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Fluoro aryl benzyl ether dendritic (phthalocyanino) silicon complex as well as preparation method and applications thereof

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: 2014-08-27
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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  • Fluoro aryl benzyl ether dendritic (phthalocyanino) silicon complex as well as preparation method and applications thereof
  • Fluoro aryl benzyl ether dendritic (phthalocyanino) silicon complex as well as preparation method and applications thereof
  • Fluoro aryl benzyl ether dendritic (phthalocyanino) silicon complex as well as preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0030] Add 1,3-diiminoisoindoline (3.7 g, 25.5 mmol), silicon tetrachloride (4.2 mL) and quinoline (42 mL) into a three-necked flask respectively, stir and reflux at 220 °C for 30 min, When the mixture was cooled to 80 °C, it was poured into methanol (80 mL), filtered while 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. The yield was 60%.

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

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

Embodiment 2

[0049] In Example 1, the process 2) was changed to 4.2 g of p-cyanobenzyl bromide, 9.0 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 50 mL of acetone, and 2 h of reaction time , other reaction conditions were the same, 7.5 g of white powdery solid substance was obtained, and the yield was 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 0.33 g, and the yield was 70.0%.

[0051] In Example 1, the process 4) was changed to 3.8 g of p-nitrobenzyl bromide, 6.0 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 60 mL of acetone, and 3 h of reaction time , other reaction conditions were the same, and 5.5 g of 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 changed to 150°C, and other react...

Embodiment 3

[0056] In Example 1, the process 2) p-cyanobenzyl bromide was changed to 3.2 g, 2,2-bis(4-hydroxyphenyl)hexafluoropropane was changed to 6.3 g, acetone was changed to 30 mL, and the reaction time was changed to 3 h , other reaction conditions were the same, 4.7 g of white powdery solid substance was obtained, and the yield was 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 0.24 g, and the yield was 60.0%.

[0058] In Example 1, the process 4) was changed to 3.6 g of p-nitrobenzyl bromide, 5.8 g of 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 50 mL of acetone, and 4 h of reaction time , other reaction conditions were the same, and 5.0 g of 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 tempera...

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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 Applications(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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