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Synthesis method and application of ratiometric fluorescent molecular probe for simultaneously detecting fluorine ion and sulfite radical

A fluorescent molecular probe and sulfite technology, applied in the field of chemical analysis and detection, to achieve the effects of high synthesis yield, easy availability of raw materials, and high sensitivity

Inactive Publication Date: 2015-05-13
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently, few fluorescent probes with dual functions have been reported.

Method used

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  • Synthesis method and application of ratiometric fluorescent molecular probe for simultaneously detecting fluorine ion and sulfite radical
  • Synthesis method and application of ratiometric fluorescent molecular probe for simultaneously detecting fluorine ion and sulfite radical
  • Synthesis method and application of ratiometric fluorescent molecular probe for simultaneously detecting fluorine ion and sulfite radical

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Preparation of 2-(4-methyl-2-hydroxyphenyl)-benzothiazole

[0043] According to the method reported in the literature, 2-(4-methyl-2-hydroxyphenyl)-benzothiazole was synthesized. Weigh 8.2g (66mmol) o-aminothiophenol and 10.0g (66mmol) 4-methylsalicylic acid in 70ml of toluene, heat to 50-55°C under the protection of nitrogen, and stir for about 2.5h. Then, the temperature was lowered to about 35°C, and 6.2ml of phosphorus trichloride was slowly added dropwise to the above system. After the dropwise addition of the phosphorus trichloride, the mixed solution became white and viscous. Continue to heat to 85°C and stir for 5 hours. , The system becomes a clear solution. After the reaction is complete, spin off the solvent and separate by column chromatography (dichloromethane: petroleum ether = 1:10) to obtain 6.4 g of 2-(4-methyl-2-hydroxyphenyl)-benzothiazole with a yield It is 40.3%.

Embodiment 2

[0044] Example 2: Preparation of 2-(4-methyl-2-acetoxyphenyl)benzothiazole (Compound 5)

[0045] Weigh 5.0g (20.7mmol) of 2-(4-methyl-2-hydroxyphenyl)-benzothiazole dissolved in 60ml of dichloromethane, add 2.5g (24.9mmol) of triethylamine, stir for 5min, 1.95g (24.9mmol) of acetyl chloride was added to the system, stirred at room temperature for 2h, monitored by TLC spot plate, and found that the raw material spots basically disappeared. The reaction was quenched by adding 40 ml of water, extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, spin-dried the solvent, and separated and purified by column chromatography (ethyl acetate: petroleum ether = 1:16) to obtain 4.7 g of compound 5. The yield was 80%. 1 H NMR(400MHz, CDCl 3 )δ8.23(d, J=8.1Hz, 1H), 8.11(d, J=8.1Hz, 1H), 7.94(d, J=7.5Hz, 1H), 7.53(t, J=7.7Hz, 1H) , 7.46-7.39 (m, 1H), 7.24 (d, J=8.1, 1H), 7.09 (s, 1H), 2.51 (s, 3H), 2.46 (s, 3H).

Embodiment 3

[0046] Example 3: Preparation of 2-(4-bromomethyl-2-acetoxyphenyl)benzothiazole (Compound 4)

[0047] Weigh 3.5g (12.4mmol) of compound 5, 0.06g (0.025mmol) of benzoyl peroxide, and 2.4g (13.5mmol) of N-bromosuccinimide dissolved in 50ml of dry carbon tetrachloride solution, and reflux Stir for 24h. After the reaction, the mixture was poured into ice water, extracted with chloroform, dried over anhydrous sodium sulfate, spin-dried the solvent, and separated and purified by column chromatography (ethyl acetate: petroleum ether = 1:14) to obtain 2.3 g of compound 4, with a yield It is 51.3%. 1 H NMR(400MHz, CDCl 3 )δ8.35 (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).

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Abstract

The invention relates to a synthesis method and application of a ratiometric fluorescent molecular probe for simultaneously detecting a fluorine ion and a sulfite radical. The ratiometric fluorescent molecular probe adopts a 2-(2-hydroxyphenyl)benzothiazole derivative as a matrix structure, and detects the fluorine ion and the sulfite radical based on excited-state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) mechanisms, respectively. The probe has a maximum emission wavelength of 498 nm in an acetonitrile solution with a concentration of 80%, when the fluorine ion is added, the fluorescence spectrum of the probe has a red shift of 136 nm; and when the sulfite radical is added, the fluorescence spectrum of the probe has a blue shift of 127 nm. The differentiated detection of the two ions can be realized by the fact that the fluorescence spectrum of the probe has an obvious red shift or blue shift after the fluorine ion or sulfite radical is added, respectively, showing different fluorescence response signals. The inventive fluorescent probe has the advantages of simple operation, mild reaction conditions, easy purification, high synthesis yield, good selectivity, high sensitivity and stable optical performances. At the same time, the design and synthesis of the fluorescent probe provide an important foundation for development of multi-functional fluorescent probes in the future.

Description

Technical field [0001] The present invention relates to the technical field of chemical analysis and detection, in particular to a method for preparing a ratio-based dual-function fluorescent molecular probe for simultaneous detection of fluoride ion and sulfite, and the use of the fluorescent molecular probe in detecting fluoride ion and sulfite application. Background technique [0002] The fluoride ion has a small radius, strong electronegativity, and special chemical properties, which arouses great interest among researchers. In addition, fluorine, as one of the essential trace elements for human life activities, plays an important role in the prevention of dental caries and the clinical treatment of osteoporosis. However, excessive intake of fluoride in the body can easily induce diseases such as dental fluorosis, skeletal fluorosis, kidney stones and renal dysfunction. As an important food additive, sulfite is widely used in the food industry. Due to its various energy ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F7/18G01N21/64
Inventor 宋相志磨玲娜
Owner CENT SOUTH UNIV
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