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A kind of efficient organic near-infrared fluorescent material and its preparation and application

A fluorescent material and near-infrared technology, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problem of low photoluminescence efficiency, and achieve the effect of strong penetrating ability, avoiding autofluorescence and low excitation energy.

Active Publication Date: 2021-11-12
HUZHOU TEACHERS COLLEGE
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Problems solved by technology

[0005] The purpose of the present invention is to provide a high-efficiency organic near-infrared fluorescent material and its preparation and use, which solves the problem of low photoluminescence efficiency of existing near-infrared fluorescent materials, not only can have the largest fluorescence emission peak at 701nm, but also have the absolute quantum Efficiency up to 48.7%

Method used

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  • A kind of efficient organic near-infrared fluorescent material and its preparation and application
  • A kind of efficient organic near-infrared fluorescent material and its preparation and application
  • A kind of efficient organic near-infrared fluorescent material and its preparation and application

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preparation example Construction

[0034] The preparation method of the above-mentioned high-efficiency organic near-infrared fluorescent material includes:

[0035] (S1) Synthesis of Intermediate Benzothiadiazole Derivatives (Ⅱ)

[0036] The synthetic route of this benzothiadiazole derivative (II) is as follows:

[0037]

[0038] Weigh (4-(2'-(4"-methoxyphenyl)amino)phenyl)boronic acid, 7-bromo-4-formylbenzothiadiazole, tetrakis(triphenylphosphine)palladium dissolved in In the mixed solution of toluene / tetrahydrofuran, add an inorganic strong alkali solution (K 2 CO 3 solution). Among them, (4-(2'-(4″-methoxyphenyl)amino)phenyl)boronic acid: 7-bromo-4-formylbenzothiadiazole: tetrakis(triphenylphosphine) palladium: inorganic Strong base (K 2 CO 3 ) molar ratio is 2:2~3:0.1~0.3:3~5; the volume ratio of toluene and tetrahydrofuran is 1~2:1~2. Under the usage ratio of the raw materials and the solvent and the solvent ratio, the degree of completion of the reaction is good and the yield is high. Under ni...

Embodiment 1

[0047] A method for preparing an efficient organic near-infrared fluorescent material, comprising:

[0048] (S1) Synthesis of intermediate benzothiadiazole derivatives (II):

[0049] Weigh (4-(2'-(4″-methoxyphenyl)amino)phenyl)boronic acid 2mmol (0.698g), 7-bromo-4-formylbenzothiadiazole 2mmol (0.486g), Four (triphenylphosphine) palladium 0.1mmol (0.116g), then add 3mmol (0.415g) K 2 CO 3 Dissolve in a mixed solution of 30mL toluene and 30mL tetrahydrofuran. Under nitrogen conditions, the temperature was raised to 90° C. for reflux reaction for 10 h.

[0050] After the reaction solution was cooled, extraction was performed, and the organic phases were combined, and dried by adding anhydrous magnesium sulfate. The residue obtained by filtration and concentration under reduced pressure was separated by silica gel column chromatography, the eluent was (petroleum ether / dichloromethane=3:1), and the dark red intermediate benzothiadiazole derivative was obtained after the solven...

Embodiment 2

[0060] (S1) Synthesis of intermediate benzothiadiazole derivatives (II):

[0061] Weigh (4-(2'-(4″-methoxyphenyl)amino)phenyl)boronic acid 2mmol (0.698g), 7-bromo-4-formylbenzothiadiazole 3mmol (0.729g), Four (triphenylphosphine) palladium 0.1mmol (0.116g), then add 3mmol (0.415g) K 2 CO 3 Dissolve in a mixed solution of 30mL toluene and 30mL tetrahydrofuran. Under nitrogen conditions, the temperature was raised to 90° C. for reflux reaction for 10 h.

[0062] After the reaction solution was cooled, extraction was performed, and the organic phases were combined, and dried by adding anhydrous magnesium sulfate. The residue obtained by filtration and concentration under reduced pressure was separated by silica gel column chromatography, the eluent was (petroleum ether / dichloromethane=3:1), and the dark red intermediate benzothiadiazole derivative was obtained after the solvent was rotary evaporated under reduced pressure. The compound (Ⅱ) was 0.832g, and the total yield was ...

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Abstract

The invention discloses a high-efficiency organic near-infrared fluorescent material and its preparation and application. The material has a structure shown in formula (I), the maximum fluorescence emission peak is 701nm, and the absolute quantum efficiency is 48.7%. The material prepared by the material Near-infrared fluorescent polymer hemisphere, which can generate near-infrared laser at 735.2nm, and has a low threshold of 22.3kW·cm ‑2 And narrow half-width characteristics, can be used in flaw detection, medical imaging and other fields.

Description

technical field [0001] The invention relates to a near-infrared fluorescent material, in particular to a high-efficiency organic near-infrared fluorescent material and its preparation and application. Background technique [0002] Near-infrared organic fluorescent materials have attracted extensive attention for their potential applications in organic electroluminescent semiconductors (OLEDs), crystal lasers (amplified spontaneous emission), solar cells, biological imaging, photothermal therapy, and detection and sensing. The near-infrared wavelength range is mainly located at 650-900nm. Compared with most traditional ultraviolet and visible light, near-infrared light has stronger penetrating power, less energy and non-destructive properties. Compared with inorganic materials and metal complex materials, the advantages of organic solid fluorescent materials are: lower cost, easy to modify, easy to degrade in vivo and so on. [0003] At present, there have been many reports ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/14C09K11/06A61K49/00
CPCA61K49/0021A61K49/0091C07D285/14C09K11/06C09K2211/1007C09K2211/1014C09K2211/1051
Inventor 吕春燕张玉建罗卿
Owner HUZHOU TEACHERS COLLEGE
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