Triphenylamino dendrimer ligand substituted silicon phthalocyanine and its preparation method and application

A technology of triphenylamine-based and silicon phthalocyanine, which is applied in the field of triphenylamine-based dendritic ligands substituted for silicon phthalocyanine and its preparation, to achieve the effects of inhibiting aggregation behavior and improving performance

Active Publication Date: 2020-08-25
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Finally, there is no report on the substitution of silicon phthalocyanine by triphenylamine-based dendrimer ligands at home and abroad.

Method used

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  • Triphenylamino dendrimer ligand substituted silicon phthalocyanine and its preparation method and application
  • Triphenylamino dendrimer ligand substituted silicon phthalocyanine and its preparation method and application
  • Triphenylamino dendrimer ligand substituted silicon phthalocyanine and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1) Dichlorosilicon phthalocyanine (SiPcCl 2 )Synthesis

[0023] Add 1,3-diiminoisoindoline (7.28 g, 50.15 mmol), silicon tetrachloride (8.3 mL) and quinoline (83 mL) respectively into a three-necked flask, stir and reflux for 30 min at 220 °C , cooled to room temperature, poured into 500mL methanol solution, stirred and stood for about 1h, filtered, and the filter residue was washed with 35 mL each of acetone, methanol, dichloromethane, methanol and other solvents, and after drying, 3.6759 g of purple solid was obtained. The yield was 48.62%.

[0024] ) Synthesis of 4'-(diphenylamino)-[1,1'-biphenyl]-4-ol (abbreviated as TPA-OH in the present invention)

[0025] 4-Bromotriphenylamine (1.260 g, 3.89 mmol), 4-hydroxyphenylboronic acid (0.532 g, 3.86 mmol), tetrakis(triphenylphosphine) palladium Pd(PPh 3 ) 4 (0.140 g, 0.120 mmol), after anhydrous and anaerobic operation, inject THF (50 mL) and 2M K 2 CO 3 (25 mL) and the reaction mixture was stirred and refluxed at ...

Embodiment 2

[0031] The specific steps are the same as in Example 1: in process 2), 4-bromotriphenylamine was changed to (2.52 g, 7.98 mmol), 4-hydroxyphenylboronic acid was changed to (1.06 g, 7.72 mmol), and the reaction temperature was changed to 90°C; The time was changed to 36 h. Other reaction conditions were the same, and 0.62 g of tan powder was obtained with a yield of 23.8%.

[0032] The specific steps are the same as in Example 1: in process 3), dichlorosilicon (IV) phthalocyanine is changed to (0.40 g, 0.654 mmol), TPA-OH is changed to (0.66 g, 1.96 mmol)), and the reaction temperature is changed to 150 o C, the reaction time was changed to 96 h. 8 mg of blue powder was obtained with a yield of 1%.

Embodiment 3

[0034] Concrete steps are the same as embodiment one: K in process 3) 2 CO 3 (0.09 g, 0.654 mmol) was changed to NaH (0.01 g, 0.654 mmol), and other reaction conditions were the same. 5.6 mg of blue powder was obtained with a yield of 1.4%.

[0035] Process 3) K 2 CO 3 (0.09 g, 0.654 mmol) was changed to pyridine (0.05 g, 0.654 mmol), and other reaction conditions were the same. 5.8 mg of blue powder was obtained with a yield of 1.46%.

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Abstract

The invention discloses a triphenylamine-based branch ligand substituted silicon phthalocyanine, a preparation method and an application thereof. 4-bromotriphenylamine and 4-hydroxy phenylboronic acidare catalytically coupled through tetrakis (triphenylphosphine) palladium, so as to acquire a branch precursor 4'-(diphenyl amino)-[1,1'-biphenyl]-4-alcohol; the 4'-(diphenyl amino)-[1,1'-biphenyl]-4-alcohol (TPA-OH) reacts with SiPcCl2 in the presence of methylbenzene and K2CO3, so as to acquire bi-(4-(diphenyl amino)-1-biphenylyloxy) axially substituted silicon phthalocyanine; steric hindranceof a triphenylamine substituted branch structure is capable of restraining the gathering of phthalocyanine to some extent; the triphenylamine with an aggregation-induced emission characteristic is introduced into the branch structure, so that the 'aggregation-induced quenching' effect of phthalocyanine is improved, the optical physical property of phthalocyanine is regulated and the simultaneous execution of fluorescence imaging and photodynamic therapy is realized; the triphenylamine-based branch ligand substituted silicon phthalocyanine can be used as a fluorescence imaging agent and a photodynamic therapy photosensitizer.

Description

technical field [0001] The invention belongs to the field of complexes, in particular to a triphenylamine-based dendritic ligand substituted silicon phthalocyanine and a preparation method thereof and the use of the complex as a photosensitizer for photodynamic therapy and fluorescence imaging for treating tumors and macular degeneration diseases agent application. Background technique [0002] Photodynamic therapy (PDT) is a novel approach for the treatment of a range of cancers, immune diseases and wet macular degeneration. It uses light to excite and enrich photosensitizer molecules (Photosensitizer, PS) inside cancer cells to generate active oxygen and kill cancer cells from cells. Phthalocyanine complexes have a similar skeleton structure to hematoporphyrin, are more stable and easy to modify, and have a maximum absorption wavelength of around 670nm. They are easy to pass through the red light region of human tissues and can be made into pure products. They are conside...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/02C09K11/06A61K41/00G01N21/64
CPCA61K41/0071C07F7/025C09K11/06C09K2211/1007C09K2211/1029C09K2211/1074G01N21/6486
Inventor 彭亦如郭秋梅林昌铨陈秀琴
Owner FUJIAN NORMAL UNIV
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