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Azine-based CN-sensor molecule and synthesis and application thereof

A sensor and molecular technology, applied in the fields of chemical synthesis and anion detection

Inactive Publication Date: 2017-08-25
LANZHOU JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But no azine-based CN − Reports on sensor molecules

Method used

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  • Azine-based CN-sensor molecule and synthesis and application thereof
  • Azine-based CN-sensor molecule and synthesis and application thereof
  • Azine-based CN-sensor molecule and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1, the synthesis of sensor PX

[0038] Weigh (0.236g, 1.5mmol) quinoline-2-carbaldehyde and (0.204g, 1.5mmol) salicylaldehyde hydrazone respectively, dissolve them into a 50ml round bottom flask with 20ml DMF, add 0.3ml of glacial acetic acid as a catalyst, Heated to reflux at 85°C for 5 h, cooled to room temperature, added 5 ml of distilled water, a large amount of yellow precipitates precipitated, filtered, dried, and then recrystallized with DMF, after drying, the target product PX was obtained with a yield of 76%.

[0039] Color: yellow; Melting point: 164-166°C; 1 H-NMR (DMSO- d 6 , 400 MHz, ppm) δ: 11.07 (s,1H), 9.03 (s, 1H), 8.75 (s, 1H), 8.48(t, J=8.62 Hz, 1H), 8.22 (dd, J=8.33 Hz, 1H), 8.09 (m, 1H), 8.04(t, J=8.33Hz, 1H), 7.82(t, J=6.45 Hz 1H), 7.73(t, J=7.45 Hz, 1H), 7.67(t, J =6.97Hz, 1H), 7.41(t, J=7.24 Hz, 1H), 6.97(dd, J=7.99Hz, 2H). 13 C-NMR (DMSO- d 6 , 100 MHz, PPM) Δ: 164.39, 162.47, 157.30, 153.25,147.96, 137.41, 134.01, 131.43, 130....

Embodiment 2

[0040] Embodiment 2, CN － solution detection

[0041] Take 10 10 ml colorimetric tubes, add 0.5ml PX DMSO solution (2×10 -4 mol / L), and then add 0.5 ml anion (F − , Cl − , Br − , I − , AcO − , H 2 PO 4 − , HSO 4 − , ClO 4 − , SCN − and CN − ) in DMSO (10 -2 mol / L), if the color of the PX solution in the colorimetric tube changes from colorless to yellow, and under the ultraviolet light, the color of the PX solution in the colorimetric tube obviously changes from colorless to green, indicating that CN − , if the color of the PX solution in the colorimetric tube does not change significantly, and the fluorescence intensity of the PX solution does not change significantly under the ultraviolet light, it means that the addition of CN is not − .

Embodiment 3

[0042] Embodiment 3, CN － Production and application of test paper

[0043] Prepare PX with DMSO to 0.01 mol L −1 solution, take a piece of filter paper and cut it into two pieces with a length of about 3cm and a width of about 1cm, soak them in the DMSO solution of PX for 10 minutes, and then take them out to dry. The above filter paper was observed under ultraviolet light, no fluorescence was found on the filter paper.

[0044] Drop anion (F − , Cl − , Br − , I − , AcO − , H 2 PO 4 − , HSO 4 − , ClO 4 − , SCN − and CN − ) DMSO solution on the filter paper, if the color of the filter paper changes from colorless to yellow, and the color of the filter paper changes to green under the ultraviolet light, it means that the CN − , if the color of the filter paper does not change significantly under visible light and ultraviolet light, it means that other anions are added dropwise.

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Abstract

The invention provides an azine-based CN-sensor molecule. The synthetic method comprises the following steps: by taking DMF (Dimethyl Formamide) as a solvent and taking glacial acetic acid as a catalyst, refluxing quinoline-2-formaldehyde and salicylaldehyde hydrazone at the temperature of 80-85 DEG C for 5-5.5 hours according to a molar ratio of 1:1 to 1:1.2, cooling to room temperature, separating out a yellow precipitate by using distilled water, filtering, recrystallizing by using the DMF, and drying, thereby obtaining the product. The sensor molecule can specifically and selectively identify CN- in a DMSO-H2O mixed system, has extremely high sensitivity and is not influenced by negation ions, and the lowest fluorescent detection limit can reach 0.45mu M. In addition, test paper loaded with the sensor molecule is made, so that the CN- in a water-containing system can be conveniently detected. The sensor molecule designed and synthesized in the invention is cheap and readily available in synthetic raw materials, simple in process and low in cost and has wide prospects in the actual application of the CN-.

Description

technical field [0001] The present invention relates to a CN − Sensor molecules; especially related to an azine-based CN − The synthetic method of sensor molecule; The present invention also relates to this CN simultaneously − Sensor molecules in DMSO-H 2 Identify CN in O system − The application of the invention belongs to the field of chemical synthesis and the technical field of anion detection. Background technique [0002] Anions play an important role in industrial production and metabolism of organisms, so the research on anion sensors has attracted more and more attention. CN − As the most toxic anion, it can seriously affect the functions of blood vessels, vision, and central nervous system of the human body. According to the World Health Organization, CN − The maximum concentration in drinking water should not exceed 1.9µM, but because a large amount of NaCN is needed in industrial production such as metallurgy, synthetic resin, and electroplating, it has ca...

Claims

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Application Information

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IPC IPC(8): C07D215/12C09K11/06G01N21/33G01N21/64
CPCC07D215/12C09K11/06C09K2211/1029G01N21/33G01N21/6428G01N2021/6443
Inventor 胡京汉裴鹏祥倪鹏伟孙优龙辰
Owner LANZHOU JIAOTONG UNIV
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