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Monosubstituted metal phthalocyanine and synthesis and separation method and application thereof

A metal phthalocyanine and separation method technology, applied in the direction of medical preparations containing active ingredients, organic active ingredients, drug combinations, etc., can solve the problems of limited experimental conditions, unsuitable for wide application, etc., achieve low phototoxicity and side effects, Enhanced selective uptake rate, clear composition and structure effects

Inactive Publication Date: 2011-05-25
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] These methods promote the separation of mixtures to a certain extent, but are also limited by experimental conditions and are not suitable for a wide range of applications.

Method used

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  • Monosubstituted metal phthalocyanine and synthesis and separation method and application thereof
  • Monosubstituted metal phthalocyanine and synthesis and separation method and application thereof
  • Monosubstituted metal phthalocyanine and synthesis and separation method and application thereof

Examples

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Embodiment 1

[0033] Mono-substituted metal phthalocyanine, the structural formula of the mono-substituted metal phthalocyanine is:

[0034] Me in the described structural formula represents a divalent metal atom, and taking zinc Zn as an example, R in the structural formula is C 1 -C 10 substituted alkyl with tertiary nitrogen or C 1 -C 10 The substituted aralkyl group with tertiary nitrogen, taking (dimethylaminophenoxy group) as an example, according to the molar ratio, the structural formula is The substituted phthalonitrile 1 and phthalonitrile 3 are reacted in n-pentanol, the molar ratio of the n-pentanol to the substituted phthalonitrile is 10:1, and the reaction is preferably at 130 °C, the reaction time is preferably 22 hours, and a mixture containing mono-(dimethylaminophenoxy) substituted metal phthalocyanine is generated, and the obtained mixture is separated by dry column chromatography.

Embodiment 2

[0036] In the above synthesis and separation method of monosubstituted metal phthalocyanine, the metal salt is acetate or metal halide, taking zinc acetate as an example, the molar ratio of zinc acetate to substituted phthalonitrile is preferably 1:1 ; The organic base is 1,8-diazabicyclo[5,4,0]undecene-7 (DBU) or 1,5-diazabicyclo[4,3,0]nonane- 5-ene (DBN) or pyridine, preferably DBU, the molar ratio of DBU to substituted phthalonitrile is preferably 4:1; the reaction is preferably at 120°C-200°C, especially at 130°C, and the reaction time is preferably 22 Hour.

Embodiment 3

[0038] The above monosubstituted metal phthalocyanine and its synthesis and separation method, the dry column chromatography comprises the following steps: a. dissolving the mixture and loading it on a separation column containing dry silica gel; b. The mixture is separated by washing the separation column with an eluent containing tetrahydrofuran and / or n-hexane and / or petroleum ether.

[0039] The separation of the present invention uses dry column chromatography for chromatographic separation, using a standard glass chromatography column and commercially available silica, and using the above-mentioned eluent to rinse, so that the nitrogen-containing monosubstituted phthalocyanine complex can be obtained Good separation. Dry column chromatography is an improved chromatographic technique. All mixtures that can be separated by thin layer chromatography, including those that cannot be separated on the "wet column", can be separated on the dry column. Using this method, prepara...

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Abstract

The invention discloses monosubstituted metal phthalocyanine and a synthesis and separation method and application thereof. The conventional synthesis and separation of a metal phthalocyanine coordination compound are limited by experimental conditions and are not suitable to be widely applied. The monosubstituted metal phthalocyanine is prepared by the following steps of: reacting substituted phthalonitrile 1 with substituted phthalonitrile 3 in the presence of n-amyl alcohol, DMF (N,N-dimetbylformamide) or DMSO (dimethyl sulphoxide) according to a molar ratio; adding metal salt and organic base, wherein the molar ratio of the metal salt to the substituted phthalonitrile 1 is 1:1-1:5, the molar ratio of the organic base to the substituted phthalonitrile 1 is 3:1-10:1, the molar ratio of the n-amyl alcohol, the DMF or the DMSO to the substituted phthalonitrile is 10:1-20:1 and the reaction is performed at the temperature of between 120 and 200 DEG C for 15 to 30 hours to generate a monosubstituted metal phthalocyanine-containing mixture; and separating the mixture by a dry-column chromatography. The method is used for preparing new monosubstituted metal phthalocyanine.

Description

Technical field: [0001] The invention relates to a monosubstituted metal phthalocyanine, its synthesis, separation method and application. The phthalocyanine derivative is a new type of photosensitizer, which has characteristic absorption and fluorescence in the red light region of the visible spectrum. Background technique: [0002] According to literature reports, the photosensitizing activity of phthalocyanine is affected by the aggregation state and the chemical structure of the photosensitizer. Therefore, preparing monomers with a single structure, studying their structure-activity relationship, and solving their solubility and aggregation properties have become the current Research focus, thereby promoting the in-depth study of the second generation of photosensitizers. [0003] For asymmetric phthalocyanine complexes, the usual statistical condensation method will result in a mixture of some different substituted phthalocyanines. For existing reports, in order to obta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K31/409A61K41/00A61P35/00
Inventor 段武彪褚华翎贺春英孟宪梓吴谊群
Owner HEILONGJIANG UNIV
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