A kind of [2]rotaxane based on pillar aromatics and its preparation and application

A technology for pillar aromatic hydrocarbons and rotaxanes, which is applied to [2]rotaxane and its preparation and application in catalytic coupling reactions, can solve problems such as less research on properties, and achieve the effect of improving catalytic efficiency

Active Publication Date: 2022-07-22
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

More importantly, the current research on [2] rotaxanes based on pillararene mainly focuses on its structure, and there are few studies on its properties.

Method used

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  • A kind of [2]rotaxane based on pillar aromatics and its preparation and application
  • A kind of [2]rotaxane based on pillar aromatics and its preparation and application
  • A kind of [2]rotaxane based on pillar aromatics and its preparation and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of pillararene [2]rotaxane, the synthetic route is as follows figure 1 shown.

[0024] The specific steps are: weigh 0.200g of guest G1 in a 50mL round-bottom flask, 1mmol (0.890g) of ethoxy column [5] arene, 5,5-dimethylcyclohexanedione (2.2eq. about 0.146g) and Malononitrile (2.2eq. about 0.066g) was dissolved in 10mL mixed solvent (EtOH:CHCl 3 =1:1), add 2 drops of piperidine dropwise. The reaction system was heated to reflux for 3h under magnetic stirring, and the reaction progress was detected by TCL. After the reaction was completed, the system was concentrated, and the crude product was separated by thin layer chromatography (DCM:MeOH=25:1). Recrystallization from ethanol, suction filtration to obtain light yellow solid R1.

[0025] Compounds R2, R3, R4, R5 were synthesized by the same method.

[0026] By hydrogen spectrum ( 1 H NMR), carbon spectrum ( 13 C NMR), high-resolution mass spectrometry (HR-ESI-MS), two-dimensional nuclear magneti...

Embodiment 2

[0036] Preparation of Pd Catalysts (Pd@R3) Based on Pillar Arene[2]rotaxane R3

[0037] Because there are two triazole groups on the [2] rotaxane axis prepared by the present invention, which can coordinate with Pd to form the [2] rotaxane hinge together to form a supramolecular polymer material with Pd , the new catalyst.

[0038] preparation process such as Figure 5 shown.

[0039]Specific steps: add 0.18g of column aromatic [2]rotaxane R3 and 5mL of acetonitrile to a 10mL round-bottomed flask, stir until R3 is completely dissolved, and then add AgNO 3 0.02g, continue to stir for 1 hour, filter out the solvent, wash twice with water to obtain catalyst Pd@R3.

[0040] The as-prepared catalyst Pd@R3 was characterized by transmission electron microscopy and energy dispersive analysis, as shown in Image 6 shown.

Embodiment 3

[0042] Catalyst Pd@R3 Catalytic Effect Test

[0043] The catalytic effect was tested by using the prepared new catalyst to catalyze the Suzuki-Miyaura coupling reaction.

[0044] The table below shows the catalysts Pd@R3 and Pd@3 based on rotaxane R3 and the precursor Pd(NO 3 ) 2 comparison of the catalytic effect.

[0045]

[0046] Reaction conditions: phenyl triflate (1.00 mmol), pyridine 4-boronic acid (1.50 mmol), K 2 CO 3 (2.00 mmol), catalyst (0.50 mol% Pd), DMF (5 mL), 100°C. Yields were determined by GC / MS (Agilent 1260).

[0047] From the above results, it can be seen that the catalyst of the present invention not only has good catalytic efficiency, but also can be recycled.

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Abstract

The invention provides a pillar aromatic-based [2]rotaxane and its preparation and application in catalytic coupling reaction, belonging to the technical field of organic synthesis. The present invention utilizes the host-guest complex between the pillararene and the neutral guest to successfully and efficiently construct a new type of pillararene-based [2]rotaxane, and further coordinate the pillararene [2]rotaxane with Pd. A new type of catalyst is prepared, which not only has good catalytic efficiency, but also can be recycled.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a pillar aromatic-based [2]rotaxane and its preparation and application in catalytic coupling reaction. Background technique [0002] Mechanical interlocking structures have been widely used in biotechnology and nanoscience in recent years due to their excellent structural characteristics. [2] Rotaxane, as a typical mechanical interlocking structure, is composed of a dumbbell-shaped shaft and a large ring sleeved on the shaft. So far, many macrocyclic compounds have been used to prepare [2]rotaxanes, such as cyclodextrin, calixarene, cucurbituril, etc. Columnarenes, as the latest class of macrocyclic host compounds, are a class of highly symmetrical oligomeric columnar compounds obtained by bridging hydroquinone ether and its derivatives through methylene at the 2,5-position. Compared with crown ether and calixarene, pillararene has a more rigid structure ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C08G83/00B01J31/22C07D213/16C07D213/127
CPCC07D405/14C08G83/008B01J31/1691B01J31/1815C07D213/16C07D213/127B01J2531/824B01J2531/0213B01J2231/4211
Inventor 姚勇郭浩严鑫胡兰萍陈婷婷王锦丁月袁小磊汪洋卢冰
Owner NANTONG UNIVERSITY
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