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Fluorinated aryl benzyl ether dendritic phthalocyanine silicon complex and its preparation method and application

A technology of fluorinated aryl benzyl ether and substituted aryl benzyl ether, which is applied in the field of fluorinated aryl benzyl ether dendritic phthalocyanine silicon complex and its preparation, to achieve the effect of inhibiting self-aggregation behavior and improving solubility

Active Publication Date: 2016-05-18
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are no reports of fluorinated arylbenzyl ether dendritic phthalocyanine silicon complexes at home and abroad

Method used

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  • Fluorinated aryl benzyl ether dendritic phthalocyanine silicon complex and its preparation method and application
  • Fluorinated aryl benzyl ether dendritic phthalocyanine silicon complex and its preparation method and application
  • Fluorinated aryl benzyl ether dendritic phthalocyanine silicon complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) Dichlorosilicon phthalocyanine (SiPcCl 2 )Synthesis

[0030] Add 1,3-diiminoisoindoline (3.7g, 25.5mmol), silicon tetrachloride (4.2mL) and quinoline (42mL) into a three-necked flask respectively, stir and reflux at 220°C for 30min, and the mixture When the temperature was lowered to 80°C, it was poured into methanol (80 mL), filtered while it was hot, and the filter residue was washed with 35 mL each of toluene, quinoline, methanol and acetone. After drying, 2.2 g of a purple solid was obtained, with a yield of 60%.

[0031] 2) 2-(4-hydroxybenzene)-2'-(4-(4-cyano-benzyloxy)hexafluoropropane (abbreviation: G 1 -F-CN-OH) synthesis

[0032] Add p-cyanobenzyl bromide (2.4g, 12.0mmol), anhydrous potassium carbonate (2.0g, 14.5mmol), 2,2-bis(4-hydroxyphenyl)hexafluoropropane (4.9g, 14.4mmol), acetone (50mL), stirred vigorously at 55°C and refluxed for 48h, filtered, collected the filtrate, and evaporated the solvent under reduced pressure to obtain a white crude produc...

Embodiment 2

[0049] In Example 1, the process 2) was changed to 4.2g of p-cyanobenzyl bromide, 9.0g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 50mL of acetone, 2h of reaction time, and other Under the same reaction conditions, 7.5 g of a white powdery solid substance was obtained, with a yield of 73%.

[0050] In embodiment one, process 3) SiPcCl 2 Change to 0.4g, G 1 -F-CN-OH was changed to 0.8g; the temperature was changed to 150°C and other reaction conditions were the same, the blue-green solid was 0.33g, and the yield was 70.0%.

[0051] In Example 1, the process 4) p-nitrobenzyl bromide was changed to 3.8g, 2,2-bis(4-hydroxyphenyl)hexafluoropropane was changed to 6.0g, acetone was changed to 60mL, the reaction time was changed to 3h, and other Under the same reaction conditions, 5.5 g of a white powdery solid substance was obtained, with a yield of 47%.

[0052] In embodiment one, process 5) SiPcCl 2 Change to 0.5g, G 1 -F-CN-OH was changed to 1.0g; the temperature was change...

Embodiment 3

[0056] In Example 1, the process 2) was changed to 3.2g of p-cyanobenzyl bromide, 6.3g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 30mL of acetone, 3h of reaction time, and other Under the same reaction conditions, 4.7 g of a white powdery solid substance was obtained, with a yield of 46.0%.

[0057] In embodiment one, process 3) SiPcCl 2 Change to 0.3g, G 1 -F-CN-OH was changed to 0.6g; the temperature was changed to 140°C, and other reaction conditions were the same, the blue-green solid was 0.24g, and the yield was 60.0%.

[0058] In Example 1, the process 4) p-nitrobenzyl bromide was changed to 3.6g, 2,2-bis(4-hydroxyphenyl)hexafluoropropane was changed to 5.8g, acetone was changed to 50mL, the reaction time was changed to 4h, and other Under the same reaction conditions, 5.0 g of a white powdery solid substance was obtained, with a yield of 46.0%.

[0059] In embodiment one, process 5) SiPcCl 2 Change to 0.4g, G 1 -F-CN-OH was changed to 0.7g; the temperature was c...

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Abstract

The invention discloses a fluoro aryl benzyl ether dendritic (phthalocyanino) silicon complex as well as a preparation method and applications thereof. The preparation method comprises the following steps: firstly, synthetizing dichloro (phthalocyanino) silicon; then, in the presence of potassium carbonate, reacting p(nitro or cyano, ester, benzophenone) benzyl bromide with 2,2-bi(4-hydroxyphenyl) hexafluoropropane so as to synthetize 2-(4-hydroxyphenyl)-2'-(4-(4-nitro or cyano or ester or benzophenone-benzyloxy); finally, respectively carrying out reflux reaction on dichloro(phthalocyanino) silicon and 2-(4-hydroxyphenyl)-2'-(4-(4-nitro or cyano or ester or benzophenone-benzyloxy) hexafluoropropane in methylbenzene so as to synthetize di-(2-(4-phenoxy)-2'-(4-(4-nitro or cyano or ester or benzophenone-benzyloxy)hexafluoropropane) for axially replacing a silicon (IV) phthalocyanine complex. In such a way, a fluoro dendritic ligand modified phthalocyanine complex becomes a photosensitizer with good photodynamic therapy potential.

Description

technical field [0001] The invention belongs to the field of complexes, in particular to a fluorinated aryl benzyl ether dendritic phthalocyanine silicon complex and its preparation method and application. The complex is used as a photosensitizer for photodynamic treatment of wet macular degeneration diseases and cancers and cell imaging. Background technique [0002] Photodynamic therapy (PDT) is a new approach to treat cancer, HIV and wet macular degeneration-like diseases. The key to photodynamic therapy is the photosensitizer. 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. Potential photosensitizer. Due to the strong π-π interaction between phthalocyanine molecules, it is easy to aggregate, thereby reducing the fluorescence quantum yield of p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/02A61K41/00A61K49/00A61P35/00A61P27/02
Inventor 彭亦如陈婉玲马冬冬
Owner FUJIAN NORMAL UNIV
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