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Furfural-based organic photochromic material and preparation method thereof

A photochromic material and organic technology, applied in the direction of color-changing fluorescent materials, organic chemical methods, organic chemistry, etc., can solve the problems of low yield, harsh reaction conditions, rare raw materials, etc., achieve high molar absorptivity, easy to obtain, High fatigue resistance effect

Active Publication Date: 2021-02-26
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the shortcomings of raw materials in the prior art, such as rare raw materials, harsh reaction conditions, low yield, and the need to use ultraviolet light to trigger photochemical reactions, the object of the present invention is to provide an organic photochromic material and a synthetic method thereof

Method used

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  • Furfural-based organic photochromic material and preparation method thereof
  • Furfural-based organic photochromic material and preparation method thereof
  • Furfural-based organic photochromic material and preparation method thereof

Examples

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Effect test

example 1

[0053] Compound I of the present invention has a molecular structure as follows:

[0054]

[0055] The preparation method of the compound of this example 1 may further comprise the steps:

[0056] Cyclo(ethylene)isopropyl malonate and furfural were sequentially added to H 2O middle. The heterogeneous mixture was heated to 75°C and stirred at this temperature for 2 hours, during which time a yellow precipitate formed. After the reaction (TLC) detection, hexane:ethyl acetate=3:1) the mixture was cooled to room temperature. The precipitated solid was collected by vacuum filtration and washed twice with cold water. The collected solid was dissolved in dichloromethane and washed with saturated NaHSO 3 、H 2 O, saturated NaHCO 3 and washed with brine. MgSO for organic layer 4 After drying and filtration, the solvent was removed by rotary evaporator to obtain a bright yellow powder. Its H NMR spectrum is shown in figure 1 .

example 2

[0058] Compound II, its molecular structure is as follows:

[0059]

[0060] The preparation method of the compound of this example 2 may further comprise the steps:

[0061] Mix 2-pyridinecarbaldehyde and ethylamine in a molar ratio of 1:2 and add to methanol, reflux and stir for 2h, then stir at room temperature for another 2h, then extract the yellow reaction mixture with ether three times. anhydrous MgSO 4 Dry, filter and evaporate to dryness, then add NaBH 4 After reduction, a yellow oily liquid was finally obtained. Its H NMR spectrum is shown in figure 2 .

example 3

[0063] Compound III, its molecular structure is as follows:

[0064]

[0065] The preparation method of the compound of this example 3 comprises the following steps:

[0066] In the two-necked flask, according to the molar ratio of compound I: pyridineethylamine = 1:1, sequentially add THF. The mixture was stirred for 10 minutes at 23°C, then cooled at 0°C for 20 minutes. After the reaction was complete, the mixture was filtered to collect solids. The solid was washed with cold ether and dried in vacuo to obtain a red solid. Its H NMR spectrum is shown in Figure 3-4 .

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Abstract

The invention discloses a furfural-based organic photochromic compound and a synthesis method thereof, the method comprises the following steps: reacting malonic acid cyclic (methylene) isopropyl ester with furfural to synthesize a compound I, adding a synthesized compound II, i.e. pyridine-2-ethylamine to generate a target compound III, and recrystallizing in a methanol solution to synthesize anisomer IV. A proper amount of alkali is added into the aqueous solution of the target compound III, and then converted into an isomer V; the organic photochromic compound with high yield and high content is obtained by using an organic solvent with lower toxicity and carrying out condensation reaction under certain conditions, and a catalyst is not needed, so that the production cost is effectively reduced, and the production efficiency is improved. The compound has wide application in the fields of molecular electron and information processing, light-operated catalysis, molecular materials, drug delivery, imaging and control of biological systems and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and mainly relates to a preparation method of a photochromic material. Background technique [0002] The ability of organic photochromic compounds to reversibly undergo spectral absorption, volume, and solubility changes is of particular interest in energy storage and chemical sensing applications, as well as in controlling the conformation and activity of biomolecules. [0003] Among organic photochromic materials, azobenzenes, spiropyrans, and dienes have attracted much attention due to their excellent properties and wide range of applications. Specifically, azobenzene has been widely used due to its volume change induced by trans isomerization to cis isomerization under irradiation. Likewise, changes in the spectral properties of spiropyrans and dienes on optical switches have also been exploited in many applications. Despite the ubiquity and wide-ranging applications of photochrom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C07D471/04C09K9/02
CPCC07D405/12C07D471/04C09K9/02C09K2211/1029C09K2211/1088C07B2200/13
Inventor 暴欣蔡佑德陈秀琴
Owner NANJING UNIV OF SCI & TECH
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