M-benzenedicarbonyl thioureas derivative, preparation and application thereof as fluorinion identification receptor

A technology of isophthaloyl thiourea and isophthaloyl chloride, applied in the field of fluoride ion recognition receptors, can solve the problems of environmental pollution, solvent volatilization waste, flammability, etc.

Inactive Publication Date: 2009-07-22
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the conventional solvent method has simple equipment and easy operation, there are defects such as solvent volatilization, waste and flammability in the reaction, which may easily cause environmental pollution and potential safety hazards.

Method used

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  • M-benzenedicarbonyl thioureas derivative, preparation and application thereof as fluorinion identification receptor
  • M-benzenedicarbonyl thioureas derivative, preparation and application thereof as fluorinion identification receptor
  • M-benzenedicarbonyl thioureas derivative, preparation and application thereof as fluorinion identification receptor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1, the preparation method of isophthaloyl thiourea derivative 3a of the present invention: be that isophthaloyl dichloride and ammonium thiocyanate are joined in the mortar with the molar ratio of 1: 2.5, then add thiocyanic acid Polyethylene glycol-400 with an ammonium content of 2% was intermittently ground and reacted for 5 hours at room temperature to obtain isophthaloyl isothiocyanate; base aniline, reacted intermittently at room temperature for 6 hours to obtain a yellow precipitate; filtered, washed, and washed with DMF-C 2 h 5 OH-H 2 O (where DMF:C 2 h 5 OH:H 2 O (the molar ratio of O is 1:0.8:0.4) was recrystallized from a mixed solvent to obtain the isophthaloylthiourea derivative 3a with a yield of 72.4%.

Embodiment 2

[0064] Embodiment 2, the preparation method of isophthaloyl thiourea derivative 3b of the present invention: be that isophthaloyl dichloride and ammonium thiocyanate are joined in the mortar with the molar ratio of 1: 2.8, then add thiocyanic acid Polyethylene glycol-400 with an ammonium content of 3% was intermittently ground and reacted for 6 hours at room temperature to obtain isophthaloyl isothiocyanate; then add aniline with 2.2 times the amount of isophthaloyl chloride, Intermittent grinding reaction at room temperature for 24 hours, a pale yellow precipitate was obtained; filtered, washed, and washed with DMF-C 2 h 5 OH-H 2 O (where DMF:C 2 h 5 OH:H 2 O (the molar ratio of O is 1:1.0:0.5) was recrystallized from a mixed solvent to obtain the isophthaloylthiourea derivative 3b with a yield of 87.5%.

Embodiment 3

[0065] Embodiment 3, the preparation method of isophthaloyl thiourea derivative 3c of the present invention: be that isophthaloyl dichloride and ammonium thiocyanate are joined in the mortar with the molar ratio of 1: 3, then add thiocyanic acid Polyethylene glycol-400 with an ammonium content of 4% was ground intermittently for 7 hours at room temperature to obtain isophthaloyl isothiocyanate; then add 2.5 times the amount of isophthaloyl chloride Oxyaniline, reacted intermittently at room temperature for 48 hours to obtain a pale yellow precipitate; filtered, washed, and washed with DMF-C 2 h 5 OH-H 2 O (where DMF:C 2 h 5 OH:H 2 O (the molar ratio of O is 1:1.2:0.6) was recrystallized from a mixed solvent to obtain the isophthaloylthiourea derivative 3c with a yield of 84.2%.

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Abstract

The invention provides a kind of fluoride ion recognition acceptor isophthaloyl thiourea derivatives 3a, 3b, 3c and a phase transfer solvent-free grinding method preparation method thereof, which is to prepare isophthaloyl chloride and ammonium thiocyanate in a certain amount The proportion of the mixture was added to the mortar, and under the condition of phase transfer catalyst, the reaction was intermittently ground at room temperature for 5 to 7 hours to obtain isophthaloyl isothiocyanate; After 6 to 48 hours, a yellow or light yellow precipitate is obtained; filter, wash, and recrystallize with a mixed solvent of DMF-C2H5OH-H2O. The isophthaloylthiourea derivative receptors of the present invention have high recognition selectivity for fluoride ions: receptor 3a can use its obvious color change to identify fluoride ions with naked eyes; receptors 3a, 3b, and 3c can use Fluoride ion was identified by UV-Vis absorption spectrum and 1HNMR titration.

Description

technical field [0001] The invention relates to a class of isophthaloyl thiourea derivatives and a phase-transfer catalyzed solvent-free grinding preparation method of the derivatives, and also relates to the application of the derivatives as fluoride ion recognition acceptors. Background technique [0002] The interaction and mutual recognition between host and guest molecules, especially the interaction between host and guest with optical information response function, is one of the frontier topics in the field of supramolecular chemistry research. Molecular recognition is the process in which the subject selectively binds to the guest and produces a specific function. It is a necessary way to assemble high-level structures and the basis for studying the functions of assemblies. Anions play an important role in the metabolic process of organisms, and their transport inside and outside the cell membrane is completed under the control and recognition of corresponding binding...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C335/26G01N21/78G01N21/25
Inventor 魏太保魏薇张有明曹成
Owner NORTHWEST NORMAL UNIVERSITY
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