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Bifunctional fluorescent probe adopting anthracene as matrix, as well as preparation method and application

A fluorescent probe, dual-function technology, applied in the field of fine chemicals, to achieve the effects of cheap raw materials, good selectivity, and obvious color change

Inactive Publication Date: 2015-07-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluorescent probes based on pyrene, 6,13-pentabenzoquinone, naphthalene, quinoline, and benzimidazole can well realize the fluorescence detection of iron ion and fluoride ion (Tetrahedron Lett.2010,51,5559-5562; Talanta , 2013,105,152-157; Tetrahedron,2011,67,7909-7912; Supramol.Chem.2015,27,224-232; Sens.Actuators, B 2013,186,657-665), and anthracene-based fluorescent probes with this function Not yet reported

Method used

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  • Bifunctional fluorescent probe adopting anthracene as matrix, as well as preparation method and application
  • Bifunctional fluorescent probe adopting anthracene as matrix, as well as preparation method and application
  • Bifunctional fluorescent probe adopting anthracene as matrix, as well as preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1 prepares fluorescent probe 1

[0033] (1) Synthesis of 9-anthracene methyl isocyanate

[0034] Dissolve 828mg of 9-anthracenemethylamine in 80mL of dichloromethane at room temperature, then add dropwise 8mL of dichloromethane solution containing 1.2g of triphosgene, and stir at room temperature for 1 hour; then add dropwise dichloromethane solution containing 808mg of triethylamine Methane solution 8mL, react for 24 hours; add saturated sodium bicarbonate to it to adjust the pH to neutral, separate the liquid, extract the water layer with dichloromethane, separate the liquid, wash the organic layer with water, dry the organic layer with magnesium sulfate, and obtain the intermediate 9-anthracene methyl isocyanate 800mg, yield 85%.

[0035] 1 H-NMR (400MHz, CDCl 3 ),8.51(s,1H),8.27(d,2H,J=8.0Hz),8.06(d,2H,J=8.0Hz),7.62(t,2H,J=8.0Hz),7.52(t,2H ,J=8.0Hz),5.36(s,2H,CH 2 );

[0036] HRMS: Calcd for [M-NCO] + ,191.0861; Found, 191.0852.

[0037] (2) Synth...

Embodiment 2

[0041] Embodiment 2 prepares fluorescent probe 2

[0042] (1) Synthesis of 9-anthracene methyl isothiocyanate

[0043] Dissolve 414mg of 9-anthracenemethylamine in 20mL of dichloromethane, then add 520mg of calcium carbonate and 20mL of water, and finally add 322mg of thiophosgene, and react at room temperature for 12 hours. Add saturated sodium bicarbonate solution to the reaction solution to adjust the pH to neutral, extract with dichloromethane, separate the layers, wash the organic layer with water, dry the organic layer with magnesium sulfate, and obtain the intermediate 9-anthracenemethyl isothiocyanate after rotary evaporation 380 mg, yield 76%.

[0044] 1 H-NMR (400MHz, CDCl 3 ),8.54(s,1H),8.24(d,2H,J=8.0Hz),8.07(d,2H,J=8.0Hz),7.64(t,2H,J=8.0Hz),7.54(t,2H ,J=8.0Hz),5.60(s,2H).

[0045] (2) Synthesis of fluorescent probe 2

[0046] Dissolve 260 mg of 9-anthracenemethyl isothiocyanate obtained in the previous step in 30 mL of ammonia (0.7 mol / L) tetrahydrofuran solut...

Embodiment 3

[0049] Embodiment 3. Fluorescent probe 1 and Fe under visible light and 365nm 3+ and F - effect

[0050] Accurately weigh 25 mg of fluorescent probe 1 and dissolve it in 10 mL of dimethyl sulfoxide, and take 1 mL of it and dissolve it in 99 mL of a mixed solution of dimethyl sulfoxide and water with a volume ratio of 1:1 to make a concentration of 10 -4 mol / L of test solution 1. Accurately measure 3mL of test solution 1 each time in three sample bottles of No. 1, No. 2 and No. 3, and then add 30 μL of ferric chloride with a concentration of 0.01mol / L to No. 2 and No. 3 sample bottles respectively Finally, add 30 μL of tetrabutylammonium fluoride dimethyl sulfoxide solution with a concentration of 0.01mol / L to sample bottle No. 3, and three samples of No. 1, No. 2 and No. 3 Shake the bottle evenly, and it can be obtained under visible light Figure 1a The results shown; can be obtained under UV 365nm Figure 1b The results shown.

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Abstract

The invention provides a bifunctional fluorescent probe which is provided with the structure of the general formula I and adopts anthracene as the matrix. The preparation method of the bifunctional fluorescent probe comprises the following steps: conducting isocyanic acid esterification or isothiocyanic acid esterification on 9-anthracene methylamine; conducting the nucleophilic addition reaction to obtain the bifunctional fluorescent probe. The bifunctional fluorescent probe has the good fluorescence detection effect on iron ions; moreover, the system composed of the bifunctional fluorescent probe and the iron ions has the selective fluorescence enhanced detection effect on fluorine ions.

Description

technical field [0001] The invention relates to a class of bifunctional fluorescent probe compounds with anthracene as the matrix, a preparation method and application thereof, and belongs to the detection of ions in the field of fine chemical industry. Background technique [0002] Iron is one of the necessary elements for the human body, and its role is irreplaceable. It is a cofactor of biological enzymes and plays a vital role in oxygen transport and metabolism. If the iron content is abnormal, it will lead to many diseases, such as: gastrointestinal cancer, hepatitis and Alzheimer's disease. Therefore, it is of great significance to detect the iron content in living organisms. Traditional methods for detecting iron ion content include atomic absorption spectrometry, resonance ionization mass spectrometry, isotope dilution, and chromatography. In recent years, due to the advantages of high sensitivity and fast response, fluorescence detection has attracted extensive a...

Claims

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Application Information

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IPC IPC(8): C07C275/24C07C273/18C07C335/12C09K11/06G01N21/64
Inventor 周宇涵曲景平董晓亮
Owner DALIAN UNIV OF TECH
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