A kind of potassium ion-sensitive anionic self-assembly functional material and its preparation method

A technology of functional materials and anions, which is applied in the field of anionic self-assembly functional materials and preparation, can solve problems such as disturbing and destroying the normal operation of life systems, and achieve broad application prospects and good small molecule loading activity effects

Inactive Publication Date: 2019-05-14
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of potassium ion-sensitive anionic self-assembly functional material and its preparation method
  • A kind of potassium ion-sensitive anionic self-assembly functional material and its preparation method
  • A kind of potassium ion-sensitive anionic self-assembly functional material and its preparation method

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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 anionic self-assembly functional material is obtained by using dibenzo-18-crown-6 functionalized biurea ligand L to coordinate with a phosphate anion; the dibenzo-18-crown- 6 The functionalized diurea ligand L is the reaction of (trans) diaminophenyl-18-crown-6 molecule with 2-nitrophenylisocyanate to generate intermediate L a , via palladium carbon catalyst (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 4-nitrophenyl isocyanate; 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 met...

Embodiment 2

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

[0034] Dissolve 2-nitrophenylisocyanate (0.43g, 2.63mmol) in 15ml of toluene, pour into a reaction flask and heat to 40-50°C; mmol) was suspended in 30mlTHF, slowly dropped into the hot solution of 2-nitrophenyl isocyanate, heated and stirred for 1h; an orange solid was precipitated, and more solids appeared after adding ether, and stood for a period of time; suction filtered, washed with ether to obtain 0.90 g product; 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 palladium carbon catalyst (Pd / C), add in the reaction bottle; Use 100mlTHF, 1.5ml hydrazine hydrate, reflux 3h; Reaction liquid is cooled, sand core funnel is covered with diatomaceous earth suction filtration, with (45+15+15) mlDMF dissolved the product in the filter cake, and filtered it 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 filtered, and washed with ether to obtain 1.38g of the product; Product L b Yield 93%.

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Abstract

A potassium ion-sensitive anionic self-assembly functional material and a preparation method belong to the field of functional materials. The present invention has produced a kind of dibenzo-18-crown-6 functionalized double diurea anion acceptor, through the hydrogen bond self-assembly (anion coordination) of its diurea group and phosphate anion, obtained A triple-helix molecular cage-like functional material that is sensitive to potassium ions and has a nanoscale cavity; in the absence of potassium ions, the molecular cage can enclose tetraethyl quaternary ammonium salt molecules, and after adding potassium ions, The dibenzo-18-crown-6 functional group of this molecular cage will complex potassium ions, thereby producing an electrostatic repulsive effect on the enclosed quaternary ammonium salt molecules and releasing them. The anionic self-assembled functional material prepared by the present invention has good small molecule loading activity, and can generate intelligent responses to potassium ions in the environment to release loaded molecules. The material is useful in the fields of drug loading, molecular transport, and controllable release Broad application prospects.

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 Patents(China)
IPC IPC(8): C07D323/00
CPCC07D323/00
Inventor 贾传东黄喆
Owner NORTHWEST UNIV
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