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Indeno-condensed naphtho-spirooxazine photochromic compound and preparation method thereof

A naphthospiroxazine, photochromic technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of low photoreaction conversion efficiency, and achieve rapid photoresponse, fast fading, and fatigue resistance. good effect

Active Publication Date: 2020-07-24
NANKAI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of diarylethene photochromic materials is that the photoreaction conversion efficiency is low, generally not more than 50%.
The introduction of indene fused ring improves the color rate and fading rate of naphthopyran compounds, but due to the existence of the TT-type isomer of the color changer, the color fading rate still needs to be further improved

Method used

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  • Indeno-condensed naphtho-spirooxazine photochromic compound and preparation method thereof
  • Indeno-condensed naphtho-spirooxazine photochromic compound and preparation method thereof
  • Indeno-condensed naphtho-spirooxazine photochromic compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of embodiment 1 photochromic compound Ia

[0034] The first step: Synthesis of 7,7-dimethyl-5-nitroso-7H-benzo[c]fluoren-6-ol

[0035]

[0036] Add 7,7-dihydrocarbyl-7H-benzo[c]fluoren-6-ol (0.41g, 1.6mmol), 20mL of acetonitrile, 20mL of water and 3mL of sodium hydroxide (2%) into a round-bottomed flask, ice-bathed , stir. A small amount of sodium nitrite (0.11 g, 1.65 mmol) was added as a solid, and the reaction was stirred for 1 hour at 0-5°C. 0.38 mL of dilute sulfuric acid solution (5.6 M) was added to the reaction liquid, and the reaction was continued for 1 hour. Suction filtration, the filter cake was washed twice with a small amount of water, and dried. The crude product was purified by silica gel column chromatography using a mixture of petroleum ether: ethyl acetate = 30:1 by volume as the eluent to obtain 0.36 g of an orange-red solid product with a yield of 78%.

[0037] The characterization data of 7,7-dihydrocarbyl-7H-benzo[c]fluoren...

Embodiment 2

[0044] The preparation of embodiment 2 photochromic compound Ib, reaction formula is as follows:

[0045]

[0046] Add 0.29 g (1.00 mmol) of 7,7-dimethyl-5-nitroso-7H-benzo[c]fluoren-6-ol and 30 mL of ethanol into the reaction flask, stir to dissolve, and heat to 90°C. N 2 For protection, slowly dropwise add 5-mL ethanol solution containing 0.25 g (1.20 mmol) of 5-chloro-1,3,3-trimethyl-2-methyleneindoline, and react under reflux for 24 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using a mixture of petroleum ether: ethyl acetate = 200:1 by volume as the eluent to obtain 80 mg of a brown oily product with a yield of 17%.

[0047] The proton nuclear magnetic resonance spectrum characterization data of 1b is: 1 H NMR (400MHz, CDCl 3 )δ8.71(d, J=8.0Hz, 2H), 8.32(d, J=8.0Hz, 1H), 7.82(s, 1H), 7.64–7.60(m, 1H), 7.57–7.53(m, 1H ),7.42...

Embodiment 3

[0049] The preparation of embodiment 3 photochromic compound Ic, reaction formula is as follows:

[0050]

[0051] Add 0.15 g (0.52 mmol) of 7,7-dimethyl-5-nitroso-7H-benzo[c]fluoren-6-ol and 20 mL of ethanol obtained in the previous step into the reaction flask, stir to dissolve, and heat to 90 ℃. N 2 For protection, a 5 mL ethanol solution containing 1,3,3-trimethyl-2-methyleneindoline 111 mg (0.62 mmol) was slowly added dropwise, and the reaction was refluxed for 24 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using a mixture of petroleum ether: ethyl acetate = 200:1 by volume as the eluent to obtain 70 mg of a brown oily product with a yield of 30%.

[0052] The H NMR spectrum characterization data of Ic are: 1 H NMR (400MHz, CDCl 3 )δ8.74(d, J=8.0Hz, 1H), 8.70(d, J=8.0Hz, 1H), 8.31(d, J=8.0Hz, 1H), 7.84(s, 1H), 7.63–7.59( ...

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PUM

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Abstract

The invention belongs to the field of organic photochromic materials, and particularly discloses an indeno-condensed naphtho-spirooxazine photochromic compound, which has a structure shown as a formula I. In the formula I, R1 is hydrogen, straight-chain or branched-chain alkyl, straight-chain or branched-chain alkoxy, halogen or nitro; r2 and R3 are straight-chain or branched-chain alkyl with thecarbon atom number being 1-6. The invention further provides a synthesis method of the compound. The indeno-condensed naphtho-spirooxazine photochromic compound disclosed by the invention has the characteristics of fast photoresponse, fast fading, no ground color, good fatigue resistance and the like.

Description

technical field [0001] The invention relates to the field of organic photochromic materials, in particular to an indene-condensed naphthospirooxazine photochromic compound and a preparation method thereof. Background technique [0002] Photochromism means that the molecular structure of certain compounds will change under the irradiation of light of a certain wavelength, resulting in obvious changes in their absorption spectrum, accompanied by color changes. Under the irradiation of another wavelength of light or heat, it will return to its original state. Photochromism is a reversible chemical change process. In recent years, photochromic materials have been widely used in optical information storage, optical switches, light regulation, optical devices, color-changing glasses, and color-changing clothing. [0003] Organic photochromic compounds mainly include diarylethenes, azobenzenes, benzene / naphthopyrans, and spirooxazines. Among them, the color-changing mechanism of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10C09K9/02
CPCC07D498/10C09K9/02C09K2211/1048
Inventor 韩杰孙娟娟刘双燕席志强孟继本刘宗
Owner NANKAI UNIV
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