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Spiropyran photochromic compound and preparation method thereof

A compound and cyclization technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve problems such as high cost, unsuitable for large-area light-colored glass, and restrictions on commercial applications in the construction field

Inactive Publication Date: 2015-08-05
JIANGSU SHIKEXINCAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to its high cost and complex processing technology, it is not suitable for the production of large-area light-colored glass, which limits its commercial application in the construction field.

Method used

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  • Spiropyran photochromic compound and preparation method thereof
  • Spiropyran photochromic compound and preparation method thereof
  • Spiropyran photochromic compound and preparation method thereof

Examples

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Embodiment 1

[0038] Example 1 Preparation of 6,7-dimethoxy-3,3-bis(4-methoxyphenyl)-13-methyl-3,13-dihydrobenzo[h]indene[2,1- f] pyran-13-ol

[0039] 1. The preparation of compound s2, the reaction formula:

[0040]

[0041] In a 500mL three-necked flask, add 3,4-dimethoxybenzophenone (50.0g, 206mmol, 1.0eq), potassium tert-butoxide (46.3g, 413mmol, 2.0eq), tert-butanol (150mL), drop Dimethyl succinate (36.2g, 248mmol, 1.2eq) was added, and after the addition was completed, the reaction temperature was raised to 80°C for 20h. Add 100 mL of water, distill off tert-butanol, then add 100 mL of water, adjust the pH of the aqueous layer to acidic, extract with dichloromethane (80 mL×3), combine the organic layers, and anhydrous Na2 SO 4 After drying, the crude product was directly used for the next reaction after the solvent was distilled off under reduced pressure.

[0042] 2. The preparation of compound s3, the reaction formula:

[0043]

[0044] The crude product prepared in step 1...

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Abstract

The invention relates to a spiropyran photochromic compound shown as formula I. The preparation method includes: subjecting 3, 4-dimethoxy benzophenone and butyric acid dimethyl ester to condensation reaction under an alkaline condition to obtain a compound s2, conducting acetic anhydride reflux cyclization to obtain 4-acetoxy-6, 7-dimethoxy-1-phenyl-2-naphthoic acid methyl ester, then performing alkaline hydrolysis to obtain 4-hydroxy-6, 7-dimethoxy-1-phenyl-2-naphthoic acid s4, subjecting the compound s4 to cyclization under an acidic condition to obtain an intermediate 5-hydroxy-2, 3-dimethoxy-7H-benzo[c]fluorine-7-one, then carrying out reaction with a methyl Grignard reagent to obtain 2, 3-dimethoxy-7-methyl-7H-benzo[c]fluorene-5, 7-diol, and finally under the catalysis of p-toluenesulfonic acid, reacting 2, 3-dimethoxy-7-methyl-7H-benzo[c]fluorene-5, 7-diol with 1, 1-bis(4-methoxyphenyl)-2-propyne-1-ol to generate the compound shown as formula (I). The compound can change from colorless to green under ultraviolet irradiation, and can change from green to colorless after ultraviolet disappears.

Description

Technical field: [0001] The invention relates to a novel photochromic compound, in particular to a preparation method of a novel spiropyran photochromic compound. Background technique [0002] Photochromism refers to the change of the molecular structure of certain compounds under the action of light of a certain wavelength and intensity, resulting in a corresponding change in the color of the light absorption peak, and this change is generally reversible. It has been more than 100 years since human beings discovered the phenomenon of photochromism. The first successful commercial application began in the 1960s. Amistead and Stooky, two material scientists from Corning Studio in the United States, first discovered the reversible photochromic properties of silver halide glasses, and then people made contributions to its mechanism and applications. A lot of research and development of photochromic glasses. However, due to its high cost and complex processing technology, it i...

Claims

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Application Information

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IPC IPC(8): C07D311/78C09K9/02
CPCC07D311/78C09K9/02C09K2211/1088
Inventor 范为正纪立军王明华徐静涛张鹤军刘建中
Owner JIANGSU SHIKEXINCAI CO LTD
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