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A fluorescent probe for rapid detection of phosgene with high sensitivity and its synthesis method and application

A fluorescent probe, high-sensitivity technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high detection limit, poor selectivity, slow response speed containing phosgene, etc., and achieve low detection limit , the effect of high selectivity and good development prospects

Active Publication Date: 2022-03-01
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Most of the reported fluorescent probes have slow response to phosgene, high detection limit and poor selectivity

Method used

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  • A fluorescent probe for rapid detection of phosgene with high sensitivity and its synthesis method and application
  • A fluorescent probe for rapid detection of phosgene with high sensitivity and its synthesis method and application
  • A fluorescent probe for rapid detection of phosgene with high sensitivity and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of fluorescent probe DATPE

[0029] A magnetic stirring bar was added to a 100 mL round bottom flask, and the compound of formula (2) (0.4 g, 0.62 mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (1:2, V / V). Sodium borohydride (0.07 g, 1.85 mmol) was added to the reaction flask, followed by cobalt chloride hexahydrate (0.015 g, 0.06 mmol) with rapid stirring. The reaction was stirred at 90°C for 3 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50 mL×2). The organic layer was collected and washed with water (100 mL×5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified using silica gel column chromatography (dichloromethane / ethyl acetate, 50 / 1, V / V) to obtain the fluorescent probe DATPE as a light green solid (0.2 g, 0.32 mmol). The yield was 52%.

[0030] The proton nuclear magnetic resonanc...

Embodiment 2

[0032] Embodiment 2: the synthesis of fluorescent probe DATPE

[0033] A magnetic stirring bar was added to a 100 mL round bottom flask, and the compound of formula (2) (0.4 g, 0.62 mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (2:1, V / V). Sodium borohydride (0.07 g, 1.85 mmol) was added to the reaction flask, followed by cobalt chloride hexahydrate (0.015 g, 0.06 mmol) with rapid stirring. The reaction was stirred at 90°C for 3 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50 mL×2). The organic layer was collected and washed with water (100 mL×5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified using silica gel column chromatography (dichloromethane / ethyl acetate, 50 / 1, V / V) to obtain the fluorescent probe DATPE as a light green solid (0.2 g, 0.32 mmol). The yield was 45%.

[0034] The light green solid product prepar...

Embodiment 3

[0035] Embodiment 3: the synthesis of fluorescent probe DATPE

[0036] A magnetic stirring bar was added to a 100 mL round bottom flask, and the compound of formula (2) (0.4 g, 0.62 mmol) was dissolved in a mixed solvent of tetrahydrofuran and ethanol (1:2, V / V). Sodium borohydride (0.07 g, 1.85 mmol) was added to the reaction flask, followed by cobalt chloride hexahydrate (0.015 g, 0.06 mmol) with rapid stirring. The reaction was stirred at 90°C for 5 hours. After that, the reaction mixture was cooled to room temperature and extracted with dichloromethane (50 mL×2). The organic layer was collected and washed with water (100 mL×5), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The crude product was further purified using silica gel column chromatography (dichloromethane / ethyl acetate, 50 / 1, V / V) to obtain the fluorescent probe DATPE as a light green solid (0.2 g, 0.32 mmol). The yield was 50%.

[0037] The light green solid product prepar...

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Abstract

The invention discloses a high-sensitivity fluorescent probe for rapidly detecting phosgene and its synthesis method and application. The probe compound is 3,6-bis(1,2,2-tristyryl)benzene-1, 2-diamine, named after DATPE, its structural formula is as shown in formula (1), is to use o-phenylenediamino as phosgene reaction site, two (tristyryl) as fluorescent chromophore; Its synthetic method is benzene Ring-opening reaction for the reduction of thiadiazole units to o-phenylenediamino groups. The probe DATPE of the present invention can be solidified and applied on filter paper to prepare detection test paper, so as to realize real-time and visual monitoring of phosgene in the gas phase. The probe DATPE and the test strip thereof of the present invention have the advantages of high sensitivity, good selectivity, portability and the like for phosgene detection, and the synthesis method has simple steps and mild reaction conditions, and has good development prospects.

Description

technical field [0001] The invention belongs to the technical field of highly toxic and dangerous gas detection, and relates to a fluorescent probe, in particular to a fluorescent probe for rapidly detecting phosgene with high sensitivity, a synthesis method and an application thereof. Background technique [0002] Phosgene (COCl 2 ) is a highly toxic gas with suffocating properties. Exposure to phosgene can irritate the eyes and skin. Inhalation of phosgene can cause pulmonary edema, acute respiratory distress syndrome, and even death in severe cases. At the same time, phosgene is an important chemical basic raw material, which is widely used in industrial chemical processes to produce various organic intermediates, pesticides and pharmaceuticals. Accidental leakage in industrial production may be used in chemical terrorist attacks, posing a serious threat to the environment and public safety. Therefore, it is of great significance to develop a convenient, fast and reliab...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/51C07C209/00C07C209/84C09K11/06G01N21/64
CPCC07C211/51C07C209/00C07C209/84C09K11/06G01N21/643C09K2211/1007
Inventor 李秋艳程轲王晓军
Owner XUZHOU NORMAL UNIVERSITY
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