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Near-infrared light stimulation response type functional macromolecule, intelligent nanometer material and preparation method of intelligent nanometer material

A near-infrared light, stimuli-responsive technology, applied in steroids, organic chemistry, etc., can solve the problem of less intelligent nanomaterials

Pending Publication Date: 2020-10-30
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at this stage, there are few studies on the preparation of smart nanomaterials with near-infrared light-stimulus-responsive functional macromolecules.

Method used

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  • Near-infrared light stimulation response type functional macromolecule, intelligent nanometer material and preparation method of intelligent nanometer material
  • Near-infrared light stimulation response type functional macromolecule, intelligent nanometer material and preparation method of intelligent nanometer material
  • Near-infrared light stimulation response type functional macromolecule, intelligent nanometer material and preparation method of intelligent nanometer material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of the target molecule Chol-CroA-Chol:

[0068] Add carboxylic acid-piperidine-thiophene and cholesterol to a dry 50mL reaction flask, add dry dichloromethane and stir to dissolve, then add the catalyst DMAP, replace nitrogen three times and keep the nitrogen atmosphere, add EDC after half an hour, under the protection of inert gas The reaction was stirred at room temperature for 24 h. After the reaction is completed, it is washed, dried and filtered, the solvent is removed by rotary evaporation, and purified by column chromatography to obtain cholesterol-piperidine-thiophene. Add croconic acid and cholesterol-piperidine-thiophene to a dry 25mL reaction flask, add a dry mixed solvent of toluene and n-butanol, and heat to reflux for 2h. After the reaction was completed, the solvent was removed by rotary evaporation and purified by column chromatography to obtain the target molecule Chol-CroA-Chol. See the H NMR spectrum figure 1 .

Embodiment 2

[0070] Synthesis of the target molecule Boc-NH-CroA-NH-Boc.

[0071] Add Boc-aminomethyl-piperidine and 2-mercapto-thiophene to a dry 50mL reaction flask, add dry toluene and stir to dissolve, replace the nitrogen three times and keep the nitrogen atmosphere, and heat to reflux for 6h. After the reaction, the solvent was removed by rotary evaporation, and purified by column chromatography to obtain Boc-aminomethyl-piperidine-thiophene. Add Boc-aminomethyl-piperidine-thiophene and croconic acid to a dry 25mL reaction flask, add a dry mixed solvent of toluene and n-butanol, and heat to reflux for 2h. After the reaction was completed, the solvent was removed by rotary evaporation and purified by column chromatography to obtain the target molecule Boc-NH-CroA-NH-Boc. See the H NMR spectrum figure 2 .

Embodiment 3

[0073] Synthesis of target molecule Me-DEG-CroA-DEG-Me

[0074] Add carboxylic acid-piperidine-thiophene and diethylene glycol monomethyl ether to a dry 50mL reaction bottle, add dry dichloromethane and stir to dissolve, then add catalyst DMAP, replace nitrogen three times and keep nitrogen atmosphere, add after half an hour EDC, under the protection of an inert gas, stirred at room temperature for 24 h. After the reaction is completed, wash, dry and filter, remove the solvent by rotary evaporation, and purify by column chromatography to obtain diethylene glycol monomethyl ether-piperidine-thiophene. Add croconic acid and diethylene glycol monomethyl ether-piperidine-thiophene to a dry 25mL reaction flask, add a dry mixed solvent of toluene and n-butanol, and heat to reflux for 2h. After the reaction was completed, the solvent was removed by rotary evaporation and purified by column chromatography to obtain the target molecule Me-DEG-CroA-DEG-Me. See the H NMR spectrum ima...

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Abstract

The invention relates to a near-infrared light stimulation response type functional macromolecule, an intelligent nanometer material and a preparation method of the intelligent nanometer material, belonging to a photo-thermal macromolecule, two synthesis methods and the preparation method of the nanometer material taking the photo-thermal macromolecule as a raw material. A piperidine-thiophene-croconic acid-thiophene-piperidine conjugated element is used as a main component, and a plurality of groups are used for modifying the photo-thermal macromolecule, so the overall properties of the macromolecule are regulated and controlled. A solvent replacement method and a self-nucleation method are adopted, and different solvent systems and temperatures are controlled, so various novel photo-thermal nanometer materials with various morphologies such as a spherical shape, a fibrous shape and a sheet shape are prepared. Structural parameters such as morphology, size and the like of the nanometer material can be effectively regulated and controlled through different photo-thermal macromolecule substituent elements, and the nanometer material has good biocompatibility and excellent photo-thermal performance. In the future, the nanometer material is expected to be applied to photothermal therapy, photodynamic therapy, photoacoustic imaging and the like in the field of biomedicine, and haspotential application value.

Description

technical field [0001] The invention relates to a method for designing and synthesizing a new type of near-infrared light-stimulus-responsive macromolecules, and uses the molecules as raw materials to construct nanomaterials with near-infrared light-stimulation intelligent response behaviors. Background technique [0002] In recent years, due to the development of nanotechnology and the unique physical and chemical properties of nanomaterials and new functions that are easy to expand, functional nanomaterials have been widely studied and applied in clinical medicine, biomedicine and other aspects. The structure design of organic molecules is simple and easy to modify, and functional nanomaterials with controllable morphology can be prepared by self-assembly under certain conditions. Since this type of nanomaterial is under the action of non-covalent bonds, it has the advantage of faster stimulus response speed and can be dissociated under certain conditions. Such nanomateri...

Claims

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Application Information

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IPC IPC(8): C07D409/14C07J43/00
CPCC07D409/14C07J43/003
Inventor 贾林任仰鸽卢悦高娟娟杨新豪谢楠刘淑静
Owner SHANGHAI UNIV
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