Fluorescent fullerene aziridine derivative and preparation thereof

A technology of fullerene aziridine and derivatives, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problem that no one has done fluorescence modification work, and achieve enhanced fluorescence performance and improved fluorescence performance. Effect

Inactive Publication Date: 2009-05-20
SHANGHAI UNIV
View PDF1 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Due to the special structure of fullerenes, the generation of its fluorescence properties is limited. In addition, according to literature review, it is known that almost no one has done the fluorescent modification of fullerene derivatives.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Fluorescent fullerene aziridine derivative and preparation thereof
  • Fluorescent fullerene aziridine derivative and preparation thereof
  • Fluorescent fullerene aziridine derivative and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Preparation of N-n-butyl-4-aziridine [C60]-1,8-naphthalimide

[0022] Method 1: Take 0.1mmol of C 60 , dissolved in 50ml of o-dichlorobenzene, under nitrogen protection at room temperature, slowly heated to 130 ° C, and slowly added dropwise N-n-butyl-4-azido-1,8-naphthalimide solution (0.6 N-n-butyl-4-azido-1,8-naphthalimide of mmol is dissolved in 5ml of o-dichlorobenzene), after the dropwise addition is completed, the temperature is slowly raised to 160° C., heated for 10 hours, filtered off The dissolved substance was concentrated, and the product was purified by toluene column chromatography and dried in vacuo to constant weight to obtain N-n-butyl-4-aziridine[C60]-1,8-naphthalimide, yield 28 %.

[0023] Method 2: put C 60 Mix with N-n-butyl-4-azido-1,8-naphthoimide at a ratio of 1:4, dissolve in 10ml of o-dichlorobenzene, and react with microwave at 800W for 3min under nitrogen protection. After the reaction, the insoluble matter was filtered off, t...

Embodiment 2

[0030] Example 2: Preparation of N-n-dodecyl-4-aziridine [C60]-1,8-naphthalimide

[0031] Method 1: Take 0.1mmol of C 60 , dissolved in 50ml of o-dichlorobenzene, under nitrogen protection at room temperature, slowly heated to 130 ° C, and slowly added dropwise N-n-dodecyl-4-azido-1,8-naphthalimide solution within 1 hour ( 0.6mmol of N-n-dodecyl-4-azide-1,8-naphthalimide was dissolved in 5ml of o-dichlorobenzene), after the dropwise addition was completed, the temperature was slowly raised to 160°C, and the reaction was heated for 6 hours, filtered Insoluble matter was removed, the liquid was concentrated, the product was purified and separated by toluene column chromatography, and vacuum-dried to constant weight to obtain N-n-dodecyl-4-aziridine [C60]-1,8-naphthalimide, Yield 52%.

[0032] Method 2: put C 60 Mix it with N-n-dodecyl-4-azido-1,8-naphthalimide at a ratio of 1:3, dissolve it in 10ml of o-dichlorobenzene, and microwave it at 800W for 4min under nitrogen protect...

Embodiment 3

[0040] Example 3: Preparation of N-hexadecyl-4-aziridine [C60]-1,8-naphthalimide

[0041] Method 1: Take 0.1nmol of C 60 , dissolved in 50ml o-dichlorobenzene, under nitrogen protection at room temperature, slowly heated to 130°C, and slowly added N-hexadecyl-4-azido-1,8-naphthalimide solution dropwise within 1 hour (0.6nmol of N-hexadecyl-4-azido-1,8-naphthalimide was dissolved in 5ml of o-dichlorobenzene), after the dropwise addition was completed, the temperature was slowly raised to 160°C, and the reaction was heated for 6 hours , filter off the insoluble matter, concentrate the liquid, purify and isolate the product with toluene column chromatography, and vacuum dry to constant weight to obtain N-hexadecyl-4-aziridine[C60]-1,8-naphthoyl Imine, 52% yield.

[0042] Method 2: put C 60 Mix it with N-hexadecyl-4-azido-1,8-naphthalimide at a ratio of 1:5, dissolve it in 10ml of o-dichlorobenzene, and microwave it at 800W under nitrogen protection. After 4min, after the reac...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a fluorescent aziridine fullerene derivative and a preparation method thereof. The structural formula of the derivative is Formula 1, wherein, R1 is an alkyl of C1 to C32. Indicated by an ultraviolet and fluorescence performance test, the compound realizes the fluorescence transformation of fullerene by the introduction of a fluorescence block and has an abrupt change in fluorescence performance in comparison with the fluorescence performance of the fullerene so as to greatly improve the fluorescence performance of the fullerene, thereby initially completing the fluorescence transformation of the fullerene. The significance of the transformation is that the invention of the product can provide a new thinking path for research on the application of the fullerene, and can also enhance the value of the fullerene applied to the fields of biomedicine, materials science and the like.

Description

technical field [0001] The invention relates to a fluorescent fullerene aziridine derivative and a preparation method thereof. Background technique [0002] In the field of biomedicine, because most biomolecules have no fluorescence or weak fluorescence, and the detection sensitivity is poor, people use strong fluorescent labeling reagents or fluorescence generating reagents to label or derivatize the analytes to generate covalent fluorescent molecules with high fluorescence intensity. Or non-covalently bound substances, the detection limit is greatly reduced, which is the rapid development of fluorescent probe technology in recent years. Its basic characteristics are high sensitivity and extremely wide dynamic response time. With the continuous development of biotechnology, the requirements for protein, nucleic acid and cell labeling are getting higher and higher. The traditional radiolabeling method is far from being able to meet the current development needs in terms of ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & AuthorityApplications(China)
IPC IPC(8): C07D221/12C09K11/06C01B31/00
Inventor杜蔚琼章建民吴然刘凤瑞梁琴孙骅
OwnerSHANGHAI UNIV