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Triphenylamine-quaternary ammonium salt type polymer as well as preparation method and application thereof

A triphenylamine and polymer technology, applied in the field of triphenylamine-quaternary ammonium salt polymer and its preparation, can solve the problems of poor biocompatibility and short emission wavelength, and achieve long emission wavelength, deep penetration depth, and damage small effect

Pending Publication Date: 2021-11-02
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The primary purpose of the present invention is to overcome the problems of poor biocompatibility and short maximum emission wavelength in the above-mentioned existing triphenylamine polymers, and provide a triphenylamine-quaternary ammonium salt type polymer

Method used

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  • Triphenylamine-quaternary ammonium salt type polymer as well as preparation method and application thereof
  • Triphenylamine-quaternary ammonium salt type polymer as well as preparation method and application thereof
  • Triphenylamine-quaternary ammonium salt type polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] A kind of triphenylamine-quaternary ammonium salt type polymer, its structural formula is shown in following formula (I):

[0047]

[0048] The preparation method of described triphenylamine-quaternary ammonium salt type polymer is as follows:

[0049] 4,4'-bis(4-pyridyl)triphenylamine (0.04g, 0.1mmol), 1,6-dibromohexane (0.024g, 0.1mmol), and 20mL tetrahydrofuran were added to a 50ml round bottom flask in sequence. After stirring and reacting at 85°C for 48 hours, the solvent was distilled off under reduced pressure, and the filter residue was washed successively with tetrahydrofuran and diethyl ether to obtain 0.048 g of an orange-yellow solid (65% yield). The degree of polymerization of the polymer obtained in this embodiment is 1-15.

Embodiment 2

[0051] A kind of triphenylamine-quaternary ammonium salt type polymer, its structural formula is shown in following formula (II):

[0052]

[0053] The preparation method of described triphenylamine-quaternary ammonium salt type polymer is as follows:

[0054] Mix N,N-bis(4-formylphenyl)aniline (0.03g, 0.1mmol) with 1,1'-(hexane-1,6-diyl)bis(4-methyl Pyridin-1-ium) bromide (0.043g, 0.1mmol), a few drops of piperidine and 20mL of ethanol were added into a 50mL round bottom flask, heated at 90°C under reflux and stirred for 4 hours. After the reaction was completed, it was cooled, distilled under reduced pressure, and washed successively with tetrahydrofuran and diethyl ether to obtain 0.062 g of a red solid (yield 86%). The degree of polymerization of the polymer obtained in this embodiment is 1-10.

Embodiment 3

[0056] A kind of triphenylamine-quaternary ammonium salt type polymer, its structural formula is shown in following formula (III):

[0057]

[0058] The preparation method of described triphenylamine-quaternary ammonium salt type polymer is as follows:

[0059] Combine 5,5'-((phenylazadiyl)bis(4,1-phenylene))bis(thiophene-2-carbaldehyde) (0.046g, 0.1mmol) with 1,1 prepared in step S2 Add '-(hexane-1,6-diyl)bis(4-methylpyridin-1-ium) bromide (0.043 g, 0.1 mmol), a few drops of piperidine and 20 mL of ethanol to a 50 mL round bottom flask , heated at reflux and stirred at 90°C for 4 hours; cooled after the reaction, distilled under reduced pressure, and washed with tetrahydrofuran and diethyl ether in sequence to obtain 0.075 g of a dark red solid (yield 85%). The degree of polymerization of the polymer obtained in this embodiment is 1-14.

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Abstract

The invention discloses a triphenylamine-quaternary ammonium salt type polymer as well as a preparation method and application thereof. Three triphenylamine-quaternary ammonium salt type polymers with strong D-A or D-pi-A structures are synthesized by taking triphenylamine with a spiral non-planar structure as a donor and pyridine cations with a targeting effect as an acceptor and bridging through carbon-carbon double bonds or thiophene. The triphenylamine-quaternary ammonium salt type polymer prepared by the invention has good biocompatibility, light stability and aggregation-induced emission property, can sensitize oxygen to generate active oxygen, is longer in maximum emission wavelength, and has an important application value in the field of photodynamic therapy.

Description

technical field [0001] The invention relates to the technical field of photodynamic therapy, in particular to a triphenylamine-quaternary ammonium salt polymer and its preparation method and application. Background technique [0002] Photodynamic therapy (PDT) is a minimally invasive cancer treatment. Its main mechanism is that the photosensitizer absorbs light, transitions from the excited singlet state to the triplet state through intersystem jumping, and undergoes electron transfer or energy transfer with the ground state oxygen. Generate cytotoxic reactive oxygen species (ROS), such as singlet oxygen ( 1 o 2 ), superoxide anion radicals, and hydroxyl radicals, thereby inducing cancer cell death. Photodynamic therapy has little impact on the living system, few side effects, and low invasiveness, which can improve the quality of life of patients as a whole. Therefore many photosensitizers have been developed for clinical trials. However, traditional photosensitizers of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C07D409/14C09K11/06C08G73/06A61K41/00A61P35/00G01N21/64
CPCC07D213/38C07D409/14C09K11/06C08G73/0627A61K41/0057A61P35/00G01N21/6428C09K2211/1466C09K2211/1433C09K2211/1425C09K2211/1458C09K2211/1092C09K2211/1029C09K2211/1007C09K2211/1014
Inventor 籍少敏唐丽婷马钰程邢龙江何禧瞳霍延平陈文铖
Owner GUANGDONG UNIV OF TECH
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