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Novel dicarboxyl spiropyrane derivative and preparation method thereof

A technology of spiropyran derivatives and dicarboxylic groups, which is applied in the field of novel dicarboxyspiropyran derivatives and its preparation, can solve the problems of thermal stability, poor fatigue resistance, instability of cyanine body at the ring-opening part, and limited application fields etc. to achieve the effects of easy reaction conditions, excellent photochromic properties, and a wide range of substrates

Active Publication Date: 2019-12-20
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the ring-opening cyanine body (SP) of spiropyran is very unstable, and it is easy to fade and return to a colorless closed-ring body, and there are problems such as thermal stability and fatigue resistance, which limit its application field.

Method used

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  • Novel dicarboxyl spiropyrane derivative and preparation method thereof
  • Novel dicarboxyl spiropyrane derivative and preparation method thereof
  • Novel dicarboxyl spiropyrane derivative and preparation method thereof

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Embodiment 1

[0039] as attached Figure 2-5 As shown, the present invention proposes a novel biscarboxy spiropyran derivative and a preparation method thereof, specifically comprising the following steps:

[0040] S1, synthesis of 3,5-dicarboxyphenylhydrazine hydrochloride;

[0041] Add 8.0g of aminoisophthalic acid and 50mL of water into a 150mL round bottom flask, add 10mL of concentrated hydrochloric acid to dissolve it, keep the temperature below 5°C in an ice-salt bath, stir the solution into a slurry, and slowly add 3.0 6mL aqueous solution of sodium nitrite, stop adding until the starch potassium iodide test paper turns slightly blue, and keep magnetic stirring throughout the whole process to form reaction solution A; weigh 18.0g sodium sulfite and add it to a 300mL round-bottomed flask, then add 65mL water and stir to dissolve, dissolve and pour into Slowly add the above reaction solution A dropwise and keep stirring. After stirring for 1 hour, add 22mL of concentrated hydrochlori...

Embodiment 2

[0049] as attached Figure 2-5 As shown, the present invention proposes a novel biscarboxy spiropyran derivative and a preparation method thereof, specifically comprising the following steps:

[0050] S1, synthesis of 3,5-dicarboxyphenylhydrazine hydrochloride;

[0051] Add 9.0g of aminoisophthalic acid and 50mL of water into a 150mL round bottom flask, add 13mL of concentrated hydrochloric acid to dissolve it, keep the temperature below 5°C in an ice-salt water bath, stir the solution into a slurry, and slowly add 3.5 6mL of aqueous solution of sodium nitrite, stop adding until the starch potassium iodide test paper turns slightly blue, and keep magnetic stirring throughout the whole process to form reaction solution A; weigh 18.9g of sodium sulfite and add it to a 300mL round bottom flask, then add 65mL of water and stir to dissolve, dissolve and pour into Slowly add the above-mentioned reaction solution A and keep stirring. After stirring for 1.5 hours, add 25mL of concent...

Embodiment 3

[0062] as attached Figure 2-5 As shown, the present invention proposes a novel biscarboxy spiropyran derivative and a preparation method thereof, specifically comprising the following steps:

[0063] S1, synthesis of 3,5-dicarboxyphenylhydrazine hydrochloride;

[0064] Add 10.0g of aminoisophthalic acid and 50mL of water into a 150mL round bottom flask, add 15mL of concentrated hydrochloric acid to dissolve it, keep the temperature below 5°C in an ice-salt water bath, stir the solution into a slurry, and slowly add 4.0 6mL of aqueous solution of sodium nitrite, stop adding until the starch potassium iodide test paper turns slightly blue, and keep magnetic stirring throughout the whole process to form reaction solution A; weigh 20.0g of sodium sulfite and add it to a 300mL round bottom flask, then add 65mL of water and stir to dissolve, dissolve and pour into Slowly add the above-mentioned reaction solution A and keep stirring. After stirring for 2 hours, add 30mL of concentr...

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Abstract

The invention discloses a novel dicarboxyl spiropyrane derivative and a preparation method thereof in the technical field of organic synthesis. The preparation method comprises the following steps: S1, synthesizing 3,5-dicarboxyl phenylhydrazine hydrochloride; S2, synthesizing 2,3,3-trimethyl-3H-indole-4,6-dioctyl phthalate; S3, synthesizing 1,3,3-trimethyl-2-methylene-4,6-dicarboxyl-3H-indole; and S4, synthesizing 6-methyl-8-aldehyde-1',3',3'-trimethyl spiro[benzopyran-2,2'-indole]-4',6'-dioctyl phthalate. By introducing two carboxyl groups to an indoline part of spiropyrane, and introducingaldehyde to the site 8 on a pyranoid ring, the spiropyrane both has an electron absorption function and can form a hydrogen bond stable open-loop cyanine (SP) together with oxygen, has excellent chemical stability and photochromic performance, in addition, has a very good metal coordination capability, and can be matched with most metals without affecting open-loop capabilities of the metals.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a novel dicarboxyspiropyran derivative and a preparation method thereof. Background technique [0002] Since fiesher and Hirsherg discovered the photochromic phenomenon of spiropyran in 1952, the research on spiropyran has attracted extensive attention of scientists all over the world, and it has become a class of organic photochromic compounds with the most extensive and deepest research. The photochromic mechanism of spiropyran is mainly based on the heterocleavage of the bond. Under the irradiation of ultraviolet light, the C-O bond of the spiropyran closed ring (MC) undergoes heterocleavage, isomerization or rearrangement of the electronic configuration, and becomes aromatic. Coplanar split cyanine body (SP). [0003] Due to its good photochromic properties, spiropyran has become a hot spot in the design of functional devices that mimic integrated logic gates and c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K9/02G01N21/64
CPCC07D491/107C09K9/02C09K2211/1029C09K2211/1088G01N21/643
Inventor 庾慧陈云宋蓉郭天琪吴嘉媚
Owner HUNAN UNIV
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