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Organic photochromic compound as well as preparation method and application thereof

A photochromic and compound technology, applied in organic chemistry, chemical instruments and methods, color-changing fluorescent materials, etc., can solve the problems of limited structure of organic photosensitive materials, achieve good photochromic effect, increase yield and purity, and simple preparation method Effect

Pending Publication Date: 2021-06-11
阜阳欣奕华制药科技有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The current structure of organic photosensitive materials is limited, and it is urgent to expand the types of organic photosensitive materials

Method used

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  • Organic photochromic compound as well as preparation method and application thereof
  • Organic photochromic compound as well as preparation method and application thereof
  • Organic photochromic compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0048] Preparation example 1 provides naphthol-1, and its preparation method is as follows:

[0049]

[0050] Add 0.1mol benzophenone-1 to 0.15mol dimethyl succinate, mix, add 0.2mol sodium tert-butoxide, carry out Stobbe condensation reaction, extract with ether to obtain intermediate a-1; add 0.5mol acetic anhydride Condensation and ring closure of intermediate a-1, rotary evaporation to remove excess acetic anhydride, recrystallization and purification with ethyl acetate, and drying to obtain intermediate b-1; dissolve intermediate b-1 in tetrahydrofuran, add 0.5mol of formazan Carry out methylation reaction between base magnesium chloride and intermediate b-1, and concentrate the solvent by rotary evaporation to obtain intermediate c-1; add toluene and catalytic amount of p-toluenesulfonic acid to carry out ring closure reaction, and obtain naphthol through toluene recrystallization -1.

preparation example 2

[0051] Preparation Example 2 provides naphthol-2, which is the same as Preparation Example 1, except that the benzophenone-1 is replaced by benzophenone-2, that is, the R=H is replaced by R=CH 3 .

preparation example 3

[0052] Preparation Example 3 provides naphthol-3, which is the same as Preparation Example 1, except that the benzophenone-1 is replaced by benzophenone-3, that is, the R=H is replaced by R=OCH 3 .

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Abstract

The invention relates to the field of organic photochromic materials, in particular to an organic photochromic compound and a preparation method and application thereof. The organic photochromic compound has a chemical structure as shown in formula 1 shown in the description, wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are the same or different and independently represent H, F, Cl, OH, C1-C4 alkyl, C1-C4 alkoxy and -NRnRm, and Rn and Rm independently represent C1-C3 alkyl. The organic photochromic compound provided by the invention is good in photochromic effect, can generate molecular structure change after absorbing ultraviolet rays, can be reversibly reduced into an initial molecular structure after the ultraviolet rays disappear, and is high in yield and purity.

Description

technical field [0001] The present application relates to the field of organic photochromic materials, in particular to an organic photochromic compound and its preparation method and application. Background technique [0002] Photochromic materials are roughly divided into two categories: inorganic photochromic materials and organic photochromic compounds. Inorganic photochromic materials generally refer to silver halide materials. When a certain amount of silver bromide is added to the glass lens, the silver bromide decomposes in the sunlight to produce a certain amount of halogen bromine to color the glass lens. When the sunlight disappears, the bromine halide can change back to silver halide to decolorize the glass lens. The color-changing principle of organic photochromic compounds is that the organic molecular structure of the material changes under sunlight, and the changed structure absorbs specific visible light in the visible light region, and people can observe ...

Claims

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Application Information

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IPC IPC(8): C07D311/96C09K9/02
CPCC07D311/96C09K9/02C09K2211/1088
Inventor 张浩
Owner 阜阳欣奕华制药科技有限公司