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Novel organic material capable of absorbing near-infrared light as well as preparation method and application thereof

A technology of near-infrared light and organic materials, applied in organic chemistry, chemical instruments and methods, and other chemical processes, can solve problems such as weak absorption effects, cumbersome and complex compound synthesis processes, and narrow absorption bands, and achieve enhanced charge push-pull effects , Low production cost, and the effect of promoting absorption and transformation

Inactive Publication Date: 2021-01-19
SOUTH CHINA UNIV OF TECH
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  • Application Information

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Problems solved by technology

However, compared with inorganic materials, near-infrared absorbing organic materials have been less studied, and most of them are organic polymers.
Chinese patent CN201510843714.3 prepared a small molecule organic semiconductor material with near-infrared absorption 2,2'-(2,8-bis(dialkylamino)-indeno[1,2-b]fluorene-6 ,12-diylidene)-dimalononitrile derivatives, the compound is based on 2,2'-(indeno[1,2-b]fluorene-6,12-diylidene)-dimalononitrile , with the amine-donating groups on the 2 and 8 positions as the auxochrome; the light absorption range of the compound in the solution state is concentrated in the ultraviolet and visible light regions (300-450nm), and it is only in the state of a thin film with a thickness of 30nm. Light in the infrared region has a weak absorption effect, which is not conducive to practical applications
Chinese patent CN201410853374.8 prepared a perylene imide derivative as a near-infrared light absorbing material, which can have a strong absorption effect on near-infrared light in the range of 650-700nm; The light absorption efficiency in the wavelength range is low, and the synthesis process of this compound is cumbersome and complicated, and the cycle is long, so it is not suitable for industrial application

Method used

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  • Novel organic material capable of absorbing near-infrared light as well as preparation method and application thereof
  • Novel organic material capable of absorbing near-infrared light as well as preparation method and application thereof
  • Novel organic material capable of absorbing near-infrared light as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Take 344.00 mg of 2-(2-(8-(4-(bis(4-methoxyphenyl)amino)phenyl)-6-hydroxy-2,3-dihydroxanth-4-yl) Vinyl)-1,3,3-trimethylindole salt (0.50mmol) and 125.27mg of 3,3-dimethyl-3-(2,4,5-trimethyl-3,6-di Oxycyclohexa-1,4-dien-1-yl)propionic acid (0.50mmol) was dissolved in a one-necked flask by adding 3mL of dichloromethane to obtain solution 1, which was cooled to 0°C. Dissolve 206.53mg of dicyclohexylcarbodiimide (1.00mmol) and 6.11mg of 4-dimethylaminopyridine (0.05mmol) in 3mL of dichloromethane to obtain solution 2, and inject solution 2 under nitrogen protection with a syringe Added dropwise to solution 1. The mixed solution was heated to room temperature and the reaction was stirred for 16h. Add water and dichloromethane for extraction, take the organic phase, dry with anhydrous sodium sulfate, and filter; remove the organic solvent by rotary evaporation, and the resulting solid is purified by silica gel chromatography (the eluent used is dichloromethane / methanol, V / V...

Embodiment 2

[0039] Take 1.511 g of 2-(2-(8-(4-(bis(4-methoxyphenyl)amino)phenyl)-6-hydroxy-2,3-dihydroxanth-4-yl) Vinyl)-1,3,3-trimethylindole salt (2.20mmol) and 660.28mg of 3,3-dimethyl-3-(2,4,5-trimethyl-3,6-di Oxycyclohexa-1,4-dien-1-yl)propionic acid (2.64mmol) was dissolved in a one-necked flask by adding 21.98mL of dichloromethane to obtain solution 1, which was cooled to 2°C. Dissolve 997.91mg of dicyclohexylcarbodiimide (4.84mmol) and 53.72mg of 4-dimethylaminopyridine (0.44mmol) in 24.18mL of dichloromethane to obtain solution 2, and use a syringe to place solution 2 under nitrogen protection Added dropwise to solution 1. The mixed solution was heated to room temperature and the reaction was stirred for 18h. Add water and dichloromethane for extraction, take the organic phase, dry with anhydrous sodium sulfate, and filter; remove the organic solvent by rotary evaporation, and the resulting solid is purified by silica gel chromatography (the eluent used is dichloromethane / metha...

Embodiment 3

[0042] Take 687.00 mg of 2-(2-(8-(4-(bis(4-methoxyphenyl)amino)phenyl)-6-hydroxy-2,3-dihydroxanth-4-yl) Vinyl)-1,3,3-trimethylindole salt (1.00mmol) and 275.19mg of 3,3-dimethyl-3-(2,4,5-trimethyl-3,6-di Oxycyclohexa-1,4-dien-1-yl)propionic acid (1.10mmol) was dissolved in a one-necked flask by adding 7.5mL of dichloromethane to obtain solution 1, which was cooled to 5°C. Dissolve 433.09mg of dicyclohexylcarbodiimide (2.10mmol) and 18.32mg of 4-dimethylaminopyridine (0.15mmol) in 8.4mL of dichloromethane to obtain solution 2, and use a syringe to protect solution 2 under nitrogen Add dropwise to a one-necked flask. The mixed solution was heated to room temperature and the reaction was stirred for 17h. Add water and dichloromethane for extraction, take the organic phase, dry with anhydrous sodium sulfate, and filter; remove the organic solvent by rotary evaporation, and the resulting solid is purified by silica gel chromatography (the eluent used is dichloromethane / methanol, ...

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Abstract

The invention relates to a novel organic material capable of absorbing near-infrared light as well as a preparation method and application of the novel organic material. The material is 2-(2-(8-(bis (4-methoxyphenyl) amino) phenyl)-6-((3, 3-dimethyl-3-(2, 4, 5-trimethyl-3, 6-dioxo cyclohex-1, 4-diene-1-yl) propionyl) oxy)-2, 3-dihydroxanthene-4-yl) vinyl)-1, 3, 3-trimethylindole salt. The materialis characterized in that an absorption peak is located in a near-infrared band (an absorption peak value is 685nm), and 650-800nm near-infrared light can be efficiently absorbed; the quinone propionate group serves as a strong fluorescence quenching group, so that more excited electrons return to the ground state in a non-radiative transition energy release mode, and the absorption and conversionefficiency of near-infrared light is promoted. The material can be applied to absorption and utilization of near-infrared light energy in the fields of energy, chemistry, electronics, environment andthe like.

Description

technical field [0001] The present invention relates to an organic material that absorbs near-infrared light, in particular to a novel organic material that can absorb near-infrared light and its preparation method and application. The organic material contains a conjugated double donor-π bridge-double acceptor The structure (2D-π-2A) belongs to the technical field of material synthesis and preparation. Background technique [0002] Materials that can absorb near-infrared light, also known as near-infrared light-absorbing materials, refer to a class of substances that can absorb near-infrared light. Materials that can absorb near-infrared light are currently widely used in many industrial fields, such as near-infrared light-absorbing pigments used in laser printers, charge-generating materials used in digital copy machines, and information storage materials used in optical discs, all of which are near-infrared light-absorbing pigments. Examples of applications of light-abso...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C09K3/00
CPCC07D405/06C09K3/00
Inventor 吴水珠王超黄靖曾钫
Owner SOUTH CHINA UNIV OF TECH
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