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

A technology for exciting fluorescence and dyes, applied in luminescent materials, azo dyes, organic dyes, etc., can solve the problem of difficulty in the synthesis of red light-excited fluorescent dyes, improve sensitivity and selectivity, enhance the fluorescence and photostability of organic molecules Good results

Pending Publication Date: 2018-06-08
SUZHOU BAIYUAN GENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, the technical problem to be solved by the present invention is to overcome the difficulty in the synthesis of red light-excited fluorescent dyes in the prior art.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation method of the red light-excited fluorescent dye (II) provided in this example:

[0035] Has formula (II) structure:

[0036]

[0037] Its preparation method is as follows:

[0038]

[0039] (1) Preparation of intermediate 1-II

[0040] Under nitrogen protection, add 1.9g (0.01mol) of anhydrous CuI and 20ml THF to a 250ml reaction flask, cool to -55°C, add ClCH dropwise 2 CH=CHLi 1.23g (0.015m01), stirred for 35min, continued to cool to -80°C, added dropwise 2-chloro-4-methyl-2H-pyrrole 0.58g (0.005mol) in 60ml tetrahydrofuran solution, after the reaction, use 50ml of ethylene glycol dimethyl ether was diluted, washed with deionized water, and concentrated to obtain intermediate 1-II.

[0041] (2) Preparation of Intermediate 2-II

[0042] Add 1.2g (0.009mol) of anhydrous aluminum chloride and 24ml of dichloromethane into a 50ml reaction flask, place in an ice-salt bath, stir, cool down to 0°C, add 0.47g (0.003mol) of intermediate 1-II, Continue...

Embodiment 2

[0053] The preparation method of the red light-excited fluorescent dye (III) provided in this example:

[0054] Has the structure of formula (III):

[0055]

[0056] Its preparation method is as follows:

[0057]

[0058] (1) Preparation of intermediate 1-III

[0059] Under nitrogen protection, add anhydrous CuI 5.7g (0.03mol) and 50ml THF to a 500ml reaction flask, cool to -50°C, add ClCH dropwise 2 CH=CHLi 4.1g (0.05mol), stirred for 40min, continued to cool to -78°C, added dropwise a solution of 1.7g (0.015mol) of 2-chloro-4-methyl-2H-pyrrole in 200ml tetrahydrofuran, after the reaction, use Diluted with 200ml of ethylene glycol dimethyl ether, washed with deionized water, and concentrated to obtain intermediate 1-III.

[0060] (2) Preparation of Intermediate 2-III

[0061] Add 3.3g (0.025mol) of anhydrous aluminum chloride and 66ml of dichloromethane into the reaction flask, place in an ice-salt bath, stir, cool down to -3°C, add 1.6g (0.01mol) of intermediate 1-...

Embodiment 3

[0072] The preparation method of the red light-excited fluorescent dye (IV) provided in this embodiment:

[0073] Has formula (IV) structure:

[0074]

[0075] Its preparation method is as follows:

[0076]

[0077] (1) Preparation of intermediate 1-IV

[0078] Under the protection of nitrogen, add anhydrous CuI 9.5g (0.05mol) and 100ml THF to a 1000ml reaction flask, cool to -50°C, add ClCH dropwise 2 CH=CHLi 6.2g (0.075mol), stirred for 30min, continued to cool to -75°C, added dropwise 2.9g (0.025mol) of 2-chloro-4-methyl-2H-pyrrole in 300ml tetrahydrofuran solution, after the reaction, use 250ml of ethylene glycol dimethyl ether was diluted, washed with deionized water, and concentrated to obtain intermediate 1-IV.

[0079] (2) Preparation of intermediate 2-IV

[0080] Add 5.3g (0.04mol) of anhydrous aluminum chloride and 130ml of dichloromethane into the reaction flask, place in an ice-salt bath, stir, cool down to -2°C, add 7.4g (0.02mol) of intermediate 2-IV, ...

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Abstract

The invention relates to the field of photo-functional materials, in particular to a red light excited fluorescent dye. The red light excited fluorescent dye has a structure shown as the formula (I) in the description. The red light excited fluorescent dye has quite wide excitation spectrum, is good in photostability and high in 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, raw material cost is low, nopollution is produced, the process is simple, and yield is high; the prepared fluorescent dye is novel in structure, good in performance and suitable for being widely applied in 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-excited 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. Fluorescent dyes emit visible fluorescence after absorbing red light and emit visible fluorescence with longer wavelengths after absorbing visible light with shorter wavelengths. 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 absorb light energy under the irradiation of light, they enter a new state, called the "excited state", in the " Excited state" molecular weight is unstable, 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09B57/00G01N21/64H01L51/00H01L51/50H01L51/54H10K99/00
CPCG01N21/6428G01N21/6486C09K11/06C09B57/00C09K2211/1055C09K2211/1092C09K2211/1007C09K2211/1022C09K2211/1029H10K85/655H10K85/657H10K50/10G01N21/64
Inventor 车团结徐进章赵芳
Owner SUZHOU BAIYUAN GENT CO LTD
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