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Boric acid fluorescence molecular probe as well as preparation method and application thereof

A fluorescent molecular probe, boric acid technology, used in chemical instruments and methods, material analysis by optical means, analysis of materials, etc.

Active Publication Date: 2015-01-14
苏州高德瑞仪器有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, in some emerging research fields, the use of traditional analytical methods is often not sufficient, and in these fields, molecular probes will play a huge role

Method used

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  • Boric acid fluorescence molecular probe as well as preparation method and application thereof
  • Boric acid fluorescence molecular probe as well as preparation method and application thereof
  • Boric acid fluorescence molecular probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Fluorescent Probe Compounds 4 Synthesis:

[0048]

[0049] (1) compound 1 Synthesis

[0050] Add 2,4-dimethylpyrrole (3 ml, 30 mmol) and benzoyl chloride (2 mL, 18 mmol) into a 150 mL two-necked flask, and stir at room temperature for three days. Add triethylamine (13 mL, 90 mmol), BF 3 ×Et 2 O (15 mL, 120 mmol), stirred at room temperature for one day. The solvent was removed under reduced pressure. Separation by column chromatography (silica gel column, developing solvent is dichloromethane). A dark red sticky substance was obtained, which was recrystallized in methanol to obtain 800 mg of a red solid. Yield 13%.

[0051] (2) compound 2 Synthesis

[0052] In a 250 mL two-necked flask, ice-bathed and protected by argon, add 10 mL DMF and 10 mL phosphorus oxychloride. Stir at room temperature for 30 min. Add 100 mL dichloroethane, 1 (474 mg, 1.5 mmol), stirred at 50 °C for 3 h. The solvent was removed under reduced pressure, and the res...

Embodiment 2

[0057] Example 2 Fluorescent Probe Compounds 8 Synthesis:

[0058]

[0059] (2) compound 5 Synthesis

[0060] Add 2,4-dimethylpyrrole (3 ml, 30 mmol) and 4-diethylaminobenzoyl chloride (3.8 g, 18 mmol) into a 100 mL two-necked flask, and stir at room temperature for three days. Add triethylamine (13 mL, 90 mmol), BF 3 ×Et 2 O (15 mL, 120 mmol), and stirred at room temperature for one day. The solvent was evaporated under reduced pressure. Separation by column chromatography (silica gel column, developing solvent is dichloromethane). A dark red sticky substance was obtained, which was recrystallized in methanol to obtain 650 mg of a purple solid. Yield 8.9%.

[0061] (2) compound 6 Synthesis

[0062] In a 250 mL two-necked flask, ice-bathed and protected by argon, add 10 mL DMF and 10 mL phosphorus oxychloride. Stir at room temperature for 30 min. Add 100 mL dichloroethane, 5 (595 mg, 1.5 mmol), stirred at 50 °C for 3 h. The solvent was removed under reduc...

Embodiment 3

[0067] Example 3 Fluorescent Probe Compounds 12 Synthesis:

[0068]

[0069] (3) compound 9 Synthesis

[0070] Add 2,4-dimethylpyrrole (3 ml, 30 mmol) and 4-chlorobenzoyl chloride (3.2 g, 18 mmol) into a 100 mL two-necked flask, and stir at room temperature for three days. Add triethylamine (13 mL, 90 mmol), BF 3 ×Et 2 O (15 mL, 120 mmol), and stirred at room temperature for one day. The solvent was evaporated under reduced pressure. Separation by column chromatography (silica gel column, developing solvent is dichloromethane). A deep red viscous substance was obtained, which was recrystallized in methanol to obtain 720 mg of a purple solid. Yield 11%.

[0071] (2) compound 10 Synthesis

[0072] In a 250 mL two-necked flask, ice-bathed and protected by argon, add 10 mL DMF and 10 mL phosphorus oxychloride. Stir at room temperature for 30 min. Add 100 mL dichloroethane, 9 (540 mg, 1.5 mmol), stirred at 50 °C for 3 h. The solvent was removed under reduced...

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Abstract

The invention discloses a boric acid fluorescence molecular probe as well as a preparation method and an application thereof, belonging to the technical field of fine chemical engineering. The probe compounds are formed by performing simple chemical modification on bodipy fluorescent dyes. Boric acid groups in the bodipy-based fluorescent dye molecules can be firmly combined with analyte by virtue of a covalent bond, so that a problem that the common fluorescence probe cannot be used in an aqueous liquid is solved, and guiding significance is provided for designing fluorescence-enhanced type probe compounds which can be practically applied. Excitation wavelength and emission wavelength of the probe compounds are in a visible region; in a practical detecting range with a nearly neutral pH value, the boric acid fluorescence molecular probe has good selectivity on glucose, gluconic acid, tartaric acid and the like, and has good sensitivity. The probe compounds can be used for detecting glucose in a fluorescence manner, and have a potential application value in glucose detection in the processes such as medical production and industrial production.

Description

technical field [0001] The invention relates to a boric acid fluorescent molecular probe and its preparation method and application. The compound is suitable for the fluorescence detection of sugar acid compounds such as tartaric acid and mandelic acid, and belongs to the technical field of fine chemicals. Background technique [0002] In the field of rapid detection, molecular probes are an example of the application of knowledge of supramolecular chemistry and are an emerging discipline. The research on molecular probe chromogenic analysis for small organic molecules or inorganic ions is a hotspot in current molecular recognition research. Sugars, sugar acids and their related molecules are of great significance in the metabolism of biological organisms, as well as in the diagnosis and treatment of diseases (such as diabetes, etc.). Identifying sugars and sugar-acid compounds in biological organisms and quantitatively testing their concentrations in aqueous solutions are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/02C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055G01N21/643
Inventor 赵建章崔京南王肇
Owner 苏州高德瑞仪器有限公司
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