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Potassium ion-sensitive anion self-assembly functional material and preparation method thereof

A technology of functional materials and anions, which is applied in the field of anionic self-assembly functional materials and preparations, can solve the problems of destroying the normal operation of life systems, disturbances, etc., and achieve the effect of good small molecule loading activity and broad application prospects

Inactive Publication Date: 2019-01-15
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, whether it is heavy metal ions or the corresponding stimuli, they usually disturb or even destroy the normal operation of living systems. Therefore, to realize potential biological applications such as drug release in human organs, it is necessary to develop new, bio-friendly smart responsive materials.

Method used

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  • Potassium ion-sensitive anion self-assembly functional material and preparation method thereof
  • Potassium ion-sensitive anion self-assembly functional material and preparation method thereof
  • Potassium ion-sensitive anion self-assembly functional material and preparation method thereof

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Effect test

Embodiment 1

[0026] A potassium ion sensitive anion self-assembly functional material, the anion self-assembly functional material molecular formula is: (TBA) 6 [L 3 (PO 4 ) 2 ]; the anion self-assembly functional material is obtained by using the dibenzo-18-crown-6 functionalized biurea ligand L to coordinate with the phosphate anion; the dibenzo-18-crown-6 function The converted diurea ligand L is the reaction of (trans) diaminophenyl 18-crown-6 molecule with 2-nitroisocyanate to generate intermediate L a , via Pd / C, hydrazine hydrate to intermediate L a Reductive hydrogenation gives intermediate L b , and then intermediate L b It is obtained by reacting with tetranitroisocyanate; the phosphate anion is tetrabutylammonium phosphate, and the molecular formula is (TBA) 3 PO 4 ; The potassium ion-sensitive anion self-assembly functional material is self-assembled by mixing L and tetrabutylammonium phosphate in a ratio of 3:2.

[0027] The synthesis method of the dibenzo-18-crown-6 f...

Embodiment 2

[0033] Intermediate L a The synthesis method is as follows:

[0034] Dissolve o-nitroisocyanate (0.43g, 2.63mmol) in 15ml of toluene, pour into a reaction flask and heat to 40-50°C; Suspended in 30ml of THF, slowly dripped into the hot solution of o-nitroisocyanate, heated and stirred for 1 hour; an orange solid precipitated, and more solids appeared after adding ether, and stood for a while; suction filtered, washed with ether to obtain 0.90g of the product; The resulting product L a Yield 97%.

Embodiment 3

[0036] Intermediate L b The synthesis method is as follows:

[0037] Under the condition of nitrogen protection, the L a (1.60g, 2.23mmol), 0.16g Pd / C, added to the reaction flask; with 100mlTHF, 1.5ml hydrazine hydrate, refluxed for 3h; the reaction solution was cooled, and the sand core funnel was covered with diatomaceous earth and suction filtered, with (45+15+ 15) ml DMF dissolved the product in the filter cake, and suction filtered through diatomaceous earth; the mother liquor was rotary evaporated to a small amount of solvent, and a large amount of ether was added to precipitate a white solid; suction filtration, ether washing, obtained 1.38g product; the obtained product L b Yield 93%.

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Abstract

The invention relates to a potassium ion-sensitive anion self-assembly functional material and a preparation method thereof, and belongs to the field of functional materials. A dibenzo-18-crown-6 functionalized dibiurea anion acceptor is prepared, a triple-helical molecular cage-like functional material having nano-cavity and sensitive to potassium ions is prepared by self-assembling effect (anioncoordination) of biurea groups and hydrogen bonds of phosphate anions. Under a condition without potassium ions, a molecular cage can be entrapped with tetraethyl quaternary ammonium salt molecules;while after the potassium ions are added, the dibenzo-18-crown-6 functional group of the molecular cage can be complexed with the potassium ions, and thus the electrostatic repulsion effect is produced to the entrapped quaternary ammonium salt molecules to release the entrapped quaternary ammonium salt molecules. The prepared anion self-assembly functional material has good small-molecular loadingactivity, and intelligent response to potassium ions in the environment can be generated and the loaded molecules are released. The material has broad application prospects in the fields of drug loading, molecular transmission, controllable release and the like.

Description

technical field [0001] The invention belongs to the field of functional materials, and specifically refers to a potassium ion-sensitive anion self-assembly functional material and a preparation method. Background technique [0002] In the living body, protein molecules selectively bind biologically active guest molecules through the holes formed by their self-assembly and folding to achieve important life functions such as immunity, signal transmission, and biocatalysis. Inspired by the cavity structure of proteins, since the 1970s, chemists have synthesized a large number of macrocyclic or cage-like artificial molecules with similar cavities, in order to deeply understand the working principle of proteins, and further imitate their functions and Intervention, to achieve applications in the fields of disease diagnosis and pharmaceutical research and development. The artificial receptors studied in the early stage mainly include molecular macrocycles represented by crown eth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D323/00
CPCC07D323/00
Inventor 贾传东黄喆
Owner NORTHWEST UNIV(CN)
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