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Diketopyrrolopyrrole conjugated oligomers, nanoparticles based thereon, and their preparation methods

A technology of diketopyrrolopyrrole and diketopyrrolopyrrole, applied in the field of nanoparticles and their preparation, diketopyrrolopyrrole conjugated oligomers, which can solve the problems of less research and achieve strong photothermal effect , Strong photothermal effect, avoid batch effect

Active Publication Date: 2021-05-18
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, judging from the current research results, the development of photothermal reagents is mostly concentrated in the field of organic polymers, while less research has been done on organic oligomer molecules.

Method used

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  • Diketopyrrolopyrrole conjugated oligomers, nanoparticles based thereon, and their preparation methods
  • Diketopyrrolopyrrole conjugated oligomers, nanoparticles based thereon, and their preparation methods
  • Diketopyrrolopyrrole conjugated oligomers, nanoparticles based thereon, and their preparation methods

Examples

Experimental program
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Effect test

Embodiment 1

[0072] Embodiment 1, oligomer ODPP

[0073] according to figure 1 The synthetic route shown for the preparation of thienylpyrrolopyrrole diketopyrrole oligomers (ODPP)

[0074] 1) Synthesis of 3,6-bis(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

[0075] Add sodium tert-amyloxide (24.8g, 225mmol) into 90mL of tert-amyl alcohol under an argon atmosphere, raise the temperature to 90°C and stir for 0.5h to dissolve it completely, drop 2-cyanothiophene (16.4g, 150mmol) After adding to the solution, diisopropyl succinate (12.1 g, 60 mmol) was slowly added dropwise, and the color of the suspension turned dark red. After the addition, the stirring reaction was continued at this temperature for 2h. Lower the reaction temperature to 50°C, then add 65 mL of methanol to dilute, and neutralize with 25 mL of glacial acetic acid, stir at this temperature for 15 min, and cool to room temperature. The reaction mixture was filtered, and the filter cake was extracted with anhydrous ...

Embodiment 2

[0099] Embodiment 2, preparation of oligomer nanoparticles

[0100] This example only provides a method for preparing nanoparticles by using the nanoprecipitation method, and the amphiphile molecules are not limited to those used in this example.

[0101] 1) Weigh the ODPP (0.5mg) prepared in Example 1, dissolve DSPE-PEG-MAL (6mg) in 1mL THF, and sonicate the mixture for 30min;

[0102] 2) Add triethylamine (7.28mg / mL, 34uL) and polyethyleneimine (PEI) (15.875mg / mL, 16uL) to the mixture according to 50% of the oligomer mass, and stir overnight;

[0103] 3) Add the above mixture into 9mL ultrapure water, after ultrasonication for 10min, stir for 5h, and blow inert gas into the solution until all THF volatilizes;

[0104] 4) Dialyze the aqueous solution of nanoparticles (molecular weight cut off is 3500) to remove excess PEI molecules, filter the retentate with a 220nm filter membrane, and store the obtained aqueous solution of nanoparticles at -4°C.

[0105] image 3 The hea...

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Abstract

The present invention provides a diketopyrrolopyrrole conjugated oligomer, nanoparticles based on it and their preparation method, the general structural formula of which is shown in Formula I. The present invention uses diketopyrrolopyrrole, which has good photostability and strong electron-absorbing ability, as a building unit, and uses a simple coupling reaction as a connection method to provide a polymer with controllable preparation, long light absorption wavelength and light Method for Conjugated Oligomers with High Thermal Conversion Efficiency. At the same time, it provides a preparation method based on its nanoparticles, which provides new materials and methods for the application of conjugated oligomers as photothermal reagents in biotherapy.

Description

technical field [0001] The invention belongs to the field of materials, and relates to a diketopyrrolopyrrole conjugated oligomer, nanoparticles based on it, and a preparation method thereof. Background technique [0002] The photothermal effect refers to the phenomenon that after the material is irradiated by light, the photon energy interacts with the lattice, the vibration is intensified, and the temperature rises. Substances with photothermal effect are collectively referred to as photothermal reagents. As photothermal reagents, organic conjugated molecules have excellent photothermal conversion efficiency and overcome the shortcomings of traditional inorganic photothermal reagents in terms of stability and poor biocompatibility. and combination therapy have received extensive attention. [0003] Organic conjugated molecules are organic molecules connected by conjugated bonds, with delocalized π electron clouds, which can efficiently relax in the form of heat after bei...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00A61K41/00A61P35/00
CPCA61K41/0052A61K41/0057A61P35/00C07D519/00
Inventor 邢成芬吴曼曼高冬高梦诗
Owner HEBEI UNIV OF TECH
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