Forced-induced fluorescence color-changing compound and preparation method and application thereof

A compound and chromogenic technology, which is applied in the preparation methods of peptides, chemical instruments and methods, and addition of luminescent/fluorescent substances to achieve multiple social benefits, reduce carbon emissions, and save energy.

Active Publication Date: 2013-04-10
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the use of external force to change the properties of materials, especially the fluorescent properties of materials.

Method used

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  • Forced-induced fluorescence color-changing compound and preparation method and application thereof
  • Forced-induced fluorescence color-changing compound and preparation method and application thereof
  • Forced-induced fluorescence color-changing compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 - Mechanochromic Compounds Synthesis of (R 1 express R 2 express R 3 express )

[0028] step 1- Synthesis

[0029] Add 0.30g to a 25ml round bottom flask and 3ml of chloroform, stirred for 15min to fully dissolve it. Slowly add 0.5ml of trifluoroacetic acid solution dropwise and react at room temperature for 1h. After the reaction was completed, it was spin-dried, and 15 ml of ether was added into the round-bottomed flask under stirring conditions to obtain a white suspension. After filtering, the filter cake was washed with ether to obtain a white solid with a yield of 94%.

[0030] Step 2- Synthesis

[0031] Add 0.29g to a 50ml round bottom flask and 10ml chloroform. Add 0.5ml of triethylamine and 0.16g of 1-pyrenecarboxylic acid solid at -15°C, and then add 0.19g of condensing agent dicyclohexylcarboimide (DCC). After 48 hours of reaction, use dichloromethane / tetrahydrofuran (10:1) as eluent column separation to obtain pure product ...

Embodiment 2

[0033] Example 2 - Mechanochromic Compounds Synthesis of (R 1 express R 2 express R 3 express )

[0034] step 1- Synthesis

[0035] Add 0.60g to a 50ml round bottom flask and 3ml of chloroform, stirred for 15min to fully dissolve it. 1ml of trifluoroacetic acid solution was slowly added dropwise and reacted for 1h at room temperature. After the reaction was completed, it was spin-dried, and 25 ml of ether was added to the round-bottomed flask under stirring conditions to obtain a white suspension. After filtering, the filter cake was washed with ether to obtain a white solid with a yield of 95%.

[0036] Step 2- Synthesis

[0037] Add 0.55g to a 50ml round bottom flask and 20ml chloroform. 1ml of triethylamine and 0.32g of solid 2-anthracenecarboxylic acid were added at -15°C, and then 0.37g of condensing agent dicyclohexylcarboimide (DCC) was added. After 48 hours of reaction, use dichloromethane / tetrahydrofuran (10:1) as eluent column separation to ob...

Embodiment 3

[0039] Example 3 - Mechanochromic Compounds Synthesis of (R 1 express R 2 express R 3 Indicates -OC n h 2n+1 where n=1-18)

[0040] This embodiment adopts the similar synthesis steps as in Example 1, the difference is that the raw materials used in step 1 are (R 2 express R 3 Indicates -OC n h 2n+1 where n=1-18).

[0041] Compounds similar to pyrene as a modification group can also be synthesized by the same method, such as R 2 =-H,R 3 =-OC n h 2n+1 ;or R 2 =-CH 3 ,R 3 =-OC n h 2n+1 ;or R 3 =-OC n h 2n+1 ;or R 2 =-H,R 3 =-OC n h 2n+1 ;or R 2 =-CH 3 ,R 3 =-OC n h 2n+1 ;).

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Abstract

The invention provides forced-induced fluorescence color-changing compounds and a preparation method and application thereof. The structural formulas of the compounds are shown by a formula (I) and a formula (II). Under the effect of external force, the fluorescence color can be changed. After the compounds are simply treated by using solvent and the like, the original fluorescence color can be restored. On the basis of the compounds, rewritable fluorescence color-changing paper can be prepared by using a simple technology.

Description

technical field [0001] The invention belongs to the field of organic intelligent materials, and specifically provides a preparation method and application of a mechanofluorochromic compound. Background technique [0002] The development and wide application of smart materials have made people's demand for functional organic materials increasingly urgent. Various performance indicators of this type of material can be effectively regulated by using external stimuli, so that various functions can be realized. There have been many reports on the regulation of the properties of materials by means of pH, external ions, light and heat. As a widely existing external stimulus, external force (pressure, friction, etc.) has many unique advantages in regulating the properties of materials: easy to apply, convenient to control, simple to operate, etc. However, there are few reports on the use of external force to change the properties of materials, especially the fluorescent properties...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/062C07K5/065C07K1/06C09K9/02D21H21/30
Inventor 滕明俊贾欣茹
Owner PEKING UNIV
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