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Red light emission fluorescent dye as well as preparation method and application thereof

A fluorescent dye, red light technology, applied in luminescent materials, chemical instruments and methods, pharmaceutical formulations, etc., can solve the problems of easy photobleaching, low quantum yield, difficulty in synthesizing red light emitting fluorescent dyes, etc., and achieve photostability Good properties, simple synthesis process and high fluorescence quantum yield

Inactive Publication Date: 2018-06-01
SUZHOU BAIYUAN GENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, the technical problem to be solved by the present invention is to overcome the defects in the prior art that the synthesis of red light-emitting fluorescent dyes is difficult, prone to photobleaching, and relatively low quantum yield.

Method used

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  • Red light emission fluorescent dye as well as preparation method and application thereof
  • Red light emission fluorescent dye as well as preparation method and application thereof
  • Red light emission fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation method of the red light-emitting fluorescent dye (II) provided in this embodiment:

[0026] Has formula (II) structure:

[0027]

[0028] Its preparation method is as follows:

[0029]

[0030] S1. Take 10.0mL of chloroacetyl chloride and 30.0mL of 4-bromo-2-pyrrole carboxylic acid into a 500mL single-necked bottle, use 50mL of dichloromethane as a solvent, stir magnetically at 25°C to 28°C for 25min to 30min, and conduct thin layer analysis After the reaction of the raw material 4-bromo-2-pyrrole carboxylic acid was completed, the developer was ethyl acetate:petroleum ether=1:1, and directly evaporated to dryness at 30°C to obtain intermediate A of fluorescent dye (II).

[0031] S2. Add 200mL of boron trifluoride ether solution to the above-mentioned one-mouth bottle, slowly add 20mL of triethylamine dropwise, stir with magnetic force, control the temperature at 0-5°C, after the dropwise addition of triethylamine is completed, rise to 25°C-28°C f...

Embodiment 2

[0043] The preparation method of the red light-emitting fluorescent dye (III) provided in this embodiment:

[0044] Has the structure of formula (III):

[0045]

[0046] Its preparation method is as follows:

[0047]

[0048] S1. Take 30.0mL of chloroacetyl chloride and 100.0mL of 4-bromo-2-pyrrole carboxylic acid into a 1000mL single-necked bottle, use 200mL of dichloromethane as solvent, stir magnetically at 25°C to 28°C for 25min to 30min, and conduct TLC analysis After the reaction of the raw material 4-bromo-2-pyrrole carboxylic acid was completed, the developer was ethyl acetate:petroleum ether=1:1, and directly evaporated to dryness at 30°C to obtain intermediate A of fluorescent dye (III).

[0049] S2. Add 200mL of boron trifluoride ether solution to the above-mentioned one-mouth bottle, slowly add 20mL of triethylamine dropwise, stir with magnetic force, control the temperature at 0-5°C, after the dropwise addition of triethylamine is completed, rise to 25°C-28°C...

Embodiment 3

[0061] The preparation method of the red light-emitting fluorescent dye (IV) provided in this embodiment:

[0062] Has formula (IV) structure:

[0063]

[0064] Its preparation method is as follows:

[0065]

[0066] S1. Take 15.0mL of chloroacetyl chloride and 50.0mL of 4-bromo-2-pyrrole carboxylic acid into a 500mL single-necked bottle, use 75mL of dichloromethane as solvent, stir magnetically at 25°C to 28°C for 25min to 30min, and conduct TLC analysis After the reaction of the raw material 4-bromo-2-pyrrole carboxylic acid was completed, the developer was ethyl acetate:petroleum ether=1:1, and directly evaporated to dryness at 30°C to obtain intermediate A of fluorescent dye (IV).

[0067] S2. Add 200mL of boron trifluoride ether solution to the above-mentioned one-mouth bottle, slowly add 20mL of triethylamine dropwise, stir with magnetic force, control the temperature at 0-5°C, after the dropwise addition of triethylamine is completed, rise to 25°C-28°C for reacti...

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Abstract

The invention relates to the field of optical function materials, in particular to a red light emission fluorescent dye. The structure of the fluorescent dye is shown as the formula (I) in the description, wherein R1 and R2 are independently selected from one of C1-C10 alkyl, aryl and heterocyclic rings. The fluorescent dye has narrow fluorescence emission spectrum, high molar absorption coefficient, high fluorescence quantum efficiency, good photostability and high sensitivity, realizes trace detection, can be used in different application fields such as cell imaging, fluorescence probes, laser dyes, fluorescence sensors and the like and shows good practicability. According to the preparation method, the technology is simple, the yield is high, and the prepared fluorescent dye is novel instructure, good in solubility, excellent in performance and suitable for being widely applied to the fields of biology, environment and the like.

Description

technical field [0001] The invention relates to the field of optical functional materials, in particular to a red light-emitting fluorescent dye and its preparation method and application. Background technique [0002] Dyes that can strongly absorb and radiate fluorescence in the visible light range are called fluorescent dyes. Each molecule has a series of strict discrete energy levels. Most of the material molecules are in the "ground state" at room temperature. When these substances are irradiated by light After absorbing light energy, it enters a new state called "excited state". The molecular weight in the "excited state" is unstable, and it can pass 10 -9 ~10 -7 In a very short period of time, the emitted light quantum returns to the ground state, and this process emits fluorescence. Since the 20th century, fluorescent dyes have been widely used in various industries such as textiles, plastic dyeing, and printing pigments. In recent years, fluorescent dyes have been...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02A61K49/00
CPCC09K11/06A61K49/0021C07F5/022
Inventor 车团结徐进章赵芳李力
Owner SUZHOU BAIYUAN GENT CO LTD
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