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Ortho-positioned bridged azacrown ether modified phthalocyanin and preparation method and application thereof

A technology of heterocrown ether and azine, applied in the field of preparation of optical functional substances, can solve the problems of high absorption and emission intensity, lack of phthalocyanine compounds, limited clinical application, etc., and achieves high molar absorption coefficient, good amphiphilicity, and improved The effect of transmittance

Active Publication Date: 2013-09-18
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Hematoporphyrin derivatives have shown certain curative effects, but also exposed serious disadvantages: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin has high phototoxicity. It is a mixture and its composition is unstable, so its clinical application is limited, so the development of a new generation of photodynamic drugs (photosensitizers) is an international research hotspot
[0005] On the other hand, since the maximum absorption and emission wavelengths are located in the red and near-infrared regions, and the absorption and emission intensities are large, the application of phthalocyanine compounds as spectral probes is also very well-introduced, but the current applications are mainly for Biomolecules and alkali (earth) metal ions, phthalocyanine compounds as selective spectral probes for transition metal ions have not been reported, and phthalocyanine compounds with photodynamic anticancer activity and metal ion spectral probe functions are also very promising. Lack

Method used

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  • Ortho-positioned bridged azacrown ether modified phthalocyanin and preparation method and application thereof
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  • Ortho-positioned bridged azacrown ether modified phthalocyanin and preparation method and application thereof

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preparation example Construction

[0039] The preparation method of the ortho-bridged azacrown ether modified phthalocyanine shown in formula (1) of the present invention comprises the following steps:

[0040] (1) Preparation of bisphthalonitrile with the structure shown in the following formula:

[0041] ,

[0042] Using triethylene glycol and 3-nitrophthalonitrile as reactants, dimethyl sulfoxide as solvent, in the presence of potassium carbonate and under the protection of nitrogen, stir and react at room temperature ~ 45 ° C for 36 ~ 96 hours, through thin layer chromatography Monitor, terminate reaction when 3-nitrophthalonitrile is consumed substantially completely, purify target product by solvent method and recrystallization method; In the above-mentioned reaction, the feed molar ratio of triethylene glycol and 3-nitrophthalonitrile is 1:1.8~2.2, the amount of solvent needs 1~2ml for every mmol reactant 3-nitrophthalonitrile, and the consumption of potassium carbonate needs 1.5~3mmol for every mmol ...

Embodiment 1

[0060] The preparation and physical and chemical properties of ortho-bridged azacrown ether modified zinc phthalocyanine with the structure shown in formula (1):

[0061]

[0062] Formula 1)

[0063] Among them, M is Zn 2+ .

[0064] (1) Preparation of bisphthalonitrile with the structure shown in the following formula:

[0065]

[0066] With triethylene glycol (30mmol) and 3-nitrophthalonitrile (54~66mmol, preferably 60mmol) as reactants, with anhydrous DMSO as solvent (30~60ml, preferably 30ml), in potassium carbonate (80~ 180mmol, preferably 100mmol, added in batches) in the presence of nitrogen protection, stirred at room temperature to 45°C (preferably room temperature) for 48 to 96 hours, and monitored the end of the reaction by thin-layer chromatography. The reaction mixture was suction-filtered with a sand core funnel, the filtrate was collected, the filtrate was added to 500ml of ice-water mixture, stirred, a large amount of precipitate was precipitated, allo...

Embodiment 2

[0073] Preparation and properties of ortho-bridged azacrown ether modified zinc phthalocyanine with the structure shown in formula (2):

[0074]

[0075] Formula (2)

[0076] Among them, M is Zn 2+ .

[0077] Add 1.0 mmol of bisphthalonitrile obtained in Example 1, 2~5 mmol of phthalonitrile (preferably 4mmol) to 10~30ml (preferably 20ml) of n-pentanol (or N,N-dimethylformamide or dimethylethanolamine, preferably n-pentanol), nitrogen, stirred and heated to complete dissolution, then add 1~5 mmol (preferably 4mmol) anhydrous zinc acetate and 0.4~0.8ml (preferably 0.6ml) DBU, 130~ Stir the reaction at 150°C for 4-24 hours (monitor the end point of the reaction by thin-layer chromatography). After the solvent was removed by vacuum rotary evaporation, the reaction product was dissolved with a small amount of DMF, added to ice water, and the blue precipitate was collected by filtration, allowed to stand at 5°C, filtered with suction, washed with water, and freeze-dried to ob...

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Abstract

The invention discloses a ortho-positioned bridged azacrown ether modified phthalocyanin, and a preparation method and application thereof, and belongs to the field of optically functional material preparation. The compound provided by the invention has unique ortho-positioned bridged azacrown ether modification characteristic, and is clear in structure and unique in synthesis route. The compound provided by the invention is a multifunctional molecule which can be taken as both a photosensitive drug and a metal ion spectrum probe. As the photosensitive drug, the photosensitization ability of the compound is high; and as the spectrum probe, the compound can be used for selective identification to Fe<3+> and Cu<2+> ions.

Description

technical field [0001] The invention belongs to the field of preparation of photofunctional substances, and in particular relates to an ortho-bridged azacrown ether modified phthalocyanine and its preparation method and application. Background technique [0002] Phthalocyanine is an important class of functional materials, and has important applications in many fields such as photodynamic therapy, dyes, optical recording media, nonlinear optical materials, catalysts, and spectral probes. By introducing different substituents and central ions on the phthalocyanine ring, phthalocyanine compounds with different structural characteristics can be obtained, and phthalocyanine compounds with different structural characteristics may exhibit different properties. How to adjust substituents and central ions to obtain phthalocyanine compounds with a certain function or multiple functions at the same time is a very challenging task and requires a lot of creative exploration experiments....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/22A61K41/00A61K31/555A61K31/409G01N21/31A61P35/00A61P35/02A61P31/04A61P1/02A61P27/02A61P9/10A61P17/00A61P31/10
Inventor 黄剑东陈星伟柯美荣张妙芬
Owner FUZHOU UNIV
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