Crown ether-based rotaxane molecular machine and preparation method thereof

A molecular machine, rotaxane technology, applied in chemical instruments and methods, instruments, organic chemistry, etc., can solve the problems of limited effect, inaccurate, unintuitive detection methods, etc., to achieve sensitive detection methods and reduce steric hindrance. Effect

Active Publication Date: 2021-09-28
ZHEJIANG UNIV OF TECH
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  • Abstract
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  • Claims
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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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  • Crown ether-based rotaxane molecular machine and preparation method thereof
  • Crown ether-based rotaxane molecular machine and preparation method thereof
  • Crown ether-based rotaxane molecular machine and preparation method thereof

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Embodiment Construction

[0049] The present invention will be further described below in conjunction with the accompanying drawings and specific embodiments.

[0050] a kind of like figure 1 The molecular machine shown is prepared from intermediate 1, intermediate 2, and intermediate 3, and the synthesis method is as follows:

[0051] Synthesis of 4-Morpholine-1,8-Dinaphthoic Anhydride

[0052] In a 100mL round bottom flask, under nitrogen protection, 4-bromo-1,8-dinaphthoic anhydride (0.5g, 1.80mmol) was dissolved in 10mL of ethylene glycol methyl ether solution, and 50mg of cuprous iodide and morphine were added The morphine (0.47g, 5.41mmol) was refluxed for 7h, filtered and washed several times with ethanol to obtain compound 4 as a yellow solid (0.29g, 58%). TLC (developing agent: 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=8.3Hz, 1H), 4.02(d, J=4.7Hz, 4H), 3.35...

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Abstract

The invention relates to the field of molecular machines, aims to overcome the defects that an existing molecular machine is unreasonable in structural design, the action effect among different structures in molecules is limited, the detection method is not visual and not accurate enough, and discloses a crown ether-based rotaxane molecular machine and a preparation method thereof. The acid-base property is detected according to the change of the fluorescence intensity of naphthalimide caused by the position difference of a crown ether structure on a chain molecule under acidic and alkaline conditions and the movement of the crown ether structure generated by the change of the acid-base property in a system. Besides, the terpyridyl structure of the molecular machine disclosed by the invention can also generate a coordination effect with metal ions, the inner filtering effect caused by the coordination effect can further quench the fluorescence of naphthalimide, and the metal ions can also be identified and detected according to different quenching capacities of different metal ions to the fluorescence.

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 the protein molecules in the ATPase in the organism 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 interlocked molecules (MIMs) based on rotaxanes or catenanes have been one of the research hotspots in the past 20 years, and their potential application value has attracted widespread attention of scientists. Rotaxane is a typical mechanical interlocking structure composed of dumbbell-shaped shafts and ring-shaped molecules. Through external stimulation (regulation), the position of the cyclic component shuttling on the shaft can be changed, and due to the e...

Claims

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Application Information

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Patent Type & Authority Applications(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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