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Iminoguanidine functionalized water-soluble column[5]arene and its preparation method and application

An iminoguanidine, functionalized technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., to achieve the effects of high yield, good molecular planarity and stability, and cheap raw materials

Active Publication Date: 2022-02-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The report of pillar arenes opened a new chapter in supramolecular chemistry, and also brought new opportunities and challenges to the research of supramolecular chemistry

Method used

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  • Iminoguanidine functionalized water-soluble column[5]arene and its preparation method and application
  • Iminoguanidine functionalized water-soluble column[5]arene and its preparation method and application
  • Iminoguanidine functionalized water-soluble column[5]arene and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0052] The bis-imino functionalized pillar [5] arene (3) has the following structural formula:

[0053]

[0054] The present invention also provides a method for preparing the above-mentioned bis-imino functionalized pillar[5]arene, the specific implementation route is as follows:

[0055]

[0056] a. The synthesis of bisthiophene functionalized pillar [5] arenes (1), the specific steps are as follows:

[0057]

[0058] Tetrakistriphenylphosphine palladium (133.0 mg, 8%) was added to bistrifluoromethyl functionalized column[5]arene (1.4780 g, 1.5 mmol), 2-thiopheneboronic acid (867.8 mg, 6 mmol) under nitrogen atmosphere and sodium carbonate aqueous solution (1.85mol / L, 10mL) in 40mL redistilled tetrahydrofuran solution. The mixture was reacted at 75° C. for 24 h, and then the solvent was spin-dried in vacuo. Residue with CH 2 Cl 2 / H 2 O system extraction, the organic layer was collected and then dried with anhydrous magnesium sulfate, filtered, the organic laye...

Embodiment 2

[0069] According to the carbon dioxide adsorption simulation experiment reported by Radu Custelcean's research group (Seipp C A, Williams N J, Kidder M K, et al. CO 2 capture from ambient air by crystallizationwith a guanidine sorbent[J].Angewandte Chemie, 2017,129(4):1062-1065.), the bis-iminoguanidine functionalized water-soluble column [5] aromatic hydrocarbon application prepared in Example 1 In acid gas detection, the specific steps are as follows:

[0070]

[0071] (1) Suspend 1 eq of bis-iminoguanidine functionalized water-soluble column [5] aromatics (P [5] BIG) in an equal volume of deionized water and 5-6 eq of NaHCO with a concentration of 1 mol / L 3 In the aqueous solution, stir at room temperature for 4-12h. After the reaction, filter with suction, and the obtained solid is analyzed by thermogravimetric (TGA).

[0072] (2) It can be seen from the thermogravimetric (TGA) analysis diagram that ( figure 2 ), compared with P[5]BIG suspended in deionized water, a...

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Abstract

The invention discloses a class of iminoguanidine functionalized water-soluble pillar[5]arene, its preparation method and application. The general structural formula of this type of compound is as follows: wherein R is C 1 ~C 10 A linear or branched alkoxy group; n is an integer, and the value range of n is 1‑5; the dotted line in the structural formula represents the pillar [5] arene ring structure on the repeating unit of the main molecule. The preparation method comprises the following steps: (1) preparing thiophene-functionalized pillar[5]arenes with trifluoromethyl-functionalized pillar[5]arenes; (2) preparing aldehyde-functionalized pillar[5]arenes; ( 3) Final preparation of iminoguanidine functionalized pillar[5]arene. The pillar[5]arene involved in the present invention contains a pillar framework composed of five benzene rings and five methylene groups, can be connected with up to ten iminoguanidine groups, and contains multiple recognition sites. The preparation method of the invention has the advantages of cheap raw materials, few reaction steps, mild conditions, simple operation and high yield.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a class of iminoguanidine-functionalized water-soluble columnar[5]arene and its preparation method and application. [0002] technical background [0003] Pillararenes, as a new generation of macrocyclic host molecules after crown ethers, cyclodextrins, calixarenes and cucurbiturils, have attracted extensive attention from chemists because of their unique chemical structures and physicochemical properties. The report of pillararene opened a new chapter of supramolecular chemistry, and also brought new opportunities and challenges to the research of supramolecular chemistry. [0004] Since the early studies on pillararenes were limited to organic solvents, which limited their application in the biological field, the synthesis and research of water-soluble pillararenes are particularly important for expanding their applications in the biological field. Carboxylate ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/22C09K11/06G01N5/04
CPCC07D333/22C09K11/06G01N5/04C09K2211/1011C09K2211/1092
Inventor 曹德榕朱恒敏唐浩汪凌云
Owner SOUTH CHINA UNIV OF TECH
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