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Near-infrared fluorescent dye and application thereof in detection of SO3 < 2->/HSO3 <->

A fluorescent dye and near-infrared technology, applied in the field of fluorescent dyes, can solve the problems of poor solubility, long emission wavelength, poor stability, etc., and achieve the effects of avoiding fluorescence interference, simple preparation and strong penetrating power.

Active Publication Date: 2022-02-01
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems of poor stability, short emission wavelength and poor solubility of traditional fluorescent dyes, the present invention aims to improve and improve the photophysical and photochemical properties of fluorescent dyes, and constructs a series of new fluorescent dyes through hybridization strategy, especially Obtained two kinds of near-infrared fluorescent dyes (in mixed solvent (VDMSO: VPBS=3:7), SZ-1 emission wavelength 699nm, MZ-1 emission wavelength 656nm), these two kinds of near-infrared dyes have light, heat Good stability, good solubility, long emission wavelength and other excellent characteristics, and the preliminary application of these dyes in the design and development of probes

Method used

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  • Near-infrared fluorescent dye and application thereof in detection of SO3 &lt; 2-&gt;/HSO3 &lt;-&gt;
  • Near-infrared fluorescent dye and application thereof in detection of SO3 &lt; 2-&gt;/HSO3 &lt;-&gt;
  • Near-infrared fluorescent dye and application thereof in detection of SO3 &lt; 2-&gt;/HSO3 &lt;-&gt;

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the synthesis of compound MZ-1

[0037] Weigh 50mg (0.22mol) of 6-(diethylamino)quinoline-2-carbaldehyde and 34.4mg (0.22mol) of 2-cyanomethyl benzimidazole and join in the 25ml reaction flask, add 13.2mg (0.22 mol) of acetic acid was dissolved by adding 2ml of absolute ethanol and stirred at room temperature for 3.5 hours. The reaction was monitored by TLC spotting until the reaction of the raw materials was complete, filtered under reduced pressure, and washed to obtain 55mg of a red solid with a yield of 68%.

Embodiment 2

[0038] Embodiment 2: the synthesis of compound MZ-2

[0039] Weigh 50mg (0.32mol) of quinoline-2-carbaldehyde and 50.24mg (0.32mol) of 2-cyanomethylbenzimidazole into a 25ml reaction flask, add 19.2mg (0.32mol) of acetic acid, and then add 2ml Dissolve in absolute ethanol, stir at room temperature for 3.5 hours, and monitor the reaction by TLC spotting until the reaction of the raw materials is complete. After vacuum filtration and washing, 73 mg of black solid was obtained, with a yield of 77%.

Embodiment 3

[0040] Embodiment 3: the synthesis of compound MZ-3

[0041] Weigh 50mg (0.267mol) of 6-methoxyquinoline-2-formaldehyde and 42mg (0.267mol) of 2-cyanomethylbenzimidazole and join in a 25ml reaction flask, add 16mg (0.32mol) of acetic acid, Then add 2 ml of absolute ethanol to dissolve, stir at room temperature for 3.5 hours, and monitor the reaction by TLC spotting until the reaction of the raw materials is complete. After vacuum filtration and washing, 76 mg of green solid was obtained, with a yield of 87%.

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Abstract

The invention discloses a series of near-infrared fluorescent dyes and application thereof in detection of SO3 < 2-> / HSO3 <->. The probe provided by the invention shows near-infrared fluorescence in a mixed solution of DMSO and PBS, the wavelength of the probe is further subjected to red shift along with the increase of the proportion of the PBS solution, and the probe can be subjected to specific reaction with SO2 to generate obvious fluorescence blue shift change, so that specific response to SO2 is realized. The probe has good stability, is simple to prepare, can be stored and used for a long time, and also has good selectivity to SO2.

Description

technical field [0001] The patented technology belongs to the field of fluorescent dyes, and specifically relates to the preparation and application of near-infrared fluorescent dyes. Background technique [0002] Fluorescent dyes are an important branch of dye chemistry. In recent decades, fluorescent dyes and their derivatives have made many breakthroughs in materials, biology, medicine, etc., and have gradually become a key research direction in dye chemistry. [0003] With the rapid development of analytical chemistry, biological science, life science, medicine and other disciplines, organic fluorescent dyes have been widely used in many aspects such as biomolecular labeling, enzyme analysis, environmental analysis, cell staining and clinical laboratory diagnosis. It is an indispensable fluorescent signal reporting group in science, environmental science and medical research. Therefore, the development of functional organic fluorescent dyes with practical value has bec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06C07D417/06C09B23/10C09K11/06G01N21/64
CPCC07D401/06C07D417/06C09K11/06C09B23/0058C09B23/102C09B23/105G01N21/6428G01N21/6456C09K2211/1029C09K2211/1044C09K2211/1037
Inventor 郑开波余威王丽红李鋆肖宇峰
Owner CHINA THREE GORGES UNIV