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CN-121991030-A - Hydrazine hydrate detection fluorescent probe based on 1, 8-naphthalimide derivative as matrix, and preparation method and application thereof

CN121991030ACN 121991030 ACN121991030 ACN 121991030ACN-121991030-A

Abstract

The invention discloses a hydrazine hydrate detection fluorescent probe NPB taking 1, 8-naphthalimide as a parent, and a preparation method and application thereof. The fluorescent probe uses 1, 8-naphthalimide as a fluorescent group, and the structure of the fluorescent probe is shown as follows. The invention constructs the fluorescent probe NPB based on the 1, 8-naphthalimide as a matrix through condensation reaction, and the probe has excellent selectivity and high sensitivity detection performance on hydrazine hydrate in solution. In addition, the probe NPB has stable structure, can be prepared into a test paper form, is suitable for rapid detection of trace hydrazine hydrate in water samples, foods and air, and can be successfully applied to detection of the hydrazine hydrate in a PK-15 active cell system due to low cytotoxicity. The fluorescent probe provided by the invention has the advantages of simple preparation method, easily obtained raw materials, solid powder, convenience in storage and good application and development prospects.

Inventors

  • XU HAIYAN
  • WANG SHENGZE
  • XU AIYU
  • TIAN YUAN

Assignees

  • 江苏科技大学

Dates

Publication Date
20260508
Application Date
20251217

Claims (10)

  1. 1. The hydrazine hydrate detection fluorescent probe NPB based on the 1, 8-naphthalimide derivative is used as a parent body, and is characterized in that the hydrazine hydrate detection fluorescent probe NPB takes the 1, 8-naphthalimide derivative as a fluorescent group, and the structure of the hydrazine hydrate detection fluorescent probe NPB is shown as the following formula I: 。
  2. 2. A method for preparing a hydrazine hydrate detection fluorescent probe NPB based on a1, 8-naphthalimide derivative as a matrix according to claim 1, comprising the steps of: Mixing N-butyl-6-bromonaphthalimide and 4-piperazine-1-benzaldehyde in an organic solvent under the protection of inert gas, heating and refluxing for reaction, performing reduced pressure distillation after the reaction is finished, sequentially washing, extracting, drying, performing reduced pressure distillation again to remove the solvent to obtain a crude product, and purifying the crude product by recrystallization to obtain a compound II; And (3) dissolving the compound II and barbituric acid in an organic solvent containing acetic acid, heating and stirring, cooling a reaction mixture after the reaction is finished, filtering and collecting solid, washing and airing the solid, and thus obtaining the target fluorescent probe.
  3. 3. The method for preparing the hydrazine hydrate detection fluorescent probe NPB based on the 1, 8-naphthalimide derivative as a matrix according to claim 1, wherein the synthetic route is preferably as follows: 。
  4. 4. The preparation method according to claim 2, wherein the N-butyl-6-bromonaphthalimide and 4-piperazine-1-benzaldehyde are dissolved in N, N-Dimethylformamide (DMF) according to a molar ratio of 1:1-1:2, and reflux reaction is carried out under nitrogen atmosphere. After the reaction, a part of the solvent was distilled off under reduced pressure, the reaction solution was washed with brine and extracted with dichloromethane, the combined organic phases were dried over anhydrous sodium sulfate, and concentrated again under reduced pressure to give a crude product, which was finally purified by chromatography to give compound II.
  5. 5. The preparation method according to claim 2, wherein the molar ratio of the compound II to barbituric acid is 1:1-1.5, acetic acid is added as a catalyst, the reaction is stirred at 80-100 ℃ for 5-6 h, the reaction solution is cooled and filtered, and the obtained solid is washed with ethanol and dried to obtain the fluorescent probe NPB.
  6. 6. Use of a hydrazine hydrate detection fluorescent probe NPB based on a1, 8-naphthalimide derivative as a parent according to claim 1 for detecting hydrazine hydrate.
  7. 7. The application of the hydrazine hydrate detection fluorescent probe NPB based on the 1, 8-naphthalimide derivative as a matrix, which is characterized by being applied to detection of trace hydrazine hydrate in water, soil and agricultural products.
  8. 8. The application of the detection test paper according to claim 6, wherein the detection test paper prepared by using the hydrazine hydrate detection fluorescent probe NPB based on the 1, 8-naphthalimide derivative as a parent is applied to the detection of hydrazine hydrate.
  9. 9. Use of a hydrazine hydrate detection fluorescent probe NPB based on a1, 8-naphthalimide derivative as a parent according to claim 1 for the preparation of a reagent for detecting hydrazine hydrate in an active cell system.
  10. 10. Use of a hydrazine hydrate detection fluorescent probe NPB based on a1, 8-naphthalimide derivative as a parent according to claim 1 for detecting hydrazine hydrate in plant rhizomes.

Description

Hydrazine hydrate detection fluorescent probe based on 1, 8-naphthalimide derivative as matrix, and preparation method and application thereof Technical Field The invention belongs to the technical field of fluorescent probes, and particularly relates to a hydrazine hydrate detection fluorescent probe based on a1, 8-naphthalimide derivative and barbituric acid as precursors, and a preparation method and application thereof. Background Inorganic contaminants are of great concern because of their chemical stability, toxicity and environmental durability. The hydrazine hydrate is used as a highly active and highly toxic inorganic compound, is widely applied in the fields of agriculture and chemical industry, and relates to a plurality of aspects such as rocket fuel, water treatment, drug synthesis and the like. However, hydrazine hydrate causes serious pollution and health problems in a wide use process due to its high volatility and toxicity. Either short-term high dose exposure or long-term low dose exposure may cause damage to organs such as the liver, kidneys, lungs, etc., and present a potential carcinogenic risk. The hydrazine hydrate in the environment has complex sources, high concentration and difficult biodegradation, so that the pollution problem is increasingly emphasized. Hydrazine not only constitutes a hazard to the environment, but also exhibits extremely high biotoxicity. Therefore, the method for detecting the hydrazine hydrate in real time, is simple and convenient, and can be used for detecting the hydrazine hydrate in real time, and has very important significance for ecological environment and human health. Currently, common analytical methods for detecting hydrazine hydrate include gas chromatography, electrochemical methods, spectrophotometry and the like, however, these techniques are generally long in time consumption, have certain requirements on professional ability of operators, and limit the practical application range thereof. In contrast, the fluorescent probe has the advantages of high sensitivity, simple and convenient operation, realization of real-time detection and the like, and has good application prospect. Although various fluorescent probes for detecting hydrazine hydrate are reported at present, most of the probes still have the problems of short emission wavelength, insufficient anti-interference capability and the like, which restrict the application of the probes in practical samples (J. Mol. Structure. 2025,1337,142208; curr. Anal. Chem. 2024,20,8). It is noted that near infrared probes with emission wavelengths between 600 and 900 nm are effective in reducing interference from biological autofluorescence probes. Therefore, developing near infrared fluorescent probes that combine high sensitivity, rapid response capability, and good biocompatibility has become an important challenge in the field at present. Disclosure of Invention Aiming at the problems existing in the prior art, the invention aims to provide a fluorescent probe for detecting hydrazine hydrate. The probe takes a1, 8-naphthalimide derivative as a matrix and barbituric acid as a specific reaction group, and aims to solve the problems of poor selectivity, slow response and the like in the prior detection technology. The fluorescent probe has the outstanding advantages of excellent hydrazine hydrate selectivity, quick response time, strong anti-interference capability and the like, and can realize the rapid and sensitive detection of trace hydrazine hydrate in environment and biological samples. The invention also provides a preparation method and application of the hydrazine hydrate detection fluorescent probe based on the 1, 8-naphthalimide derivative as a parent. The invention provides a hydrazine hydrate detection fluorescent probe NPB based on a1, 8-naphthalimide derivative as a parent, which is characterized in that the hydrazine hydrate detection fluorescent probe NPB takes the 1, 8-naphthalimide derivative as a fluorescent group, and the structure of the hydrazine hydrate detection fluorescent probe NPB is shown as the following formula I: 。 The preparation method of the hydrazine hydrate detection fluorescent probe NPB based on the 1, 8-naphthalimide derivative as a parent body comprises the following steps: Mixing N-butyl-6-bromonaphthalimide and 4-piperazine-1-benzaldehyde in an organic solvent under the protection of inert gas, heating and refluxing for reaction, performing reduced pressure distillation after the reaction is finished, sequentially washing, extracting, drying, performing reduced pressure distillation again to remove the solvent to obtain a crude product, and purifying the crude product by recrystallization to obtain a compound II; And (3) dissolving the compound II and barbituric acid in an acetic acid solution of an organic solvent, heating and stirring, cooling a reaction mixture after the reaction is finished, filtering and collecting solid, washing and airing the solid,