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Indole semicyanine fluorescent probe, preparation method and application in cyanide ion detection

A fluorescent probe, indole hemicyanine technology, applied in the fields of chemical synthesis and analysis and detection, can solve the problems of expensive instruments, high detection limit, long time consumption, etc., and achieve the effects of rapid reaction, short synthesis steps and high yield

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

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Problems solved by technology

These methods usually have the disadvantages of time-consuming, expensive instruments, and high detection limits.

Method used

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  • Indole semicyanine fluorescent probe, preparation method and application in cyanide ion detection
  • Indole semicyanine fluorescent probe, preparation method and application in cyanide ion detection
  • Indole semicyanine fluorescent probe, preparation method and application in cyanide ion detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of 2-(2-(2-chloro-7-diethylaminoquinolin-3-yl)vinyl-N,3,3-trimethyl-3H-indole (QIE) (stirred reflux method).

[0046]Add 0.33g (1.2mmol) 7-N,N-diethylamino-2-chloro-3-quinoline formaldehyde, 0.42g (1.4mmol) 1,2,3,3-tetramethyl- 3H-iodine indole salt, add 5mL of n-butanol dropwise, stir to dissolve the solid, add 5 drops of pyridine, stir and reflux for 3h, TLC traces that the reaction is complete, stop stirring, cool to room temperature, filter with suction, and wash the filter cake with cold ethanol ,dry. Silica gel column chromatography, eluting with petroleum ether and ethyl acetate (100 / 3-100, v / v), gave 0.42 g of purple-black solid QIE, with a yield of 83.73%, m.p.: 220.8-222.3°C. IR(KBr), ν / cm -1 : 1588, 1515. 1 H NMR (400MHz. DMSO, δppm), 9.20(s, 1H), 8.49(d, J=16.1Hz, 1H), 7.91~7.87(3H), 7.75~7.61(3H), 7.40(dd, J=9.3 ,2.2Hz,1H), 6.95(d,J=1.8Hz,1H), 4.16(s,3H), 3.58(q,J=6.8Hz,4H), 1.79(s,6H), 1.21(t,, J=7.0Hz, 6H). ESI-MS: 418.24(M).

Embodiment 2

[0048] Preparation of (2-(2-chloro-7-diethylaminoquinolin-3-yl)vinyl-N,3,3-trimethyl-3H-indole (QIE) (microwave reaction method).

[0049] Add 0.33g (1.2mmol) 7-N,N-diethyl-2-chloro-3-quinoline formaldehyde to the test tube, add 0.44g (1.4mmol) 1,2,3,4-tetramethylindole , adding 5 drops of pyridine, reacting in microwave for 20 minutes, cooling, adding ethanol, stirring, filtering to obtain a purple-black solid. Ethanol was added to the solid, stirred at room temperature for 10 hours, suction filtered, and the operation was repeated three times to obtain 0.46 g of a purple-black pure product with a yield of 91.71%. The characterization data are as in Example 1.

Embodiment 3

[0051] (1) Preparation of test solution:

[0052] In a 2mL sample bottle, add 1.0mL double distilled water, then add 1×10 -2 mol / L currently configured cyanide ion (CN - ) standard solution (20μL, 10eq), then add 1.0mL methanol, mix well; finally add 20μL QIE DMF solution (1×10 -3 mol / L), and mix again. After standing for 10 minutes, measure the ultraviolet absorption spectrum and fluorescence emission spectrum (416nm is the excitation wavelength). The above operation, without adding anion solution, is the preparation of blank test solution. Measure the UV absorption spectrum and fluorescence emission spectrum.

[0053] (2) Ultraviolet spectrum and fluorescence spectrum test:

[0054] The blank test solution of QIE has a strong maximum absorption peak at 555nm; when there is cyanide ion, the absorption intensity at 555nm is obviously weakened, see image 3 . The blank test solution of probe QIE has no fluorescence emission peak at 496nm, after adding cyanide ion, the fl...

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Abstract

The invention provides an indole semicyanine fluorescent probe, a preparation method and its application in the detection of cyanide ions. The probe specifically involved is 2‑(2‑(2‑chloro‑7‑diethylaminoquinolin‑3‑yl) vinyl‑N,3,3‑trimethyl‑ 3H‑ Indole (QIE). It is based on 2-chloro-7-diethylaminoquinoline-3-formaldehyde and N,2,3,3-tetramethyl- 3H‑ Indole is prepared by condensation of raw materials. After the cyanide ions reacted with QIE, the naked eye could see that the solution changed from purple to colorless, and under a 365 nm ultraviolet light, the solution changed from dark purple fluorescence to bright yellow-green fluorescence. The minimum detection limit of cyanide ion by UV-Vis spectrophotometry is 1.05×10 ‑6 mol / L, the minimum detection limit of cyanide ion detected by fluorescence spectrophotometry is 4.16×10 ‑8 mol / L. The invention can quantitatively and qualitatively detect micro / trace cyanide ions in samples from different sources by means of dual channels of ultraviolet-visible spectrophotometry and fluorescence spectrophotometry.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and analysis and detection, and in particular relates to a probe for detecting cyanide ions, a preparation method thereof and an application in detecting cyanide ions. Background technique [0002] The carbon atom and nitrogen atom in cyanide are connected by a triple bond, which is linear and has high stability and strong electron-withdrawing ability. At the same time, cyanide ion has a strong complexing ability for metal ions, so cyanide is It has a wide range of applications in the fields of chemistry, medicine, life science, industrial production, food analysis and environmental monitoring. For example, it is used in chemical fields such as synthetic fibers, resins, medicines, pesticides, fertilizers, dyes, and pigments; it is used in industrial fields such as gold mining, electroforging and electroplating, metal smelting, electronics, and instrumentation. Not only that, cassava, b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/06C09K11/06G01N21/64
CPCC07D401/06C09K11/06C09K2211/1029G01N21/6428
Inventor 但飞君曾晓燕马尚虎唐倩兰海闯李玉杰廖全斌
Owner CHINA THREE GORGES UNIV
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