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Fluorescent probe for detecting HClO and SO2 with high selectivity and high sensitivity

A high-sensitivity, fluorescent probe technology, used in fluorescence/phosphorescence, luminescent materials, measurement devices, etc., to solve problems such as inability to distinguish detection

Active Publication Date: 2021-04-27
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The object of the present invention is to provide a kind of highly selective, highly sensitive detection HClO and SO 2 The fluorescent probe solves the problem that the existing benzopyrrole-coumarin fluorescent probe cannot combine HClO with SO 2 Quick, clear distinction between detection of technical issues

Method used

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  • Fluorescent probe for detecting HClO and SO2 with high selectivity and high sensitivity
  • Fluorescent probe for detecting HClO and SO2 with high selectivity and high sensitivity
  • Fluorescent probe for detecting HClO and SO2 with high selectivity and high sensitivity

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Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of compound 2

[0035] Compound 1 (1.145g, 5.0mmol), 1-bromobutane (2.72g, 20.0mmol) and sodium hydroxide (1.6g, 40mmol) were dissolved in 15.0mL dimethyl sulfoxide, and potassium iodide (0.04g , 0.24mmol), heated to reflux for 3 hours, stopped the reaction, cooled to room temperature, poured the reaction solution into 50mL saturated brine, extracted with dichloromethane (50.0mL×3), dried over anhydrous sodium sulfate, and spin-dried under reduced pressure to obtain crude Product, finally through column chromatography (silica gel 200-300 mesh, eluent: V 石油醚 / V 乙酸乙酯=20 / 1) Compound 2 was isolated as a yellow oil, 1.326 g, yield 93%.

Embodiment 2

[0036] Embodiment 2: the synthesis of compound 3

[0037] Take 5mL of N,N-dimethylformamide and stir it in an ice bath, add 2mL of phosphorus oxychloride dropwise, protect it under argon, and stir with an orange-red color, then dissolve compound 2 (1.326g, 4.7mmol) in 5.0 In mL of anhydrous N,N-dimethylformamide, react at 80°C for 1 h, stop the reaction, cool to room temperature, pour the reaction solution into 50 mL of ice water, adjust the pH to neutral with sodium hydroxide, and extract with dichloromethane ( 50.0mL×3), washed with saturated brine, dried over anhydrous sodium sulfate, and spin-dried under reduced pressure to obtain the crude product, which was then subjected to column chromatography (eluent: V 石油醚 / V 乙酸乙酯 =15 / 1) The product was isolated, 1.24 g; yield 85%.

Embodiment 3

[0038] Embodiment 3: the synthesis of compound 4

[0039] Add aluminum powder (0.3g, 11.11mmol) to 15mL of acetonitrile, stir in an ice bath, then slowly add iodine (3 g, 11.81mmol), stir until a brownish black solid appears, then add compound 3 (1.24g, 3.96mmol) , heated to reflux for 3 hours, stopped the reaction, cooled to room temperature, suction filtered and washed alternately with water and ethyl acetate, dried over anhydrous sodium sulfate, and spin-dried under reduced pressure to obtain a crude product, which was finally subjected to column chromatography (silica gel 200-300 mesh, Eluent: V 石油醚 / V 乙酸乙酯 =10 / 1) Compound 4 was isolated as dark yellow oil, 1.056 g, yield 89%.

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Abstract

The invention relates to a fluorescent probe for detecting HClO and SO2 with high selectivity and high sensitivity, and belongs to the field of fluorescent probes. The molecular structure is shown in the specification, wherein R1 is N(CH2CH3)2 and is named as PBC1, and R2 is OH and is named as PBC2. The probe molecule does not have fluorescence and respectively emits green fluorescence and red fluorescence after reacting with HClO and SO2. The probe molecule disclosed by the invention not only can qualitatively analyze HClO and SO2, but also can realize rapid and quantitative detection of HClO and SO2, and has important application value in the fields of biochemistry and the like.

Description

[0001] The invention relates to a class of fluorescent probes based on benzopyrrole-coumarin, including its preparation, research on photophysical properties and application in the field of biological imaging, and belongs to the field of fluorescent probes. Background technique [0002] Reactive sulfur species (RSS) and reactive oxygen species (ROS) play key roles in a range of physiological and pathological processes, such as in cell proliferation, regulation of redox homeostasis, neurodegenerative injury and cytoprotection. As a signaling molecule, sulfur dioxide (SO 2 ) can be produced by the oxidation of hydrogen sulfide or sulfur-containing amino acids, and the decomposition of bisulfite pyruvate, in the form of HSO 3 - / SO 3 2- form exists in living organisms. There is increasing evidence that SO 2 Plays a vital role as an antioxidant in regulating intracellular redox. However, the unusual SO 2 Levels can cause lung cancer, cardiovascular disease, and neurological...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C09K11/06G01N21/64
CPCC07D513/04C09K11/06G01N21/6428C09K2211/1037C09K2211/1088G01N2021/6432G01N2021/6439
Inventor 王本花杨升韩金良任晓杰宋相志
Owner CENT SOUTH UNIV
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