Covalent macrocyclic polymer based on pillar [5] arene as well as preparation and application of covalent macrocyclic polymer

A polymer and covalent technology, used in the preparation of hydrazones, organic chemistry, chemical instruments and methods, etc., can solve the problems of limited control efficiency and complex chemical synthesis process, and achieve improved fatigue resistance, wide application prospects, thermal stability. Excellent effect

Active Publication Date: 2021-06-22
TIANJIN UVOS TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, molecular structure modification is mainly used to control the fading rate. This method involves a complex chemical synthesis process and the control efficiency is limited. The use of porous organic polymers to control the fading rate has not been reported.

Method used

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  • Covalent macrocyclic polymer based on pillar [5] arene as well as preparation and application of covalent macrocyclic polymer
  • Covalent macrocyclic polymer based on pillar [5] arene as well as preparation and application of covalent macrocyclic polymer
  • Covalent macrocyclic polymer based on pillar [5] arene as well as preparation and application of covalent macrocyclic polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 Synthesis of covalent macrocyclic polymer I based on pillar [5] arene

[0052] The first step: synthesis of intermediate A2

[0053] In a 250mL round bottom flask, add magneton, compound A1 (1.5g, 1.5mmol), 4-ethoxycarbonylphenylboronic acid (1.5g, 7.5mmol), sodium carbonate (795mg, 7.5mmol), tetrakis (triphenylphosphine ) palladium (451mg, 0.39mmol), under nitrogen protection, a mixed solvent of tetrahydrofuran and water (80mL, THF / H2O=5 / 1) was added, and stirred at 80°C for 72h. After cooling to room temperature, the reaction solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off under reduced pressure and separated by silica gel column chromatography to obtain intermediate A2 (petroleum ether: ethyl acetate = 10:1). White solid, 1.1g, melting point 145.8-147.1°C, yield 74%.

[0054] Proton NMR spectrum data of A2: 1 H NMR (400MHz, CDCl 3 )δ7.89(d, J=8.3Hz, 4H), 7.04d, J=8.1Hz, 4H),...

Embodiment 2

[0063] Example 2 Naphthopyran Photochromic Compound II (n=4, R=CH 3 O) Synthesis

[0064] The first step: Intermediate B2 (n=4, R=CH 3 O) Synthesis

[0065] Into a 250mL round bottom bottle, add magneton, B1 (3.2g, 14mmol), sodium iodide (2.65g, 18mmol), potassium carbonate (3.87g, 28mmol) and DMF (100mL), and stir at 100°C for 30 minutes. A solution of 5-bromovaleronitrile (2.87 g, 18 mmol) in DMF (30 mL) was added dropwise to the mixture and stirred for 3 h. After cooling to room temperature, the reaction mixture was added to ice water, extracted with dichloromethane, and the organic phases were combined and dried over anhydrous magnesium sulfate. Filtration, concentration, and recrystallization gave Intermediate B2. Colorless solid, 3.26g, melting point 115.3-116.1°C, yield 75%.

[0066] B2 (n=4, R=CH 3 O) proton nuclear magnetic resonance spectrum data: 1 H NMR (400MHz, CDCl 3 )δ7.78(dd, J=8.7, 1.9Hz, 4H), 6.95(t, J=8.7Hz, 4H), 4.09(t, J=5.6Hz, 2H), 3.88(s, 3H), 2....

Embodiment 3

[0076] Example 3 Preparation of photochromic polymethyl methacrylate composite film A

[0077] Add a magneton into a 50mL round bottom bottle, and accurately weigh the naphthopyran photochromic compound II (n=4, R=CH 3 O) (10 mg) and polymethyl methacrylate PMMA (1 g), added chloroform (15 mL), stirred at room temperature for 2 h, then heated to 60 ° C to dissolve PMMA, forming a transparent solution. The solution was poured into a watch glass (φ6cm×1.5cm), and placed in the dark at room temperature for 24 hours to obtain a composite film A.

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Abstract

The invention provides a covalent macrocyclic polymer based on pillar [5] arene as well as a preparation method and application thereof. The structure of the covalent macrocyclic polymer is shown as a formula I, the covalent macrocyclic polymer not only has a microporous structure formed by crosslinking monomers, but also has a cavity structure of pillararene, is a novel multistage microporous structure material, is large in specific surface area and excellent in thermal stability, can remarkably improve the color fading rate of a photochromic material, and is a new strategy for regulating and controlling the color fading rate.

Description

technical field [0001] The invention relates to the field of porous organic polymer materials, in particular to a preparation method of a covalent macrocyclic polymer material constructed with pillar [5] arene as a structural unit and its application in regulating the fading rate of organic photochromic materials. Background technique [0002] Pillar arene is the fifth generation supramolecular main compound after crown ether, cyclodextrin, calixarene and cucurbituril. This kind of compound is composed of 1,4-dimethoxybenzene unit through 2,5 para-methylene Bridged into a ring molecule, with a highly symmetrical columnar structure. The columnar cavity structure of pillararene is an electron-rich system, which can selectively complex neutral molecules and positively charged groups or ions. It has unique host-guest properties and highly adjustable functional characteristics. Adsorption and separation science, phase transfer catalysis, artificial membrane channels, electrochem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/86C07C249/16C09K9/02
CPCC07C251/86C09K9/02C07C2603/92C09K2211/1088Y02P20/55
Inventor 韩杰刘宗刘双燕张丽鑫
Owner TIANJIN UVOS TECH CO LTD
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