A kind of mechanochromic polymer material containing phenolphthalein derivative with fast self-recovery property and preparation method thereof

A polymer material and color-induced technology, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, etc.

Active Publication Date: 2021-04-20
NANJING INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current systems need to be restored by external stimulus conditions, such as light, pH, heat, etc.

Method used

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  • A kind of mechanochromic polymer material containing phenolphthalein derivative with fast self-recovery property and preparation method thereof
  • A kind of mechanochromic polymer material containing phenolphthalein derivative with fast self-recovery property and preparation method thereof
  • A kind of mechanochromic polymer material containing phenolphthalein derivative with fast self-recovery property and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of Mechanochromic Polymer Material 1

[0031] The preparation route is as follows:

[0032]

[0033] Concrete preparation steps are as follows:

[0034] a) Phenolphthalein (10mmol) was dissolved in 40mL of ethanol, ethanolamine (30mmol) was added to the above system, the system was refluxed and stirred for 24, and the solvent was distilled off under reduced pressure, and the crude product was separated and purified through silica gel chromatography (developing agent was dichloromethane / methanol=5 / 1) to obtain P-1. The yield was 90%. 1 H NMR (400MHz, CDCl 3 ):7.91(d,1H),7.58(m,1H),7.18(m,1H),7.03-7.08(m,5H),6.63(m,4H),5.30(s,2H),3.65(t, 2H), 3.61(s, 1H), 3.30(t, 2H).

[0035] b) Add P-1 (8mmol), anhydrous potassium carbonate (16mmol), bromoethanol (1.5mmol) into the solvent acetone. The reaction system was stirred overnight at 90° C. after freezing-vacuumizing-nitrogen three times. After the reaction was completed, the system was poured ...

Embodiment 2

[0037] Example 2: Preparation of Mechanochromic Polymer Material 2

[0038] The specific preparation steps are as follows: the same part (steps a and b) as in Example 1 will not be repeated, and the difference with Example 1 is that

[0039]Step c): P-2 (0.8 mmol) and di-tert-butyltin dilaurate (0.14 mmol) were dissolved in hexamethylene diisocyanate (1.4 mmol), and the system was stirred and reacted at 40°C. After 1 hour, dry polytetrahydrofuran (M n =2000g / mol, 2mmol) and anhydrous tetrahydrofuran (5mL) and continued stirring at 40°C for 2 hours. Then, the remaining hexamethylene diisocyanate (1.4 mmol) was slowly added into the solution and the stirring was continued at 40° C. for 3 hours, and finally the polymer was precipitated by methanol to obtain the lyrochromic polymer material 2 .

Embodiment 3

[0040] Example 3: Preparation of Mechanochromic Polymer Material 3

[0041] The preparation route is as follows:

[0042]

[0043] Concrete preparation steps are as follows: its identical part (step a) with embodiment 1 repeats no more, and the difference with embodiment 2 is in step:

[0044] b) Add P-1 (8mmol), anhydrous potassium carbonate (16mmol), bromoethanol (2.0mmol) into the solvent acetone. The reaction system was stirred overnight at 90° C. after freezing-vacuumizing-nitrogen three times. After the reaction was completed, the system was poured into water and extracted three times with chloroform. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product was separated and purified by silica gel column chromatography (gradient elution with n-hexane / ethyl acetate eluent from 1:0 to 1000:5) to obtain the target product P-3. The yield was 75%. 1 H NMR (400MHz, CDCl 3 ):7.91(1H,d),7.58(1...

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Abstract

The invention relates to a mechanochromic polymer material containing phenolphthalein derivatives with rapid self-recovery properties and a preparation method thereof. When the structure of the phenolphthalein derivatives in the polymer material is stressed, it will open and break to change the color of visible light. Since the ring-opening structure itself is a thermodynamically unstable state, it is easy to return to the closed-ring structure at room temperature, so the polymer material has a very fast self-recovery speed, and the color-changing group can be easily modified, so that it can be modified through various The introduction of this polymerization method into the polymer backbone will greatly promote its practical application in many fields such as biomimetic materials, optical storage, display, and mechanical sensing.

Description

technical field [0001] The invention relates to the field of organic intelligent materials, in particular to a mechanochromic polymer material containing phenolphthalein derivatives with rapid self-recovery properties and a preparation method thereof. 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 smart responsive fluorescent materials whose stimuli are pH, chemistry, electricity, and temperature, while the research on mechanochromic materials with force as the external stimuli is still in the development stage. It has many unique advantages in regulating the properties of materials: easy application, convenient regulation, simple operation, etc. Factors have great applica...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/73C08G18/66C08G18/48C08G18/38C08F220/18C08F222/22C09K9/02
CPCC08F220/18C08G18/3825C08G18/4854C08G18/6666C08G18/73C09K9/02C09K2211/14C08F222/22
Inventor 张娜汪太生
Owner NANJING INST OF TECH
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