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Cyanide ion sensor molecule as well as synthesis and application thereof

A sensor and molecular technology, applied in the fields of chemical synthesis and anion detection, to achieve the effect of novel structure, good fluorescence performance and high sensitivity

Inactive Publication Date: 2018-05-04
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, if these two functional groups are combined into the same molecule, it is expected to obtain a fluorescent sensor with excellent performance, but such a molecule combining the Schiff base structure and the naphthalimide structure has rarely been reported.

Method used

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  • Cyanide ion sensor molecule as well as synthesis and application thereof
  • Cyanide ion sensor molecule as well as synthesis and application thereof
  • Cyanide ion sensor molecule as well as synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, the synthesis of sensor molecule HB1

[0037] (1) Synthesis of intermediate M: Weigh 1.98g (0.01mol) of 1,8-naphthalene dicarboxylic anhydride and 2.16g (0.01mol) of p-phenylenediamine, put them in a 50 mL round bottom flask, add 30mL of DMF, and Reflux at 135~140°C for 22~24 hours to form a brick-red precipitate; then recrystallize with water and DMF, and filter with suction to obtain the intermediate M——1,8-naphthalimide functionalized with 4-aminophenyl Derivatives, yield: 97%.

[0038] (2) Synthesis of sensor molecule HB1: Weigh 2.86g (0.01mol) of intermediate M and 1.93g (0.01mol) of 4-diethylaminosalicylaldehyde into a 50 mL round bottom flask, add 20 mL of Water ethanol and two drops of acetic acid (the catalyst is about 1% of the total substance), reflux at 80~85°C for 18~20 hours to form a brown precipitate; filter with suction and wash 2~3 times with hot absolute ethanol , and dried to obtain the sensor molecule HB1 with a yield of 78%.

[003...

Embodiment 2

[0041] Embodiment 2, solution detection CN -

[0042] Configure HB1 with DMSO as 2×10 -3 moL -1 The solution is in a 25mL colorimetric tube. Take 10 5mL colorimetric tubes, pipette 0.5mL of the prepared HB1 solution (the solution has weak fluorescence) into the 10 colorimetric tubes respectively; add F to the 10 colorimetric tubes respectively - , Cl - , Br - , I - , AcO - , H 2 PO 4 - , HSO 4 - , ClO 4 - , CN - and SCN - Aqueous solution (0.01mol L -1 ) 0.5mL, shake it to make it mix evenly (- ; If the fluorescence intensity of the HB1 solution does not change significantly, it means that other anions are added.

Embodiment 3

[0043] Embodiment 3, CN - Test paper and application

[0044] Several treated filter papers (3 × 1.5 cm 2 ) soaked in DMSO / HB1 2 O (8: 2 v / v) solution for 2 hours, take it out and dry it to make a test paper for detecting CN - . CN - Detection: drop anion F on the test paper respectively - , Cl - , Br - , I - , AcO - , H 2 PO 4 - , HSO 4 - , ClO 4 - , CN - and SCN - The aqueous solution of the test paper, if the fluorescence of the detection test paper turns blue under the irradiation of a 365 nm ultraviolet lamp, it means that what is added dropwise is CN - Solution; if the fluorescence of the test paper does not change under the irradiation of 365 nm ultraviolet lamp, it means that the cheap one is not CN - solution. In addition, it should be noted that the manufacturing process of the test paper loaded with HB1 is simple and the cost is extremely low. - After the action, it shows blue fluorescence under the irradiation of a 365 nm ultraviolet lamp. This...

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Abstract

The invention discloses a cyanide ion sensor molecule which is a novel sensor molecule HB1, is prepared by condensing a 4-aminophenyl functionalized 1,8-naphthalimide derivative with 4-lignocaine salicylaldehyde in a synthesis manner, and is of a naphthalimide structure and a Schiff base structure. Fluorescence detection on CN- in a DMSO (Dimethyl Sulfoxide) system of which the water content is 20-25% can be implemented. When solutions of F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4-, ClO4, CN- and SCN- are respectively put into an HB1 solution, results show that the fluorescence intensity of the HB1solution is remarkably enhanced only with addition of CN-, and the fluorescence of the HB1 solution is not conspicuously affected by addition of other negative ions. Anti-interference experiment results show that the recognition process is not interfered by other negative ions. The lowermost detection limit of HB1 to CN- recognition is up to 6.30*10<-8>M.

Description

technical field [0001] The present invention relates to a sensor molecule of cyanide ion, in particular to a sensor molecule based on the condensation of 4-aminophenyl functionalized 1,8-naphthalimide derivatives and 4-diethylaminosalicylaldehyde and its synthesis, the present invention also relates to the specific application of the cyanide ion sensor molecule, which belongs to the technical field of chemical synthesis and the technical field of anion detection. Background technique [0002] Cyanide is widely used in metallurgy, tanning, electroplating and other chemical processes, and plays an important role in industrial production. However, cyanide is highly toxic and easily absorbed by the human body, and can enter the human body through the mouth, respiratory tract or skin. When cyanide enters the stomach, under the dissociation of gastric acid, it can be immediately hydrolyzed into hydrocyanic acid and absorbed. After the substance enters the blood circulation, the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/643
Inventor 张有明韩冰冰毛鹏鹏陈进发林奇姚虹魏太保
Owner NORTHWEST NORMAL UNIVERSITY