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Carbene-diazo compound-olefine aldehyde terpolymer and application of carbene-diazo compound-olefine aldehyde terpolymer as bidirectional conversion fluorescent material and anti-cancer drug

A technology of terpolymers and diazo compounds, which is applied in the fields of polymer materials and biomedicine to achieve the effects of improving sensitivity, enhancing fluorescence intensity, and low cost

Inactive Publication Date: 2015-01-28
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional up-conversion luminescent materials are all doped with rare earth metals, and mainly fluorides and oxyfluorides, so their biological safety is still a hot and difficult research point.
At the same time, general down-conversion luminescent materials do not have the performance of up-conversion

Method used

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  • Carbene-diazo compound-olefine aldehyde terpolymer and application of carbene-diazo compound-olefine aldehyde terpolymer as bidirectional conversion fluorescent material and anti-cancer drug
  • Carbene-diazo compound-olefine aldehyde terpolymer and application of carbene-diazo compound-olefine aldehyde terpolymer as bidirectional conversion fluorescent material and anti-cancer drug
  • Carbene-diazo compound-olefine aldehyde terpolymer and application of carbene-diazo compound-olefine aldehyde terpolymer as bidirectional conversion fluorescent material and anti-cancer drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Cinnamaldehyde (1.32 g, 0.01 mol) and methyl diazoacetate (MDA) (1.00 g, 0.001 mol) were added to a 10 ml round bottom flask connected to a safety bottle containing mineral oil. React at room temperature for 120 h, cool to room temperature after completion, reprecipitate with chloroform / ether, and dry in vacuo to obtain a polymer.

[0040] figure 1 It is the time-of-flight mass spectrum of the polymer obtained in Example 1. From the spectrogram, it can be resolved that the polymer structure is a terpolymer of carbene, diazo compound and cinnamaldehyde. figure 2 It is its fluorescence spectrum. Fluorescence can be obtained from ultraviolet and near-infrared light excitation, and the fluorescence intensity obtained by near-ultraviolet excitation is not much different from that of ultraviolet excitation, which has a good up-conversion fluorescence effect.

Embodiment 2

[0042] Cinnamaldehyde (1.32 g, 0.01 mol) and ethyl diazoacetate (2.28 g, 0.02 mol) were added to a 10 ml round bottom flask connected to a safety bottle containing mineral oil. Heat to 150° C. for 60 minutes, cool to room temperature after the reaction, reprecipitate with chloroform / n-hexane, and vacuum dry to obtain a polymer.

Embodiment 3

[0044] Add trans-crotonaldehyde (0.70g, 0.01mol) and ethyl diazoacetate (0.57g, 0.005mol) into a 10ml round bottom flask, use toluene as solvent reflux, and the condenser tube is connected to a safety bottle equipped with mineral oil, After reacting for 2 minutes, cool to room temperature, reprecipitate with chloroform / n-hexane, and dry in vacuum to obtain a polymer. image 3 It is its fluorescence spectrum, which can obtain fluorescence from ultraviolet and near-infrared light excitation, and has a good up-conversion fluorescence effect.

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Abstract

The invention discloses a carbene-diazo compound-olefine aldehyde terpolymer and a preparation method thereof. The preparation method comprises the following steps: a diazo compound and olefine aldehyde are used as polymerization reaction monomers and after reaction, reprecipitation, centrifugation and vacuum drying of precipitates are carried out to obtain the product. The polymer is mainly prepared by copolymerization of C1 / C1N2 / C2 and a main chain of the polymer mainly comprises carbene, diazo compound and olefine aldehyde. The polymer not only has a down-conversion fluorescent property, but also has an up-conversion fluorescent property, meanwhile, has high optical stability, can be widely applied to the field of optics and optical detection; meanwhile, the polymer has anti-cancer activity and can be applied to the field of medicine.

Description

technical field [0001] The invention relates to a carbene-diazo compound-enal terpolymer and its use as a bidirectional conversion fluorescent material and anticancer drug, belonging to the fields of polymer materials and biomedicine. Background technique [0002] The concept of carbene was proposed by Eduard Buchner in 1903 when he studied the cyclopropanation reaction of ethyl diazoacetate (EDA). In organic synthesis, carbene has been widely used as an important intermediate. Diazo compounds have the characteristics of simple preparation, relative stability and safety, and are often used as precursors of carbene. Generally, the reaction between diazo compounds and alkenes can be divided into two types: one is denitrogenation to form carbene and cyclopropanation reaction with alkenes; the other is 1,3-dipolar cycloaddition reaction to generate pyrazoline. [0003] The copolymerization reaction of diazo compound and olefin is a rare case of C1 / C1N2 / C2 copolymerization reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/00C09K11/06A61K31/785A61P35/00
Inventor 刘立建李焰陈诚陈芳娟贾响响
Owner WUHAN UNIV
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