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1-3 substituted aryloxide dendritic phthalocyanine complexes as well as preparation method and use thereof

A technology of dendritic and substituting aryl ethers, which is applied in the field of 1-3 substituting aryl ether dendritic phthalocyanine complexes and its preparation, achieving the effects of easy interaction, good water solubility and high quantum yield

Inactive Publication Date: 2009-10-28
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no reports of 1-3 generation aryl ether dendritic phthalocyanine complexes whose end groups are carboxyl and cyano groups

Method used

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  • 1-3 substituted aryloxide dendritic phthalocyanine complexes as well as preparation method and use thereof
  • 1-3 substituted aryloxide dendritic phthalocyanine complexes as well as preparation method and use thereof
  • 1-3 substituted aryloxide dendritic phthalocyanine complexes as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] In Example 1, the process 2) carbon tetrabromide was changed to 8g, triphenylphosphine was changed to 4g and tetrahydrofuran was changed to 20mL, and the reaction time was changed to 2h. Other reaction conditions were the same, and 4.0 g of white powdery solid substance (2) was obtained with a yield of 65.0%.

[0081] In process 4), carbon tetrabromide was changed to 15g, triphenylphosphine was changed to 8g and tetrahydrofuran was changed to 35mL, and the reaction time was changed to 2.5h. Other reaction conditions were the same, and 5.04 g of white powdery solid substance (4) was obtained with a yield of 80.0%.

[0082] In process 5), carbon tetrabromide was changed to 30g, triphenylphosphine was changed to 16g and tetrahydrofuran was changed to 60mL, and the reaction time was changed to 3.0h. Other reaction conditions were the same, and 5.25 g of white powdery solid substance (5) was obtained with a yield of 82%.

specific Embodiment 3

[0083] In Example 1, the reaction temperature of process 6) is 80° C., and other reaction conditions are the same, and the yield of the obtained substance (6) is 45.0%.

[0084] Process 7) The reaction temperature is 80°C, other reaction conditions are the same, and the yield of substance (7) is 30.0%.

[0085] Process 8) The reaction temperature is 80°C, other reaction conditions are the same, and the yield of substance (8) is 22.0%.

specific Embodiment 4

[0086] Synthetic method is the same as embodiment one, in process 9)-14), replaces zinc acetate with aluminum trichloride, other process is unchanged, obtains four-[3,5-bis-(4-cyanobenzyloxy)- 1-Methyleneoxyphenyl] aluminum phthalocyanine [G 1 -AlPc(CN) 8 ], productive rate 65%.IR (KBr / cm -1 ): 3449, 2921, 2231, 1601, 1452, 1168, 1059, 826, 640. 1 H NMR (400MHz, DMSO-d 6 , δ / ppm): 7.68(s, 4H), 7.25-7.26(d, J=4Hz, 4H), 7.18~7.19(d, J=4Hz, 4H) 7.66~7.68(d, J=8Hz, 16H) , 7.46~7.48 (d, J=8Hz, 16H), 6.58 (s, 8H), 6.52 (s, 4H), 5.06 (s, 24H). MALDI-TOF-MS: m / z=2068 [M+H 3 o + ]. Four-{3,-di-[3,5-bis-(4-cyanobenzyloxy)-1-methoxyphenyl]-1-methoxyphenyl}aluminum phthalocyanine[G 2 -AlPc(CN) 16 ], yield 62%. IR (KBr / cm -1 ): 3450, 2920, 2230, 1600, 1450, 1251, 1153, 1067, 822, 640. 1 H NMR (400MHz, DMSO-d 6 , δ / ppm): 7.81~7.83(d, J=8Hz, 32H), 7.56~7.58(d, J=8Hz, 32H), 7.39(s, 4H), 7.30(s, 4H), 7.20~7.22( d, J=8Hz, 4H), 6.70(s, 16H), 6.61(s, 12H), 6.57(s, 8H), 5.18(s, 40H),...

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Abstract

The invention discloses a 1-3 substituted aryloxide dendritic phthalocyanine complexes as well as a preparation method and use thereof, which includes the steps of: firstly synthesizing tree-shaped 1-3 alcohol molecules with 1-3 substituted cyano as end-group by Frechet synthesizing method. Then, synthesizing corresponding phthalocyanine precursor containing tree-shaped molecule using '1-3' substituted cyano as end-group from reaction of 4-nitro phthalonitrile with '1-3' substituted alcohol respectively. Subsequently, synthesizing corresponding aryloxide dendritic phthalocyanine using '1-3' substituted cyano-containing end-group from '1-3' substituted tree-shaped molecule phthalocyanine precursor ring using cyano as end-group. As well as hydrolyzing aryloxide dendritic phthalocyanine containing cyano end-group into '1-3' aryloxide phthalocyanine using carboxy group as end-group. The invention also discloses application of 1-3 substituted aryloxide dendritic phthalocyanine complexes in photosensitive agent for photodynamic therapy, and the phthalocyanine has the advantages that the phthalocyanine is not liable to form into aggregates under high concentration, the quantum productivity of singlet oxygen is high, and the light-sensitive activity of the photosensitive agent is high.

Description

Technical field: [0001] The invention belongs to the field of complexes, in particular to a 1-3 generation aryl ether dendritic phthalocyanine complex and a preparation method thereof. The complex is used as a photosensitizer for photodynamic therapy of wet macular degeneration diseases and cancers. 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. They are considered to be a class of Potential photosensitizer. Due to the strong π-π interaction between phthalocyanine molecules, it is easy to aggregate, thereby reducing the fluorescence quantum yield of the ...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K31/409A61K41/00
Inventor 彭亦如张宏
Owner FUJIAN NORMAL UNIV
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