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Advanced rotaxane and synthesis method thereof

A synthetic method and rotaxane technology, applied in the field of synthesis of organic compounds, can solve the problems of slow reaction and low yield, and achieve the effect of fast reaction rate and suitable reaction conditions

Inactive Publication Date: 2018-09-04
王诒凡 +1
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  • Application Information

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Problems solved by technology

[0005] The synthesis of rotaxanes is currently mainly constructed by threading-end capping, slip-in, template synthesis or "threading-condensation ring". Generally, the yield is low or the reaction is very slow. It is also used in the synthesis of higher rotaxanes has limitations

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  • Advanced rotaxane and synthesis method thereof
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Embodiment 1

[0018] The synthetic route is as follows:

[0019]

[0020] Dibenzo-24-crown-8 (250 mg, 0.56 mmol) and N-(anthracen-9-ylmethyl)-3-(4-cyanophenoxy)propan-1-ammonium hexafluorophosphate (285 mg, 0.56 mmol) was dissolved in 10 ml of dichloromethane and stirred at room temperature for 3 hours. Add trifluoromethanesulfonic acid (85 mg, 0.56 mmol) to the above reaction solution, stir overnight at room temperature, quench the reaction solution with ice water, extract with dichloromethane (2×50 ml), wash with water, and separate the organic layer , dried over anhydrous sodium sulfate, and spin off the solvent under reduced pressure to obtain a branched rotaxane (465 mg), with a yield of 87%. 1 H NMR (400MHz, CD 3 D) δ: 1 H NMR (400 MHz, CDCl 3, 295K): δ 8.64 (d, J = 8.8 Hz, 6H), 8.48 (s, 3H), 8.27-8.23 (m, 6H), 7.97 (d, J = 8.4 Hz, 6H), 7.90 (d, J = 8.0 Hz, 6H), 7.65-7.41 (m, 24H), 6.91-6.85 (m,12H), 6.75-6.71 (m, 6H), 6.60 (d, J = 8.8 Hz, 6H), 6.48-6.46 (m, 6H), 5.5...

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Abstract

The invention relates to a synthesis method of organic compounds, in particular to advanced rotaxane and a synthesis method thereof. The synthesis method comprises the following steps: dissolving crown ether and ammonium salt into an organic solvent, and stirring at room temperature for 2 to 4 hours; adding trifluoromethanesulfonic acid, and stirring overnight at room temperature; quenching a reaction solution with ice water, extracting by the organic solvent, washing, separating to obtain an organic layer, drying with anhydrous sodium sulfate, decompressing and spinning the solvent to obtainbranched rotaxane. The synthesis method of the advanced rotaxane, disclosed by the invention, has the advantages that researches of the reactions in the fields of advanced rotaxane synthesis, molecular machines, supramolecular polymers and the like are carried out, so that a brand new thinking and certain promotion effects for the development of supramolecular chemistry are realized.

Description

technical field [0001] The invention relates to a synthesis method of organic compounds, in particular to a higher rotaxane and a synthesis method thereof. Background technique [0002] Rotaxane is a molecular assembly composed of one or more ring molecules and one or more chain molecules as axes, the chain molecules as axes pass through the cavity of ring molecules, and larger molecules are combined at both ends to prevent the axis molecules from slipping out, thus forming an inner-locking supramolecular system ( figure 1 ). The 2016 Nobel Prize in Chemistry was awarded to Jean-Pierre Sauvage from the University of Strasbourg, France, James Fraser Stoddart from Northwestern University, and Bernard L. Feringa of the University of Groningen in the Netherlands for their contributions "in the design and synthesis of molecular machines". [0003] The first report of rotaxane can be traced back to the 1960s, but in the following 20 years, due to the lack of effective synthesis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00
CPCC08G83/007
Inventor 王诒凡刘卫东张昭平刘宏泰赵捷陈蔚王颖田世华王磊曹庆玉邓卉邓鑫
Owner 王诒凡
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