Preparation and application of 1, 8-naphthalimide hydrogen sulfide fluorescent molecular probe

A technology of fluorescent molecular probes and naphthalimides, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means. It can solve the problems of limited application and narrow linear range, and achieve economical and cheap High sensitivity, good specific effect

Active Publication Date: 2021-06-25
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

Method used

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  • Preparation and application of 1, 8-naphthalimide hydrogen sulfide fluorescent molecular probe
  • Preparation and application of 1, 8-naphthalimide hydrogen sulfide fluorescent molecular probe
  • Preparation and application of 1, 8-naphthalimide hydrogen sulfide fluorescent molecular probe

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 application of the 1, 8-naphthalimide hydrogen sulfide fluorescent molecular probe in hydrogen sulfide recognition and detection. The fluorescent molecular probe with double recognition sites is obtained by using N-(p-benzyl)-4-hydroxy-1, 8-naphthalimide as a fluorescent matrix and 2, 4-dinitrophenyl ether as a recognition group, hydrogen sulfide performs thiolysis on the 2, 4-dinitrophenyl ether, so that hydroxyl is exposed out of a fluorophore, and the fluorescence intensity is enhanced (by more than 30 times). The fluorescent molecular probe has the advantages of stable photochemical properties, high fluorescence quantum yield, low price and the like, specifically recognizes hydrogen sulfide, is not interfered by ions such as Na<+>, Ca<2+>, NO2<->, H2O2, ClO<->, HSO4<->, CN2H4S, HSO3<->, S2O5<2-> and S2O8<2->, has a linear detection range increased to 0-40 [mu] mmol/L, can be used for quantitative detection of high-concentration hydrogen sulfide in river water, rainwater, drinking water, drilling fluid, marsh liquid and the like, 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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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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