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Coumarin-benzothiazolyl hydrazone compound, preparation method and application thereof

A technology of benzothiazolyl hydrazone and coumarin, which is applied in chemical instruments and methods, organic chemistry, and analysis through chemical reactions of materials, can solve the problems of expensive and cumbersome pretreatment, and achieve strong anti-interference The effect of ability, good application potential

Pending Publication Date: 2019-09-13
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the detection sensitivity of these detection methods is very high, the detection process requires very sophisticated and expensive experimental instruments and tedious pretreatment, etc.

Method used

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  • Coumarin-benzothiazolyl hydrazone compound, preparation method and application thereof
  • Coumarin-benzothiazolyl hydrazone compound, preparation method and application thereof
  • Coumarin-benzothiazolyl hydrazone compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of compound CTS

[0035] Weigh 2.45g (10mmoL) 3-formyl-7-N, N-diethylaminocoumarin and 1.65g (10mmoL) 2-hydrazinobenzothiazole respectively and dissolve them in 10mL absolute ethanol, stir to make Fully dissolve, add 0.5mL acetic acid as a catalyst, heat up to 75°C and reflux for 6h, filter the reaction solution after cooling, wash, dry, recrystallize from absolute ethanol, and obtain 2.50g of a yellow solid after drying, which is the target product, with a yield of 70.4 %.

[0036] FT-IR (KBr, cm -1 ): 3434.32 (-N-H), 2931, 2872 (-CH 3 ,-CH2 ), 1727(-C=O), 1624(-C=N-), 1602(-Ar), 1349(-C-H), 1131(-C-N), 638(-N-H).

[0037] 1 H NMR (400MHz, DMSO-d 6 ): δ(ppm)8.24(s,1H),8.14(s,1H),7.78(d,1H,J=8.0Hz),7.64(d,1H,J=8.0Hz),7.45(d,1H) ,7.30(t,1H),7.13(t,1H),6.77(d,1H,),6.59(s,1H),3.42(m,4H),1.15(t,6H).MS-ESI: m / z[M+H] + ,393.26 for C 21 h 20 N 4 o 2 S.

Embodiment 2

[0038] Embodiment 2: the ultraviolet-visible absorption spectrometry of compound CTS

[0039] Accurately weigh 3.9 mg of compound CTS, dissolve and prepare a concentration of 1.0×10 -2 mol / L acetonitrile stock solution; dilute the stock solution to a concentration of 1.0×10 with a mixture of acetonitrile and water at a volume ratio of 7:3 -5 mol / L of the solution to be tested. Take 3mL concentration as 1.0×10 -5 mol / L of the solution to be tested in a quartz cuvette (the thickness of the quartz cuvette is 1cm), and then add 3 μL of the solution at a concentration of 1.0×10 -2 mol / L of various metal ions (Na + , K + , Ag + , Ca 2+ , Mg 2+ , Pb 2+ , Li + , Al 3 + , Zn 2+ , Cd 2+ , Cr 3+ , Cu 2+ , Ni 2+ ,Co 2+ , Fe 3+ , Hg 2+ ) aqueous solution, shake well, and measure the UV-Vis absorption spectrum of the solution after 1 minute (see accompanying drawing figure 1 ). Before adding metal ions, the UV-Vis absorption spectrum of compound CTS showed an obvious ab...

Embodiment 3

[0040] Embodiment 3: the determination of the ultraviolet-visible absorption spectrum titration experiment and detection limit of compound CTS

[0041] Take 3mL concentration as 1.0×10 -5 mol / L of the solution to be tested is placed in a quartz cuvette, and the concentration is 1.0×10 -3 mol / L Cu 2+ Ionic aqueous solution, measure the ultraviolet-visible absorption spectrum of solution after shaking up (as accompanying drawing figure 2 shown). With Cu 2+ With the addition of ions, the absorbance of compound CTS at 459nm gradually weakens and blue-shifts to 450nm, and an obvious equivalence point appears at 450nm, indicating that compound CTS can with Cu 2+ ions form stable complexes, Cu 2+ ions at 1.0 x 10 -6 ~1.6×10 - 5 In the range of mol / L, Cu 2+ There is a good linear relationship between the ion concentration and the change of absorbance at 450nm (R 2 =0.98), through calculation, the compound CTS effect on Cu 2+ The detection limit of ions is 2.40×10 -6 mol / ...

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Abstract

The invention discloses a coumarin-benzothiazolyl hydrazone compound, a preparation method and application thereof. Specifically, the structural formula of the coumarin-benzothiazolyl hydrazone compound is shown as the specification. The hydrazone fluorescent probe compound provided by the invention has multifunctionality, also can realize identification and quantitative detection of Cu<2+> ions by visible spectrophotometry and fluorescent spectrometry, and has good anti-interference performance, high selectivity and sensitivity in the presence of other ions.

Description

technical field [0001] The invention relates to a coumarin-benzothiazolyl hydrazone compound and its preparation method and application, which belong to metal Cu 2+ Fields of ion detection and fluorescent molecular probes. Background technique [0002] Metal ions widely exist in our living environment, play an important role in the life system, and are closely related to human health. Some metal ions can enter the living body through various channels and accumulate in the living body, hindering the normal functioning of the living body. Therefore, it is very important to detect the content of various metal ions in the environment and the human body. [0003] The content of copper ions in cells is second only to aluminum and iron. It is an essential trace metal element in living organisms. Copper has a variable valence state and participates in a series of processes such as electron transfer and redox in living organisms; in the environment Too much copper will lead to seri...

Claims

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Application Information

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IPC IPC(8): C07D417/12C09K11/06G01N21/64G01N21/78
CPCC07D417/12C09K11/06G01N21/78G01N21/6428C09K2211/1088C09K2211/1037
Inventor 朱维菊徐培培刘校南方敏李村
Owner ANHUI UNIVERSITY
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