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Spirooxazine photochromic compound changing from colorless to blue as well as preparation method and application of spirooxazine photochromic compound

A photochromic and compound technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve problems such as instability of the open ring state

Pending Publication Date: 2020-10-23
畅的新材料科技(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, under the irradiation of ultraviolet light, spirooxazine photochromic materials, the colorless closed-ring state is stable, while the colored open-ring state is unstable.

Method used

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  • Spirooxazine photochromic compound changing from colorless to blue as well as preparation method and application of spirooxazine photochromic compound
  • Spirooxazine photochromic compound changing from colorless to blue as well as preparation method and application of spirooxazine photochromic compound
  • Spirooxazine photochromic compound changing from colorless to blue as well as preparation method and application of spirooxazine photochromic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Synthesis of a colorless to blue spirooxazine photochromic compound Ia:

[0036] The first step: the synthesis of M2a, the reaction formula is as follows:

[0037]

[0038] In a 250ml four-neck flask, add fluorenone (9.003g, 0.050mol), then add 100ml of glacial acetic acid solvent, magnetically stir, heat to 30℃, dissolve completely, then slowly add NBS (10.680g, 0.060 mol). After the addition, the reaction was continued at 30°C for 3h (TCL monitoring). After the reaction, the reaction solution was poured into a large amount of water. The product was separated out, filtered with suction, washed with water, and recrystallized with petroleum ether / ethyl acetate. Yield: 76%.

[0039] Step 2: Synthesis of M3a, the reaction formula is as follows:

[0040]

[0041] In a 100ml four-necked flask, add 80ml of deionized water, under magnetic stirring, add NaOH (1.200g, 0.030mol), heat to 100℃ to dissolve completely, then slowly add M2a (5.159g, 0.020mol), the addition is comp...

Embodiment 2

[0052] Example 2 Synthesis of a colorless to blue spirooxazine photochromic compound Ib:

[0053] The first step: the synthesis of M2b, the reaction formula is as follows:

[0054]

[0055] In a 100ml four-neck flask, add fluorenone (9.003g, 0.050mol), then add 100ml of glacial acetic acid solvent, magnetically stir, constant temperature at 25℃, dissolve completely, then slowly add NBS (8.890g, 0.050 mol). After the addition is complete, continue to stir the reaction at 25°C for 4h (TCL monitoring). After the reaction is complete, pour the reaction solution into a large amount of water. The product is separated out, filtered with suction, washed with water, and recrystallized with petroleum ether / ethyl acetate. Yield: 55%.

[0056] Step 2: Synthesis of M3b, the reaction formula is as follows:

[0057]

[0058] In a 100ml four-neck flask, add 80ml deionized water and 12ml ethanol. Under magnetic stirring, add NaOH (1.160g, 0.029mol), heat to 90℃ to dissolve completely, then slowly add...

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PUM

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Abstract

The invention discloses a spirooxazine photochromic compound changing from colorless to blue as well as a preparation method and application of the spirooxazine photochromic compound, and belongs to the technical field of organic functional materials. The objective of the invention is to develop and meet aesthetic needs of customers. The invention discloses a photochromic compound with high outdoor stability and a formula of a coating thereof. The spirooxazine photochromic compound changing from colorless to blue prepared by the invention has the advantages of high photoresponse speed, high fading speed, stable performance in a closed-loop state in outdoor use, low-price and easily available synthetic raw materials and high operability of a synthetic process, and meets the market aestheticrequirements.

Description

Technical field [0001] The invention relates to a spirooxazine photochromic compound that changes colorless to blue, and a preparation method and application thereof, belonging to the technical field of organic functional materials. Background technique [0002] Photochromic materials can absorb the energy of sunlight / ultraviolet rays after being irradiated by sunlight / ultraviolet rays. The molecular structure changes from a closed-loop state to an open-loop state, resulting in a change in its absorption wavelength in the visible light region, resulting in color changes; / Under ultraviolet energy, the molecular structure returns to the original molecular structure, the color of the colored state fades, and it returns to the original color, that is, the colorless state. [0003] Spirooxazine-based photochromic materials have received widespread attention due to their fast discoloration speed and fast discoloration speed. However, the colorless closed-loop state of the spirooxazine...

Claims

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Application Information

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IPC IPC(8): C07D498/10C09K9/02C09D5/29C09D133/04
CPCC07D498/10C09K9/02C09D5/29C09D133/04C09K2211/1048C08K5/00C08K5/353
Inventor 宋亚李曼郑文李方园
Owner 畅的新材料科技(上海)有限公司
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