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CN-121974905-A - Carbazole-thiazole Schiff base fluorescent probe and preparation method and application thereof

CN121974905ACN 121974905 ACN121974905 ACN 121974905ACN-121974905-A

Abstract

The invention provides a carbazole-thiazole Schiff base fluorescent probe and a preparation method and application thereof, and belongs to the technical field of fluorescent probes. The preparation method comprises the following steps of mixing benzothiazole-2-formaldehyde solution and 3-amino-9-ethyl carbazole solution, and performing Schiff base condensation reaction to obtain the carbazole-thiazole Schiff base fluorescent probe. The preparation method is simple, the reaction condition is mild, the yield is high, the cost is low, the fluorescent probe can identify and detect mercury ions, ferric ions, aluminum ions and chromium ions with high selectivity and high sensitivity through fluorescence and color dual signals, the detection limit is low to the nanomole level, and the fluorescent probe has high sensitivity. After being combined with different target ions, the probe shows obvious color change and fluorescence enhancement under sunlight and ultraviolet light, can realize quick distinction by naked eyes, and has wide application prospects in the fields of environment monitoring, biological imaging, food safety detection and the like.

Inventors

  • YU LIANGMIN
  • DONG WENJIAN
  • GUO RUNXIN
  • LI XIA
  • JIANG XIAOHUI
  • YAN XUEFENG

Assignees

  • 中国海洋大学三亚海洋研究院
  • 中国海洋大学
  • 三亚海洋实验室

Dates

Publication Date
20260505
Application Date
20260128

Claims (9)

  1. 1. The carbazole-thiazole Schiff base fluorescent probe is characterized by having a structural formula as follows: 。
  2. 2. The method for preparing the carbazole-thiazole Schiff base fluorescent probe according to claim 1, which is characterized by comprising the following steps: And mixing benzothiazole-2-formaldehyde solution and 3-amino-9-ethyl carbazole solution, and performing Schiff base condensation reaction to obtain the carbazole-thiazole Schiff base fluorescent probe.
  3. 3. The preparation method of claim 2, wherein the benzothiazole-2-formaldehyde solution consists of benzothiazole-2-formaldehyde and an organic solvent, the 3-amino-9-ethylcarbazole solution consists of 3-amino-9-ethylcarbazole and the organic solvent, and the mass ratio of 3-amino-9-ethylcarbazole to benzothiazole-2-formaldehyde is 0.21-2.1:0.163-1.63.
  4. 4. A method according to claim 2 or 3, wherein the organic solvent independently comprises one or more of absolute ethanol, methanol, acetonitrile, isopropanol, N-dimethylformamide and N, N-dimethylacetamide.
  5. 5. The method according to claim 4, wherein the temperature of the schiff base condensation reaction is 25-90 ℃ and the time is 1-24 hours.
  6. 6. The use of the carbazole-thiazole schiff base fluorescent probe according to claim 1 for preparing a material for detecting metal ions.
  7. 7. The use according to claim 6, wherein the metal ion is one or more of mercury ion, ferric ion, aluminum ion and trivalent chromium ion.
  8. 8. The use according to claim 6 or 7, wherein the carbazole-thiazole schiff base fluorescent probe is dissolved in an organic solvent to obtain a fluorescent probe mother liquor, the fluorescent probe mother liquor is diluted with a methanol solution to obtain a fluorescent probe solution, and a sample to be tested containing metal ions is mixed with the fluorescent probe solution for detection.
  9. 9. The use according to claim 8, wherein the methanol solution has a volume fraction of 60-99% methanol, the fluorescent probe has a concentration of 5 x 10 -4 ~5×10 -3 mol/L in the fluorescent probe mother solution, and the fluorescent probe has a concentration of 1 x 10 -6 ~5×10 -4 mol/L in the fluorescent probe solution.

Description

Carbazole-thiazole Schiff base fluorescent probe and preparation method and application thereof Technical Field The invention relates to the technical field of fluorescent probes, in particular to a carbazole-thiazole Schiff base fluorescent probe and a preparation method and application thereof. Background A variety of metal ions play a vital role in environmental monitoring, life sciences and industrial processes. Among them, mercury ion (Hg 2+) is one of the most toxic heavy metal ions, and has high bioaccumulation and neurotoxicity. Ferric ion (Fe 3+) is used as a trace element necessary for human body, and the metabolic imbalance is related to various diseases. Although aluminum ion (Al 3+) is a light metal, its excessive exposure is closely related to neurodegenerative diseases and environmental acidification problems. Trivalent chromium ion (Cr 3+) is a trace element essential to human body, but its concentration needs to be strictly controlled. Therefore, a method capable of detecting the above-mentioned various metal ions rapidly, with high selectivity and high sensitivity is urgently required. The fluorescent probe method is favored because of the advantages of high sensitivity, simple operation, capability of realizing real-time in-situ detection and the like. The carbazole compound has a large conjugated system and a rigid plane, and is an excellent fluorophore. The thiazole ring and the multiple coordination sites formed by the thiazole ring and the Schiff base structure provide an ideal platform for selectively identifying metal ions. However, in the prior art, there are still limited reports on detection of four ions of Hg 2+、Fe3+、Al3+ and Cr 3+ that can be achieved with a single probe molecule. Most probes have the problems of selective crossing, complex synthesis route, high detection limit, poor sensitivity and the like. Therefore, the development of the fluorescent probe which has novel structure, simple synthesis and can simultaneously or selectively identify a plurality of key metal ions has important theoretical value and practical application significance. Disclosure of Invention The invention aims to provide a carbazole-thiazole Schiff base fluorescent probe and a preparation method and application thereof, aiming at the defects of the prior art, and the probe has the advantages of simple synthesis method, good stability and high selectivity and high sensitivity in detection of Hg 2+、Fe3+、Al3+ and Cr 3+. In order to achieve the above object, the present invention provides the following technical solutions: The invention provides a carbazole-thiazole Schiff base fluorescent probe, which has the structural formula as follows: 。 the invention also provides a preparation method of the carbazole-thiazole Schiff base fluorescent probe, which comprises the following steps: And mixing benzothiazole-2-formaldehyde solution and 3-amino-9-ethyl carbazole solution, and performing Schiff base condensation reaction to obtain the carbazole-thiazole Schiff base fluorescent probe. Preferably, the benzothiazole-2-formaldehyde solution consists of benzothiazole-2-formaldehyde and an organic solvent, the 3-amino-9-ethylcarbazole solution consists of 3-amino-9-ethylcarbazole and the organic solvent, and the mass ratio of the 3-amino-9-ethylcarbazole to the benzothiazole-2-formaldehyde is 0.21-2.1:0.163-1.63. Preferably, the organic solvent independently comprises one or more of absolute ethanol, methanol, acetonitrile, isopropanol, N-dimethylformamide and N, N-dimethylacetamide. Preferably, the temperature of the Schiff base condensation reaction is 25-90 ℃ and the time is 1-24 hours. The invention also provides application of the carbazole-thiazole Schiff base fluorescent probe in preparing a material for detecting metal ions. Preferably, the metal ion is one or more of mercury ion, ferric ion, aluminum ion and trivalent chromium ion. Preferably, the carbazole-thiazole Schiff base fluorescent probe is dissolved in an organic solvent to obtain a fluorescent probe mother solution, the fluorescent probe mother solution is diluted with a methanol solution to obtain a fluorescent probe solution, and a sample to be detected containing metal ions is mixed with the fluorescent probe solution for detection. Preferably, the volume fraction of methanol in the methanol solution is 60-99%, the concentration of the fluorescent probe in the fluorescent probe mother solution is 5X 10 -4~5×10-3 mol/L, and the concentration of the fluorescent probe in the fluorescent probe solution is 1X 10 -6~5×10-4 mol/L. The invention has the beneficial effects that: The carbazole-thiazole Schiff base fluorescent probe has the advantages of 1) simple synthesis, one-step condensation, mild condition, high yield and low cost, 2) one probe with multiple targets, namely, four ions of Hg 2+、Fe3+、Al3+、Cr3+ can be identified simultaneously or selectively, 3) double signal output, namely, specific ultraviolet absorption change and fluorescenc