Thermally activated delayed fluorescent polymer and application thereof

A fluorescent polymer, thermal activation delay technology, used in luminescent materials, drug combinations, photodynamic therapy, etc., can solve the problems of fluorescence quenching, loss of photodynamic efficiency, leakage, etc., to achieve easy operation, improve diagnosis and treatment efficiency, The effect of high fluorescence quantum yield

Pending Publication Date: 2022-02-11
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the organic small molecule PS is used to construct anti-tumor diagnostic and therapeutic reagents, it is also easy to leak from the nano-encapsulation system and aggregate to cause fluorescence quenching and loss of photodynamic efficiency.

Method used

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  • Thermally activated delayed fluorescent polymer and application thereof
  • Thermally activated delayed fluorescent polymer and application thereof
  • Thermally activated delayed fluorescent polymer and application thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0071] The preparation method of the integrated nano-reagent for diagnosis and treatment based on a heat-activated delayed fluorescent polymer includes: reprecipitation method, molecular micelle carrier, thin film dispersion method, reflux precipitation method and other common organic semiconductor nano-reagent preparation methods.

[0072] The method of reprecipitation method to prepare a kind of nano-reagent for activating delayed fluorescent polymer is as follows: first, organic semiconductor and functional coating agent (such as PSMA or DSPE-PEG2000, etc.) are dissolved in tetrahydrofuran (THF) respectively, and the concentration is 1 mg / mL solution. After stirring overnight under inert gas protection conditions, the coating agent solution was filtered with a 7 μm glass fiber filter to remove insoluble substances in the bath solution. Then, the above two solutions are mixed in a certain proportion.

[0073]For example, 1 mg / mL organic semiconductor and 0.2 mg / mL PSMA in ...

Embodiment 1

[0081] This embodiment provides a conjugated polymer A based on thermally activated delayed fluorescence. The structural formula of the conjugated polymer A is as follows:

[0082]

[0083] Formula A

[0084] The synthetic route of the conjugated polymer is shown in general formula A.

[0085] Take 0.40g (0.57mmol) 2,2'-(2-(4-(bis(4-bromophenyl)amino)phenyl)anthracene-9,10-dialkylene)dimethylnitrile, 0.28g (1.42mmol) (2,5-dimethyl-1,4-phenylene) diboronic acid and 0.47g (0.85 mmol) 2,7-dibromo-9,9-dioctyl-9H-fluorene were added to 50mL reaction tube, then add 2MCs to the reaction tube in sequence 2 CO 3 (aq) (1mL), 9.2mg (0.008mmol) catalyst tetrakistriphenylphosphine palladium, 5.3mg (0.013mmol) ligand methyl trioctyl ammonium chloride, 5mL anhydrous toluene, at 95 ℃ and argon protection Under the conditions, the reaction was stirred for 96 hours to obtain a polymer. After the polymer is cooled to room temperature, slowly pour it into 150mL of methanol to form a preci...

Embodiment 2

[0087] This embodiment provides a conjugated polymer B based on polycyclic aromatic hydrocarbons. The general structural formula B of the conjugated polymer is as follows:

[0088]

[0089] Formula B

[0090] The synthetic route of the conjugated polymer is shown in general formula B.

[0091] Take 0.50g (0.73mmol) 2,2'-(2-(4-(bis(4-bromophenyl)amino)phenyl)anthracene-9,10-dialkylene)dimethylnitrile, 1.17g (2.44mmol) (9,9-dioctyl-9H-fluorene-2,7-diyl)diboronic acid and 0.96 g (1.71mmol) 2,7-dibromo9-(heptadecan-9-yl) -9H-carbazole was added to a 50mL reaction tube, and 2MCs were added to the reaction tube in turn 2 CO 3 (aq) (1mL), 9.2mg (0.008mmol) catalyst tetrakis triphenylphosphine palladium, 5.3mg (0.013mmol) ligand methyl trioctyl ammonium chloride, 5mL anhydrous toluene, at 95 ℃ and argon protection Under the conditions, the reaction was stirred for 96 hours to obtain a polymer. After the polymer is cooled to room temperature, slowly pour it into 150mL of methan...

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Abstract

The invention discloses a thermally activated delayed fluorescent polymer and application thereof. In the general formula of the thermally activated delayed fluorescent polymer, X represents a connection mode between a benzene ring A and a benzene ring B, and the connection mode comprises that the benzene ring A and the benzene ring B are connected without X, connection is achieved by a single bond, and connection is achieved through any one of -NR1-, -O- and -S-, m+n=0.5, and m is greater than 0 and greater than 0.5. AR1 is substituted benzene, naphthalene, fluorene, carbazole, spirofluorene, anthracene and xanthene, and the substitution on the AR1 is one of a C1-C20 straight chain substituent group, a C1-C20 branched chain substituent group, a C1-C20 straight chain alkoxy group or a C1-C20 branched chain alkoxy group. According to the technical scheme, the advantages of high fluorescence quantum efficiency, relatively long emission wavelength, high photodynamic activity and the like are obtained through a simple synthesis means, and the compound can be used as an active component of a nano reagent for biomedical application.

Description

technical field [0001] The invention relates to a thermally activated delayed fluorescent polymer and its application, which can be used in the technical field of flexible photoelectric organic semiconductors. Background technique [0002] Malignant tumor (cancer) has become one of the most harmful diseases to human health and safety. In clinical treatment, surgery, radiotherapy, and chemotherapy have made considerable progress, but the complex pathogenesis of malignant tumors, easy recurrence and high metastasis make it difficult to say that the above common treatment methods are successful. For example, chemotherapy not only has systemic toxicity and multidrug resistance, but also often damages surrounding healthy tissues, ultimately affecting patient survival. In addition, in addition to malignant tumors, inflammation-related bacterial and fungal infections, Parkinson's disease and other senile degenerative diseases also face the problem of fewer and fewer specific drugs...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06A61K41/00A61K49/00A61P31/04A61P35/00
CPCC08G61/12C08G61/124C09K11/06A61K41/0057A61P35/00A61P31/04A61K49/0019C09K2211/1416C09K2211/1433C09K2211/1466C08G2261/122C08G2261/143C08G2261/149C08G2261/1434C08G2261/312C08G2261/3142C08G2261/3162C08G2261/3241C08G2261/354C08G2261/411C08G2261/522
Inventor 傅妮娜章胜裕赵保敏汪联辉刘梦梦褚兴胜
Owner NANJING UNIV OF POSTS & TELECOMM
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