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Preparation method and application of fluorescent probe based on benzothiazole Schiff base

A technology of benzothiazoles and fluorescent probes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high cost, harsh reaction conditions, and poor sensitivity of zinc ion molecular fluorescent probes

Active Publication Date: 2021-05-18
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Fluorescent probes are one of the most powerful tools for detecting analytes, but most of the reported zinc ion molecular fluorescent probes have high costs, complex synthesis processes, harsh reaction conditions, weak anti-interference ability, long response time, and high sensitivity. Poor problems, which are greatly limited in practical applications

Method used

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  • Preparation method and application of fluorescent probe based on benzothiazole Schiff base
  • Preparation method and application of fluorescent probe based on benzothiazole Schiff base
  • Preparation method and application of fluorescent probe based on benzothiazole Schiff base

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Embodiment 1

[0034] Synthesis of compound a: 2-aminothiophenol (2g, 16.1mmol) and 2-hydroxy-5-methylbenzaldehyde (2.45g, 16.1mmol) were added to a round-bottomed flask containing 20mL of anhydrous methanol, Add I to the solution 2 (2.04g, 8.05mmol), the mixture was heated to reflux for 4h under the protection of nitrogen. After the reaction was completed, it was cooled to room temperature, and a yellow solid precipitated out. The solid was collected, filtered with a Buchner funnel and washed with cold methanol. It was further dried in vacuo to obtain a pale yellow solid, namely compound a (1.63 g, 42.1%). The characterization results are as follows: 1 H NMR (600MHz, CDCl 3 )δ12.21(s,1H),7.92(d,J=8.2Hz,1H),7.84(d,J=8.0Hz,1H),7.54–7.43(m,2H),7.34(t,J=7.2 Hz, 1H), 7.19 (d, J=8.4Hz, 1H), 7.13 (d, J=8.4Hz, 1H), 2.29 (s, 3H).

[0035] Synthesis of compound b: Compound a (1.40g, 5.82mmol), hexamethylenetetramine (1.22g, 8.73mmol) were added to a round-bottomed flask containing 8mL trifluoroa...

Embodiment 2

[0038] Probe molecule with Zn 2+ UV absorption spectrum of concentration change

[0039] To test the probe molecules for different concentrations of Zn 2+ Under the same experimental conditions, a buffer solution of 1mL absolute ethanol and Tris-HCl (CH 3 CH 2 OH:Tris-HCl=3:2, V / V, 20mmol, pH=7.4) was added to 10μL probe molecule stock solution (1mmol / L) for Zn 2+ UV titration experiment, and test its UV absorption spectrum ( figure 1 ). Depend on figure 1 It can be seen that adding Zn 2+ Afterwards, a new absorption peak appeared at 421nm for the probe molecule, and as the concentration of zinc ions in the solution gradually increased, the absorption peak at 421nm gradually increased, and at the same time, the absorption peak at 363nm for the probe molecule red-shifted to 373nm. An isoabsorptive point appears at 383nm.

Embodiment 3

[0041] Probe molecules and Zn 2+ Fluorescence spectrum research before and after the action

[0042] For testing probe molecules with Zn 2+ Fluorescence spectra before and after the action, under the same experimental conditions, to 1mL absolute ethanol and Tris-HCl buffer solution (CH 3 CH 2 OH:Tris-HCl=3:2, V / V, 20mmol, pH=7.4), add 1μL probe molecule stock solution (1mmol / L), then drop 1μL different metal ion stock solution (10mmol / L), test Its fluorescence spectrum ( figure 2 ). Depend on figure 2 It can be seen that only adding Zn to the probe molecule solution 2+ After that, the emission peak at 480nm was significantly enhanced, accompanied by an obvious fluorescence color change from yellow to blue, indicating that the probe molecule could selectively detect zinc ions.

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Abstract

The invention discloses a preparation method and application of a fluorescent probe based on benzothiazole Schiff base, belonging to the technical field of fluorescent probes for metal ion detection. The molecular formula of the fluorescent probe is C34H31N5O2S2. The preparation method comprises the following steps: (1) subjecting 2-hydroxy-5-methylbenzaldehyde with 2-aminothiophenol to reacting to obtain a compound a; (2) carrying out the Darff reaction on the compound a and hexamethylenetetramine to generate a compound b; and (3) carrying out a condensation reaction on the compound b and diethylenetriamine to obtain a probe molecule L. The probe molecule reacts with zinc ions in a solution containing both absolute ethyl alcohol and Tris-HCl in a ratio of 3: 2, and the concentration of the zinc ions can be detected by utilizing the change of fluorescence intensity. The probe disclosed by the invention is simple and convenient to synthesize, mild in reaction conditions and high in selectivity and sensitivity to zinc ions, the response range of the probe is 0-8.00 [mu]M, and the detection limit of the probe is 60.4 nM. In addition, through a laser confocal scanning microtechnique, the novel fluorescent probe is successfully applied to detection of zinc ions in cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes for metal ion detection, and in particular relates to a preparation method and application of a benzothiazole-based Schiff base fluorescent probe. Background technique [0002] Zinc is an important trace element required by living organisms. It exists in the form of divalent cations. It is the second most abundant metal element after iron in the human body. It plays a vital role in various life activities of living organisms. It plays a major role in neurotransmission, gene expression, cellular metabolism, and synthesis of DNA and RNA. However, due to anthropogenic increases, zinc concentrations are constantly rising, and most zinc comes from industrial activities such as mining, coal, waste burning, and steel processing. Excessive zinc ions will not only pollute the environment, but also in terms of human health, the imbalance of zinc ions has caused many mental diseases, including Al...

Claims

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Application Information

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IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/6428G01N21/6486G01N21/643C09K2211/1037C09K2211/1014G01N2021/6439
Inventor 宋丽雪王丽韩辉
Owner SHANXI UNIV
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