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Near-infrared fluorescent dye and preparation method thereof

A fluorescent dye and near-infrared technology, applied in the direction of oxazine dyes, organic dyes, luminescent materials, etc., can solve the problems of restricting the application of dyes, difficult to modify, easy to aggregate, etc., and achieve good application prospects, high profits, and good solubility.

Active Publication Date: 2019-09-27
LULIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the current commercial near-infrared fluorescent dyes, there are still some defects, such as poor stability, easy aggregation, poor solubility, difficult to modify, etc., which greatly limit the application of such dyes in various industries

Method used

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  • Near-infrared fluorescent dye and preparation method thereof
  • Near-infrared fluorescent dye and preparation method thereof
  • Near-infrared fluorescent dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] This embodiment provides a kind of near-infrared fluorescent dye, and its structural formula is as shown in (a):

[0034]

[0035] The synthetic route of described near-infrared fluorescent dye is shown in (b):

[0036]

[0037] The preparation method of described near-infrared fluorescent dye comprises the following steps:

[0038] (1) Xiangcong H 2 SO 4 Add N,N-diethyl-3-hydroxyaniline, stir to dissolve the raw material, add NaNO 3 , continue to stir until the reaction is complete, pour the reaction solution into ice water, a large amount of brownish-yellow solid is precipitated, filter under reduced pressure, wash the filter cake with deionized water, and dry in vacuum to obtain the filter cake compound;

[0039] (2) Dissolve the filter cake compound obtained in step (1) in ethanol, react in a hydrogen atmosphere, remove the hydrogen when the color of the reaction solution becomes colorless, allow air to enter the reaction bottle, and the color of the soluti...

Embodiment 2

[0041] This embodiment provides a kind of near-infrared fluorescent dye, and its structural formula is as shown in (a):

[0042]

[0043] The synthetic route of described near-infrared fluorescent dye is shown in (b):

[0044]

[0045] The preparation method of described near-infrared fluorescent dye comprises the following steps:

[0046] (1) In an ice bath, add 40 mL of concentrated H 2 SO 4 Add 30mmol of N,N-diethyl-3-hydroxyaniline, stir to dissolve the raw material, keep ice bath and add 33mmol of NaNO 3 , continue to stir at room temperature for 7 hours. After the reaction is completed, slowly pour the reaction solution into 200mL of ice water, and a large amount of brown-yellow solid is precipitated. After vacuum filtration, the filter cake is washed repeatedly with deionized water for at least three times, and vacuum-dried to obtain the filter cake compound ;

[0047](2) Dissolving the filter cake compound in ethanol, adding palladium carbon as a catalyst, re...

Embodiment 3

[0049] This embodiment provides a kind of near-infrared fluorescent dye, and its structural formula is as shown in (a):

[0050]

[0051] The synthetic route of described near-infrared fluorescent dye is shown in (b):

[0052]

[0053] The preparation method of described near-infrared fluorescent dye comprises the following steps:

[0054] (1) Under ice-bath conditions, in the presence of concentrated H 2 SO 4 (40mL) into a 100mL round bottom flask, add N,N-diethyl-3-hydroxyaniline (4.9573g, 30mmol), stir vigorously to dissolve the raw material, keep the ice bath and slowly add NaNO 3 (2.805g, 33mmol), stirred at room temperature for 7h, after the reaction was completed, the reaction solution was slowly poured into 200mL of ice water, a large amount of brown-yellow solid was precipitated, filtered under reduced pressure, and the filter cake was washed repeatedly with deionized water (50mL*3), Vacuum dry.

[0055] (2) The obtained filter cake compound is dissolved in ...

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Abstract

The invention relates to near-infrared fluorescent dye and a preparation method thereof. The novel phenoxazone near-infrared fluorescent dye is quickly and efficiently synthesized by a nitration reaction, a hydrogenous reduction method and an air oxidation method. The preparation method is environmentally friendly, industrialized production difficulty is low, and the profit is high; the near-infrared fluorescent dye involved in the invention has the characteristics of near infrared emission, high quantum yield with the yield reaching up to 27.55%, excellent dyeing property, good solubility and simple synthesis and preparation, can be widely applied to the aspects of bioimaging techniques, fluorescent probe kits, antibody and protein labelings, tumor targeting markers and drug modification and development, has very good application prospects, can also be widely applied to the industries of anti-counterfeiting printing, pesticides, dyes, building and food testing, and the like at the same time, and has relatively high application value.

Description

technical field [0001] The invention belongs to the technical field of dye processing, and in particular relates to a phenoxazinone near-infrared fluorescent dye and a preparation method thereof. Background technique [0002] Near-infrared fluorescence has the characteristics of strong tissue penetration, low background fluorescence interference, and small photodamage to biological samples, which has attracted more and more attention. However, in practical applications, some near-infrared fluorescent dyes have defects such as easy polymerization, poor solubility, difficult synthesis and low quantum yield. [0003] In recent years, organic small molecule fluorescent dyes have been widely used in photocatalysis, photoelectric materials, analysis and detection, biomolecular labeling, clinical diagnosis, etc. They are indispensable tools in chemistry, materials science, environmental science and biomedical research. In the current commercial near-infrared fluorescent dyes, ther...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09B19/00C07D265/38
CPCC09K11/06C09B19/00C07D265/38C09K2211/1033
Inventor 刘涛赵文静张明昇
Owner LULIANG UNIV
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