yiel...

Embodiment 3

[0096] Synthesis of Compound C10

[0097] The synthetic route is as follows:

[0098]

[0099] The preparation method of C10, its main steps are:

[0100] 1) The synthesis of compound 2 is the same as that of C4 in Example 1. This step is directly carried out to the next reaction without purification.

[0101] 2) Under an inert atmosphere, compound 2 (2.0g, 9.0mmol), n-bromodecane (4.98g, 22.5mmol), potassium carbonate (2.49g, 18.0mmol) and potassium iodide (0.30g, 1.80mmol) were dissolved in In 20mL N,N dimethylformamide, react at 90°C for 8 hours. Cool to room temperature, collect the filtrate by filtration, concentrate the filtrate and dilute with dichloromethane, then add water and dichloromethane for extraction and separation, collect the organic phase and dry it with anhydrous sodium sulfate. Use a silica gel column for separation, and the eluent is petroleum ether:dichloromethane=8:1. After vacuum drying, 3.62 g of a white powdery solid was obtained with a yield...

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PUM

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Abstract

The invention discloses a small molecular material with yellow mechanoluminescence of 10-membered fused ring benzothiadiazole as well as a preparation method and application of the small molecular material. The preparation method comprises the steps of 1) carrying out reduction reaction on a benzo [1, 2-b: 4, 5-b '] dithiophene-4, 8-diketone compound and sodium borohydride; 2) reacting the product in the step 1) with halogenated alkane; (3) reacting the product obtained in the step (2) with n-butyllithium and tributyltin chloride; (4) carrying out Stille coupling reaction; (5) carrying out a Cadogan reaction; and 6) reacting the product in the step 5) with halogenated alkane. The material prepared by the invention can be applied to a yellow mechanoluminescent material and a white mechanoluminescent material. The preparation method disclosed by the invention is relatively simple in process and relatively low in cost, and the prepared product has high fluorescence quantum yield in a solid state, has excellent yellow mechanoluminescence property, can generate mechanoluminescence white light emission with the CIE coordinate of (0.325, 0.346) after being doped with a blue mechanoluminescence material, and has good white light mechanoluminescence property.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to a benzothiadiazole-based ten-membered condensed-ring yellow mechanoluminescence material and its preparation method and application. Background technique [0002] Mechanoluminescence (ML) is an ancient and miraculous optical phenomenon, which was first recorded in Francis Bacon's "Advance of Learning" in 1605. Weak luminescence can be observed by scratching lumps of sugar in the dark . Generally speaking, mechanoluminescence refers to the phenomenon of luminescence under the action of mechanical force. The forms of mechanical force include but are not limited to grinding, scraping, shaking, blowing, pressing, etc. Mechanoluminescence can also be generated under the conditions of ultrasonic waves and infrared laser pulses. Mechanoluminescence is different from photoluminescence, electroluminescence, chemiluminescence, bioluminescence and other light emissio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/22C09K11/06
CPCC07D513/22C09K11/06C09K2211/1081Y02B20/00
Inventor 李倩倩常凯郭剑峰李振
Owner WUHAN UNIV
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