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Quinoline and spirooxazine photochromic compound and preparation method thereof

A technology of photochromism and spirooxazine, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of fatigue resistance, color and low application range, achieve bright color, low preparation cost, The effect of fast fading speed

Inactive Publication Date: 2012-05-30
TIANJIN FORESEEN TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The fatigue resistance, color and scope of application of the existing spirooxazine photochromic compounds are still low and need to be further improved, so it is necessary to develop new spirooxazine photochromic compounds

Method used

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  • Quinoline and spirooxazine photochromic compound and preparation method thereof
  • Quinoline and spirooxazine photochromic compound and preparation method thereof
  • Quinoline and spirooxazine photochromic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of 1,3,3-trimethyl-6'-morpholine-spiroindoline-2,3'-[3H]quinolino[2,1-b][1,4]oxazine photochromic compound.

[0032] The first step, the synthesis of 6-hydroxyquinoline

[0033] In a 100mL four-necked bottle, add 3.39g of ferric sulfate heptahydrate, 10.9g of p-aminophenol and 8.35g of p-nitrophenol, and then add 6.2g of boric acid dissolved in 29mL of glycerin to the four-necked bottle, stir and heat up To 70°C, stop heating, dropwise add 13mL of sulfuric acid with a mass percentage concentration of 98%, continue heating to a boiling state for 8 hours, and adjust the pH value of the system to 5 with a 30% NaOH aqueous solution with a mass percentage concentration after the reaction. , the product 6-hydroxyquinoline was obtained by suction filtration, and the productive rate was 61%;

[0034] The second step, the synthesis of 5-nitroso-6-hydroxyquinoline

[0035] Dissolve 2 g of 6-hydroxyquinoline prepared in the first step in 30 mL of NaOH aqueous soluti...

Embodiment 2

[0042] Preparation of 1,3,3-trimethyl-6'-piperidine-spiroindoline-2,3'-[3H]quinolino[2,1-b][1,4]oxazine photochromic compound.

[0043] The first step, with embodiment 1;

[0044] Second step, with embodiment 1;

[0045] The third step, the synthesis of 5-nitroso-6-hydroxyquinoline Cu complex

[0046] Dissolve 2mmol of CuCl with stirring 2 10ml of the aqueous solution was added dropwise to 30mL of tetrahydrofuran and water mixed solution having 5mmol of 5-nitroso-6-hydroxyquinoline prepared in the second step, the volume ratio of tetrahydrofuran to water was 1:1, and continued After stirring for 10 minutes, the product 5-nitroso-6-hydroxyquinoline Cu complex was obtained by suction filtration with a yield of 98%.

[0047] The fourth step, 1,3,3-trimethyl-6'-piperidine-spiroindoline-2,3'-[3H]quinolino[2,1-b][1,4]oxazine Synthesis of Photochromic Compounds

[0048]

[0049] In a 50mL three-necked flask, add 1mmol of the 5-nitroso-6-hydroxyquinoline Cu complex prepared in ...

Embodiment 3

[0051] Preparation of 1,3,3-trimethyl-6'-piperazine-spiroindoline-2,3'-[3H]quinolino[2,1-b][1,4]oxazine photochromic compound.

[0052] The first step, with embodiment 1;

[0053] Second step, with embodiment 1;

[0054] The 3rd step, with embodiment 1;

[0055] The fourth step, 1,3,3-trimethyl-6'-piperazine-spiroindoline-2,3'-[3H]quinolino[2,1-b][1,4]oxazine Synthesis of Photochromic Compounds

[0056]

[0057] In a 50mL four-neck flask, add 1mmol of 5-nitroso-6-hydroxyquinoline Zn complex prepared in the third step, then add 15mL of ethanol solvent, then stir and add 3.5mmol of piperazine, stir and heat Refluxed for 2 hours, then added dropwise 1.5mmol 1,3,3-trimethyl-2-methylene indoline and 15mL ethanol solvent, refluxed for 8 hours, followed by TLC monitoring, and separated by recrystallization after the reaction was terminated to obtain a solid The product, namely 1,3,3-trimethyl-6'-piperazine-spiroindoline-2,3'-[3H]quinolino[2,1-b][1,4]oxazine Photochromic comp...

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Abstract

The invention provides a quinoline bis-spirnaphthoxazine photochromic compound and a preparation method thereof, which relate to organic photochromic materials. The compound has a general chemical structural formula, wherein R1 is equal to CH3 in the formula. The preparation method of the quinoline bis-spirnaphthoxazine photochromic compound includes steps: (1), synthesis of 6-oxyquinoline; (2), synthesis of 5-nitroso-6-oxyquinoline; (3), synthesis of 5-nitroso-6-oxyquinoline metal complex; and (4), synthesis of the quinoline bis-spirnaphthoxazine photochromic compound. The preparation method of the compound is simple and is low in preparation cost, and the compound has better endurance and color, wider application range and higher productivity as compared with an existing spirooxazine photochromic compound.

Description

technical field [0001] The technical solution of the invention relates to an organic photochromic material, specifically a quinolino-spirooxazine photochromic compound and a preparation method thereof. Background technique [0002] Spirooxazine photochromic compounds can be used in many advanced technical fields such as optical information storage materials, anti-counterfeiting identification materials, light regulation of biomolecular activity, self-image photosensitive films and holographic materials. CN1629249 discloses 6'-heterocyclic substituted spirooxazine photochromic compounds and their preparation methods; "Synthesis, 2010, 15, 3418-3422" discloses the synthesis of substituted spirooxazines by the process of forming zinc complexes The method of photochromic compounds; JP07,132,667 and EP0316,980 also reported the relevant information of spirooxazine photochromic compounds. The fatigue resistance, color and scope of application of the existing spirooxazine photochr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/20C09K9/02
Inventor 孟继本庞美丽韩杰
Owner TIANJIN FORESEEN TECH
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