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C60 derivative containing cyclic phenyl imine ester structure and method for preparing the same

A technology of cyclophenyl imide esters and derivatives, applied in the field of fullerene derivatives

Inactive Publication Date: 2009-01-21
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This type of reaction and compound structure have not been reported yet

Method used

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  • C60 derivative containing cyclic phenyl imine ester structure and method for preparing the same
  • C60 derivative containing cyclic phenyl imine ester structure and method for preparing the same
  • C60 derivative containing cyclic phenyl imine ester structure and method for preparing the same

Examples

Experimental program
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Effect test

Embodiment 16

[0028] Example 1 [6,6] Cyclophenylimidate C 60 preparation of

[0029] In 100mL of 0.05M tetrabutylammonium perchlorate in benzonitrile solution, add 200mg C 60 , at N 2Under the protection of , the saturated calomel electrode was used as the reference electrode, and the reduction potential of -1.6V was applied to carry out the controlled potential bulk electrolysis. Check the cyclic voltammetry of the solution until an irreversible oxidation peak appears at -0.51V (eg figure 1) , to stop the electrolytic reduction. Adjust the potential to 0V, and carry out oxidation electrolysis to complete. The solvent was removed by rotary evaporation, washed with methanol to remove tetrabutylammonium perchlorate, filtered, and dried in a vacuum oven to give [6,6]cyclophenylimidate C 60 crude product. Taking Buckyprep as the separation, using toluene as mobile phase, separating and purifying by high-performance liquid chromatography, and finally obtaining pure [6,6] cyclophenylimidate...

Embodiment 2

[0030] Example 2 [6,6] Cyclophenylimidate C 60 preparation of

[0031] A benzonitrile solution of 0.5M tetrabutylammonium perchlorate was used for the reaction, the applied potential was -1.0V, and the rest of the operations were as in Example 1.

Embodiment 3

[0032] Example 3 [6,6] Cyclophenylimidate C 60 preparation of

[0033] A 0.2M tetrabutylammonium perchlorate solution in benzonitrile was used for the reaction, the applied potential was -1.2V, and the rest of the operations were as in Example 1.

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Abstract

The invention relates to a derivative of a C60 containing a cyclobenzene imine ester and a method for preparing the same. The method comprises the following steps that a C60<3-> produced through electrochemical deoxidization reacts with a trace amount of water and benzonitril to produce [6,6] cyclobenzene imine ester C60, which is the derivative of C60 containing a cyclobenzene imine ester with the novel structure for the first time. The compound further reacts with benzyl bromide to produce 1,4- dibenzyl-2,3- cyclobenzene imine ester C60. The compound has the structure of a five-element zoline ring, which is determined through single crystal X-ray diffraction, high resolution mass spectrum, and magnetic resonance imaging. The results suggest that the method is capable of efficiently synthesizing the novel derivative of the C60 with the structure of zoline ring. The compound provided by the invention is estimated to have the prospect of application to medical field and the filed of photoelectrical conversion materials, certain potential activity against bacteria, and potential prospect in application to photoelectrical conversion.

Description

technical field [0001] The present invention relates to the C containing ring phenylimide ester structure 60 Derivatives and preparation methods involving the use of C 60 Anion, preparation and characterization of a class of C containing cyclophenylimidate structure 60 Derivatives belong to the technical field of fullerene derivatives. Background technique [0002] Fullerene compounds are all-carbon three-dimensional cage molecules, which are another form of carbon in nature following graphite, diamond and amorphous carbon. They are considered as three-dimensional analogues of organic planar two-dimensional benzene molecules, which have broad application prospects and have aroused worldwide research interests since their discovery. Its own and corresponding chemical derivatives have shown good application properties in photoelectric conversion, organic electronic devices, catalysis, biology and medicine. At present, the development of new preparation methods of fullerene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/52C01B31/02
Inventor 高翔李芳芳
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI