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Preparation and application of a 1,8-naphthoimide-based fluorescent molecular probe for hydrogen sulfide

A fluorescent molecular probe, naphthalimide technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis by optical means, etc., can solve the problems of limited application, narrow linear range, etc. High sensitivity and good specificity

Active Publication Date: 2022-05-10
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But most of them have only one recognition site, and the fluorescence intensity is related to H 2 The linear range of S concentration is narrow (between 0-20 μmmol / L), which limits its use at high concentrations of H 2 Applications in the S environment, so design new fluorescent molecular probes, broaden the H 2 The linear detection range of S is of great significance

Method used

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  • Preparation and application of a 1,8-naphthoimide-based fluorescent molecular probe for hydrogen sulfide
  • Preparation and application of a 1,8-naphthoimide-based fluorescent molecular probe for hydrogen sulfide
  • Preparation and application of a 1,8-naphthoimide-based fluorescent molecular probe for hydrogen sulfide

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Example 1: 1,8-naphthalimide H 2 Synthesis of S Fluorescent Molecular Probes

[0042] 1. Synthesis of N-(4-hydroxyphenyl)-4-bromo-1,8-naphthalimide (intermediate compound 1a):

[0043] Under the protection of nitrogen, 2.77g (10.00mmol) of 4-bromo-1,8-naphthalene dicarboxylic anhydride was dissolved in 50mL of absolute ethanol, and after stirring at room temperature, 1.31g (12.00mmol) of 4-aminophenol was added, Stirring was continued and the temperature of the reaction liquid was raised to 80° C., and the reaction was refluxed for 8 hours. After the complete conversion of the raw material was monitored by TLC (the developer was petroleum ether: ethyl acetate = 2:1, V / V), the heating was stopped, and the reaction liquid was cooled down. During the cooling process, solids could be observed to precipitate out gradually. Suction filtration, washing, and thorough drying afforded 3.34 g of a brown solid, with a yield of 90.76%.

[0044] 2. Synthesis of N-(4-hydroxyphenyl)...

Embodiment 2

[0055] Example 2: 1,8-naphthalimide H 2 Application of S Fluorescent Molecular Probes

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Abstract

The invention discloses a preparation method of a 1,8-naphthalimide hydrogen sulfide fluorescent molecular probe and its application in hydrogen sulfide identification and detection. The probe of the present invention uses N-(p-phenylmethyl)-4-hydroxyl-1,8-naphthalimide as a fluorescent matrix and 2,4-dinitrophenyl ether as a recognition group to obtain a double recognition site As a fluorescent molecular probe, hydrogen sulfide exposes the hydroxyl group of the fluorophore through thiolysis of 2,4-dinitrophenyl ether, thereby enhancing the fluorescence intensity (more than 30 times). The fluorescent molecular probe of the present invention has the advantages of stable photochemical properties, high fluorescence quantum yield and low price, and can specifically recognize hydrogen sulfide without being affected by Na + , Ca 2+ , NO 2 ‑ 、H 2 o 2 , ClO ‑ 、HSO 4 ‑ 、CN 2 h 4 S, HSO 3 ‑ , S 2 o 5 2‑ , S 2 o 8 2‑ With the interference of plasma, the linear detection range is increased to 0-40μmmol / L, which can be used for the quantitative detection of high-concentration hydrogen sulfide such as river water, rainwater, drinking water, drilling fluid, swamp fluid, etc., and has potential practical application value.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a preparation method of a novel 1,8-naphthalimide hydrogen sulfide fluorescent molecular probe and its application in hydrogen sulfide identification and detection. Background technique [0002] As one of the three major gas molecules, hydrogen sulfide (H 2 S) are closely related to human health, plant growth and environmental issues. In terms of human health, intracellular H 2 S plays an important role in the regulation of digestive system, nervous system, cardiovascular system and urinary system, H 2 S concentration imbalance can lead to arterial and pulmonary hypertension, Alzheimer's disease, bone damage, liver cirrhosis and other diseases. Exogenous H 2 S is also considered to be a highly toxic drug next to cyanide, and low concentrations of H 2 S can regulate the content of osmotic regulator factors in plants and maintain the plant's...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06G01N21/6428G01N21/643C09K2211/1029
Inventor 曲红梅刘丽强周晓露马芸霞张家寄
Owner TIANJIN UNIV
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