A kind of rotaxane molecular machine based on crown ether and preparation method

A technology of molecular machines and rotaxanes, applied in chemical instruments and methods, instruments, organic chemistry, etc., can solve the problems of inaccuracy, limited effect, unintuitive detection methods, etc., and achieve the goal of reducing steric hindrance and sensitive detection methods Effect

Active Publication Date: 2022-07-01
ZHEJIANG UNIV OF TECH
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Problems solved by technology

[0006] The purpose of the present invention is to overcome the unreasonable structure design of existing molecular machines, the limited interaction effect between different structures in the molecule; the unintuitive and inaccurate detection method, and provide a more significant interaction effect between different structures in the molecule; relying on fluorescence A crown ether-based rotaxane molecular machine that can detect different metal ions by changing the pH;

Method used

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  • A kind of rotaxane molecular machine based on crown ether and preparation method
  • A kind of rotaxane molecular machine based on crown ether and preparation method
  • A kind of rotaxane molecular machine based on crown ether and preparation method

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Embodiment Construction

[0048] The present invention will be further described below with reference to the accompanying drawings and specific embodiments.

[0049] such as figure 1 The molecular machine shown is prepared from intermediate 1, intermediate 2, and intermediate 3, and the synthesis method is as follows:

[0050] Synthesis of 4-morpholine-1,8-dinaphthoic anhydride

[0051] In a 100 mL round-bottomed flask, under nitrogen protection, 4-bromo-1,8-dinaphthoic anhydride (0.5 g, 1.80 mmol) was dissolved in 10 mL of ethylene glycol methyl ether solution, and 50 mg of cuprous iodide and morphine were added. Phosphate (0.47 g, 5.41 mmol), refluxed for 7 h, filtered and washed with ethanol several times to obtain compound 4 (0.29 g, 58%) as a yellow solid. TLC (developing solvent: petroleum ether: ethyl acetate / 1:1 / v:v) R f =0.39,1H NMR (400MHz, CDCl 3 )δ8.60(d, J=8.4Hz, 1H), 8.54(d, J=8.1Hz, 1H), 8.47(d, J=8.5Hz, 1H), 7.79-7.72(m, 1H), 7.27- 7.25 (d, J=8.3 Hz, 1H), 4.02 (d, J=4.7 Hz, 4H), 3....

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Abstract

The invention relates to the field of molecular machines. In order to overcome the unreasonable structural design of the existing molecular machines, the limited effect between different intramolecular structures, and the unintuitive and inaccurate detection methods, a crown ether-based rotaxane molecular machine is disclosed. Preparation. According to the difference in the position of the crown ether structure on the chain molecule under acidic and basic conditions, and the movement of the crown ether structure according to the change of acidity and alkalinity in the system, which leads to the change of the fluorescence intensity of naphthalimide, the acidity and alkalinity are analyzed. test. In addition, the terpyridine structure of the molecular machine of the present invention can also have a coordination effect with metal ions, and the inner filter effect caused by the coordination effect can further quench the fluorescence of naphthalimide. Different quenching abilities can also identify and detect metal ions.

Description

technical field [0001] The invention belongs to the technical field of molecular machines, and in particular relates to a crown ether-based rotaxane molecular machine and a preparation method. Background technique [0002] Inspired by the phenomenon that protein molecules in ATPase in vivo synthesize ATP through rotation, and the mutual movement between actin and myosin in muscle fibers realizes muscle contraction, chemists have synthesized various artificial molecular machines. Among them, mechanically interlocking molecules (MIMs) based on rotaxane or catenane are one of the research hotspots in the past 20 years, and their potential application value has attracted extensive attention of scientists. Rotaxane is a typical mechanically interlocked structure composed of dumbbell-shaped shafts and ring molecules. Through external stimuli (regulation), the shuttle position of the cyclic component on the shaft can be changed, and due to the existence of the end-capping group, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C07D401/14C09K11/06C09K11/02G01N21/64
CPCC07D401/14C07D405/14C09K11/06C09K11/025G01N21/643G01N2021/6432C09K2211/1033C09K2211/1029C09K2211/1059C09K2211/1007C09K2211/1088Y02P20/55
Inventor 杜光焰陈贤慧陶晓博原静静施俊滔
Owner ZHEJIANG UNIV OF TECH
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