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Preparation and application of sulfite ratiometric fluorescent probe

A ratio fluorescent probe, sulfite technology, applied in the field of chemical analysis and detection, to achieve the effect of simple synthesis, strong anti-interference ability and low cost

Active Publication Date: 2015-01-07
SUZHOU ROWLAND BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluorescent probes have the characteristics of high sensitivity, good selectivity, and in-situ detection, and are very suitable for detecting sulfite ions. Or weakened as a response signal, easily affected by factors such as the concentration of the detection substrate, the external environment and the sensitivity of the instrument

Method used

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  • Preparation and application of sulfite ratiometric fluorescent probe
  • Preparation and application of sulfite ratiometric fluorescent probe
  • Preparation and application of sulfite ratiometric fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the synthesis of compound 1

[0020]Dissolve o-aminothiophenol (8.2 g, 66 mmol) and 4-methylsalicylic acid (10.0 g, 66 mmol) in 70 mL of toluene, heat to 55 °C under nitrogen protection, and stir for 2.5 h; then stop heating , naturally lowered the temperature to 35°C, slowly added 6.2 mL of phosphorus trichloride dropwise to the reaction solution, raised the temperature to 85°C and stirred for 5 h; the reaction was stopped, the solvent was removed by rotary evaporation, and the product 1 was obtained by column chromatography. Yield: 6.4 g. Yield: 40.3%. Compound 1 is characterized as follows: 1 H NMR (CDCl 3 ): δ = 12.46 (s, 1H), 7.97-7.95 (d, 1H), 7.89-7.87 (d, 1H), 7.58-7.56 (d, 1H), 7.51-7.47 (t, 1H), 7.41-7.37 (t, 1H), 6.92 (s, 1H), 6.78-6.76 (d, 1H), 2.37 (s, 3H).

Embodiment 2

[0021] Embodiment 2: the synthesis of compound 2

[0022] The product 1 (5.0 g, 20.7 mmol) and triethylamine (2.5 g, 24.9 mmol) obtained in the previous step were dissolved in 60 mL of dichloromethane, and acetyl chloride (1.95 g, 24.9 mmol) was slowly added dropwise thereto, and stirred at room temperature for 2 h; stop the reaction, add 40 mL of water to quench the reaction, extract with dichloromethane, wash with saturated brine, dry over anhydrous sodium sulfate, remove the solvent by rotary evaporation, and separate the product 2 by column chromatography. Yield: 4.7 g. Yield: 80%. Compound 2 is characterized as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 8.23 ​​(d, J = 8.1 Hz, 1H), 8.11 (d, J = 8.1 Hz, 1H), 7.94 (d, J = 7.5 Hz, 1H), 7.53 (t, J = 7.7 Hz, 1H), 7.43 (m, 1H), 7.24 (d, J = 8.1, 1H), 7.09 (s, 1H), 2.51 (s, 3H), 2.46 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 169.31, 162.75, 153.05, 148.12, 142.45, 135.21, 130.07, 127.43, 126.26, 125.20, 124.17, 123.38, 123.23, 12...

Embodiment 3

[0023] Embodiment 3: the synthesis of compound 3

[0024] The product 2 obtained in the previous step ( 3.5 g, 12.4 mmol), N-bromosuccinimide (2.4 g, 13.5 mmol), benzoyl peroxide (0.06 g, 0.025 mmol) were dissolved in 50 mL of dry carbon tetrachloride, refluxed for 24 h Stop the reaction, pour the reaction solution into ice water, extract with chloroform, dry over anhydrous sodium sulfate, remove the solvent by rotary evaporation, and separate the product 3 by column chromatography after vacuum drying. Yield: 2.3 g. Yield: 51.3%. Compound 3 is characterized as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 8.35 (d, J = 8.1 Hz, 1H), 8.12 (d, J = 7.9 Hz, 1H), 7.96 (d, J = 7.4 Hz, 1H), 7.58 – 7.52 (m, 1H), 7.48 – 7.42 (m, 2H), 7.33 (s, 1H), 4.54 (s, 2H), 2.52 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 168.97, 161.79, 152.91, 148.23, 141.31, 135.35, 130.68, 127.00, 126.46, 126.03, 125.56, 124.31, 123.47, 121.39, 31.73, 21.

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Abstract

The invention discloses a novel compound capable of sulfite ion fluorescent identification, and particularly relates to a preparation method and application of a sulfite ratiometric fluorescent probe, belonging to the technical field of chemical analysis and detection. The molecular structural formula is disclosed in the specification. The fluorescent probe is used for fluorescent sensing and analysis of sulfite ions in an environmental or biological sample; after adding the sulfite, the formyl group and sulfite radical are subjected to addition reaction to generate hydroxy sulfonate; and the fluorescent probe has the advantages of favorable identification selectivity for sulfite ions and high interference resistance, can sensitively and quickly identify the sulfite ions from multiple anions, and has favorable application prospects.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a sulfite ratio fluorescent probe and the application of the fluorescent probe in detecting sulfite ions. Background technique [0002] Sulfite is an important food additive that acts as a food preservative and bleaching agent, and prevents food browning by inhibiting non-enzymatic and enzymatic browning. The use of sulfite needs to be within a certain safety range. A small amount of sulfite intake by humans will not cause harm to the body. However, excessive intake of sulfite may cause gastrointestinal disorders, severe abdominal pain, and renal dysfunction Can disease. Especially for people who are allergic to sulfites, even a small amount of sulfites can easily cause asthma, skin allergies, and gastrointestinal discomfort. In addition, industrial wastewater contains too much sulfite, which will seriously affect the concentratio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/24C09K11/06G01N21/64
CPCC07D277/66C09K11/06C09K2211/1007C09K2211/1037G01N21/643G01N21/6486
Inventor 宋相志刘兴江
Owner SUZHOU ROWLAND BIOTECH
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