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

CN112239463AInactive Publication Date: 2021-01-19SOUTH CHINA UNIV OF TECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2021-01-19
Estimated Expiration
Not applicable · inactive patent

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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.
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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...

Examples

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, ...