Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Ortho-bridged azacrown ether modified phthalocyanine and its preparation method and application

A technology of heterocrown ether and azine, which is applied in the field of preparation of photofunctional substances, can solve problems such as high absorption and emission intensity, lack of phthalocyanine compounds, and clinical application limitations, and achieve large molar absorption coefficient, good amphiphilicity, and improved The effect of transmittance

Active Publication Date: 2015-08-12
FUZHOU UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Ortho-bridged azacrown ether modified phthalocyanine and its preparation method and application
  • Ortho-bridged azacrown ether modified phthalocyanine and its preparation method and application
  • Ortho-bridged azacrown ether modified phthalocyanine and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
wavelengthaaaaaaaaaa
wavelengthaaaaaaaaaa
Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com