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An organic material capable of absorbing near-infrared light and its preparation method and application

A technology of organic materials and near-infrared light, applied in organic chemistry, optical filters, etc., can solve the problems of low absorption efficiency of near-infrared light, unfavorable applications, and limited use range, etc., and achieve good near-infrared light absorption performance, charge push-pull Effect enhancement, effect that promotes rapid dissipation

Active Publication Date: 2022-03-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN109422460A has prepared a kind of glass for near-infrared absorption filter. Although the transmission characteristics of visible light are good and have certain grinding performance, this is a near-infrared filter based on glass material, so the absorption wavelength of the material is short. , narrow range, low strength, poor elasticity and other shortcomings, which seriously limit its scope of use
Chinese patent CN103270019A prepared a compound based on diimine and a near-infrared absorption filter using the compound. Although the absorption wavelength range of this material can reach 750nm-1000nm, the structure of the material is complex, and these defects also limit industrialization of this material
Chinese patent CN112239463A prepared a kind of organic small molecule material 2-(2-(8-(4-(bis(4-methoxyphenyl)amino)phenyl)-6-((3, 3-Dimethyl-3-(2,4,5-trimethyl-3,6-dioxocyclohex-1,4-dien-1-yl)propionyl)oxy)-2,3 -Dihydroxanthene-4-yl)vinyl]-1,3,3-trimethylindole salt, the material introduces indole as an electron-withdrawing group and quinone propionate group as a strong fluorescence quencher Although the material can absorb near-infrared light in the wavelength range of 650nm-800nm, the absorption intensity of the material is only 0.01-0.11, which leads to low absorption efficiency of near-infrared light of the material, which is not conducive to the near-infrared light absorption in the near-infrared light. Applications of Infrared Filters

Method used

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  • An organic material capable of absorbing near-infrared light and its preparation method and application
  • An organic material capable of absorbing near-infrared light and its preparation method and application
  • An organic material capable of absorbing near-infrared light and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation steps of the organic material that can absorb near-infrared light in this example are as follows:

[0031] Take 319.12 mg of 6-(bis(4-(pentyloxy)phenyl)amino)-1-ethyl-2-methylquinoline salt (0.50 mmol) containing iodine counterion and 114.04 mg of 6-hydroxy-2 , 3-Dihydroxanthene-4-carbaldehyde (0.50 mmol) was added to a one-necked flask, and 5 mL of n-butanol was added and mixed evenly. The mixed solution was heated to 118°C, stirred and refluxed for 10h. After the reaction was finished, it was lowered to room temperature, and the organic solvent was removed by rotary evaporation, and the resulting solid was purified by silica gel column chromatography (the eluent used was dichloromethane / ethyl acetate, V / V=20:1) to obtain the product 6- (Bis(4-(pentyloxy)phenyl)amino)-1-ethyl-2-(2-(6-hydroxy-2,3-dihydroxanthene)vinyl)quinoline salt.

[0032] The resulting product was characterized by proton nuclear magnetic resonance spectroscopy: 1 H NMR (600MHz, CD...

Embodiment 2

[0036] The preparation steps of the organic material that can absorb near-infrared light in this example are as follows:

[0037] Take 1.276 g of 6-(bis(4-(pentyloxy)phenyl)amino)-1-ethyl-2-methylquinolinate (2.00 mmol) containing iodine counterion and 547.39 mg of 6-hydroxy - 2,3-Dihydroxanthene-4-carbaldehyde (2.40 mmol) was added to a one-necked flask, and 24 mL of n-butanol was added and mixed evenly. The mixed solution was heated to 122°C, stirred and refluxed for 12h. After the reaction was finished, it was lowered to room temperature, and the organic solvent was removed by rotary evaporation, and the resulting solid was purified by silica gel column chromatography (the eluent used was dichloromethane / ethyl acetate, V / V=20:1) to obtain the product 6- (Bis(4-(pentyloxy)phenyl)amino)-1-ethyl-2-(2-(6-hydroxy-2,3-dihydroxanthene)vinyl)quinoline salt.

[0038] The final product characterization of Example 2 is the same as the result in Example 1.

Embodiment 3

[0040] The preparation steps of the organic material that can absorb near-infrared light in this example are as follows:

[0041] Take 638.24 mg of 6-(bis(4-(pentyloxy)phenyl)amino)-1-ethyl-2-methylquinolinate (1.00 mmol) containing iodine counterion and 250.89 mg of 6-hydroxy -2,3-Dihydroxanthene-4-carbaldehyde (1.10 mmol) was added to a one-necked flask, and 11 mL of n-butanol was added and mixed evenly. The mixed solution was heated to 120°C, stirred and refluxed for 11h. After the reaction was finished, it was lowered to room temperature, and the organic solvent was removed by rotary evaporation, and the resulting solid was purified by silica gel column chromatography (the eluent used was dichloromethane / ethyl acetate, V / V=20:1) to obtain the product 6- (Bis(4-(pentyloxy)phenyl)amino)-1-ethyl-2-(2-(6-hydroxy-2,3-dihydroxanthene)vinyl)quinoline salt.

[0042] The final product characterization of Example 3 is the same as the result in Example 1.

[0043] The 6-(bis(4-(pe...

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Abstract

The invention discloses an organic material capable of absorbing near-infrared light, a preparation method and application thereof. Such organic materials include 6-(bis(4-(pentyloxy)phenyl)amino)-1-ethyl-2-(2-(6-hydroxy-2,3-dihydroxanthene)vinyl ) quinoline salt, whose structure includes xanthene, quinoline salt group and diphenylamine group containing two pentyloxy groups, which can produce relatively high-intensity absorption for near-infrared light in the 620nm-800nm ​​band. The organic material is easy and quick to synthesize, has low preparation cost, can be applied to near-infrared absorption filters, and has good industrialization prospects.

Description

technical field [0001] The invention relates to an organic material capable of absorbing near-infrared light and its preparation method and application, in particular to a new type of organic material that can be used for near-infrared absorption filters and its preparation method and application, belonging to the synthesis and preparation of organic materials technology field. Background technique [0002] Low-light night vision technology is a photoelectric technology that converts low-brightness light that cannot be perceived by the human eye into a high-brightness image visible to the human eye through photoelectric imaging devices. It has a wide range of applications in aviation and military fields. The most commonly used low-light night vision device is the third-generation night vision goggle, which uses highly sensitive GaAs as the photocathode image intensifier tube, and the maximum spectral response range is 625nm-930nm. However, this type of night vision device i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06G02B5/20
CPCC07D405/06G02B5/20
Inventor 吴水珠马韵清欧阳娟孙立和曾钫
Owner SOUTH CHINA UNIV OF TECH
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