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Diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, nanoparticles based on diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, and preparation methods thereof

A technology of diketopyrrolopyrrole and nanoparticle, applied in the field of materials, can solve problems such as less research, and achieve the effect of strong photothermal effect, broad application prospect and strong photothermal effect

Active Publication Date: 2020-03-27
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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  • Diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, nanoparticles based on diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, and preparation methods thereof
  • Diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, nanoparticles based on diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, and preparation methods thereof
  • Diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, nanoparticles based on diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, and preparation methods thereof

Examples

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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 argon atmosphere, raise the temperature to 90°C and stir for 0.5h to dissolve it completely, and 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, the preparation of oligomeric nanoparticle

[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 Th...

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Abstract

The invention provides a diphenyl-pyrrolo-pyrrolidinedione conjugated oligomer, nanoparticles based on the conjugated oligomer, and preparation methods thereof. The general structural formula of the conjugated oligomer is shown as a formula I in the specification. The diphenyl-pyrrolo-pyrrolidinedione with good light stability and strong electron withdrawing ability is used as a construction unit,a simple coupling reaction is used as a connection method, and the method for preparing the conjugated oligomer with controllable polymer, long light absorption wavelength and high photo-thermal conversion efficiency is provided. Meanwhile, the invention provides a preparation method of the nanoparticles based on the conjugated oligomer, and a new material and method are provided for the application of the conjugated oligomer as a photo-thermal reagent in biological treatment.

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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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