[2]rotaxane based on pillararene as well as preparation and application thereof

A technology for pillar aromatics and rotaxanes, applied in [2] rotaxanes 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: 2020-09-29
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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  • [2]rotaxane based on pillararene as well as preparation and application thereof
  • [2]rotaxane based on pillararene as well as preparation and application thereof
  • [2]rotaxane based on pillararene as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0024] The specific steps are: in a 50mL round bottom flask, weigh 0.200g of guest G1, 1mmol (0.890g) of ethoxypillar[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 3 h under magnetic stirring, and the progress of the reaction was detected by TCL. After the reaction, the system was concentrated, and the crude product was separated by thin-layer chromatography (DCM:MeOH=25:1). Recrystallize with ethanol, and filter with suction to obtain a light yellow solid R1.

[0025] Compounds R2, R3, R4, and 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 NMR (2DNOESY) and theo...

Embodiment 2

[0036] Preparation of Pd Catalyst (Pd@R3) Based on Pillararene[2]rotaxane R3

[0037] Since there are two triazole groups on the [2] rotaxane axis prepared by the present invention based on pillar arene, it can be coordinated with Pd to hinge the [2] rotaxane to form a supramolecular polymer material with Pd , the new catalyst.

[0038] The preparation process is as Figure 5 shown.

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

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

Embodiment 3

[0042] Catalyst Pd@R3 catalytic effect test

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

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

[0045]

[0046] Reaction conditions: phenyl triflate (1.00mmol), pyridinium 4-boronate (1.50mmol), 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] It can be seen from the above results 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 [2]rotaxane based on pillararene as well as preparation and application thereof in catalytic coupling reaction, and belongs to the technical field of organic synthesis. According to the present invention, by using the host-guest complexation between the pillararene and a neutral guest, the novel [2]rotaxane based on the pillararene is successfully and efficiently constructed, a novel catalyst is further prepared through the coordination of the [2]rotaxane based on the pillararene and Pd, and the catalyst has good catalysis efficiency and can be recycled.

Description

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

Claims

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Application Information

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Patent Type & Authority Applications(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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