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O-hydroxyl-imidogen containing all-conjugated visible light sensitizer with Y-shaped structure and synthesis thereof

An ortho-hydroxyl and visible light technology, applied in the preparation of imino compounds, organic chemistry, etc., can solve the problem of rare photosensitizers

Inactive Publication Date: 2013-11-13
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to further expand the dendritic structure of visible photosensitizers, increase the possibility of chemical modification, and expand their application range, it is necessary to introduce dendritic structures into the molecular skeleton of visible photosensitizers, but due to the challenges of chemical construction, there are not many such photosensitizers. See

Method used

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  • O-hydroxyl-imidogen containing all-conjugated visible light sensitizer with Y-shaped structure and synthesis thereof
  • O-hydroxyl-imidogen containing all-conjugated visible light sensitizer with Y-shaped structure and synthesis thereof
  • O-hydroxyl-imidogen containing all-conjugated visible light sensitizer with Y-shaped structure and synthesis thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (4,4’-bis((2”-hydroxy-phenyl-methyl-imino)-styryl))-triphenylamine

[0021] Mix 4,4'-bis((4"-amino)-styryl)-triphenylamine (5mmol, 2.395g) with o-hydroxy-benzaldehyde (10mmol, 1.22g, 1.04ml) in a three-necked glass bottle , with 50ml of ethanol as solvent, magnetic stirring at room temperature for 10 hours to end the reaction, spin-drying under reduced pressure to obtain the crude product, using benzene as the eluent, and separating the pure product with silica gel chromatography column. The yield is 50%, and the melting point: 275~ 277°C. Its 1 The H NMR spectrum is as figure 1 as shown, 1 H-NMR (D 1 -CDCl 3 ,500MHz)δ(ppm):13.319(s,-OH,2H),8.670(s,N=CH,2H),7.563-7.550(d,Ar-H,4H),7.428-7.399(t,Ar- H, 8H), 7.308-7.294 (d, Ar-H, 6H), 7.159-6.951 (m, Ar-H, 11H; CH=CH, 4H).

[0022] The preparation concentration is 1×10 -5 mol·l -1 Ethyl acetate solution of (4,4'-bis((2"-hydroxy-phenyl-methyl-imino)-styryl))-triphenylamine, using UV-visible spectrometer, scanning 20...

Embodiment 2

[0024] The preparation concentration is 1×10 -5 mol·l -1 (4,4'-bis((2"-hydroxy-4''-(N,N-dimethyl)-phenyl-methyl-imino)-styryl))-triphenylamine acetic acid Ethyl ester solution, using a UV-visible spectrometer, scans the UV-visible absorption spectrum of 200nm~600nm. Its UV-visible absorption spectrum is as follows image 3 As shown, the maximum absorption wavelength is 445nm, and the absorption peak extends to 520nm.

Embodiment 3

[0026] The preparation concentration is 1×10 -5 mol·l -1 (4,4'-bis((2"-hydroxy-4''-(N,N-diethyl)-phenyl-methyl-imino)-styryl))-triphenylamine acetic acid Ethyl ester solution, using a UV-visible spectrometer, scans the UV-visible absorption spectrum of 200nm~600nm. Its UV-visible absorption spectrum is as follows Figure 4 As shown, the maximum absorption wavelength is 476nm, and the absorption peak extends to 550nm.

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Abstract

The invention provides an o-hydroxyl-imidogen containing all-conjugated visible light sensitizer with a Y-shaped structure. The chemical general formula of the o-hydroxyl-imidogen containing all-conjugated visible light sensitizer is as shown in the specification, wherein R in the structural formula represents H, N(CH3)2, N(CH2CH3)2 or N(CH2CH2CH2CH3)2. The synthesis of the o-hydroxyl-imidogen containing all-conjugated visible light sensitizer comprises the following steps of: adding a diamino-triphenylamine derivative and an o-hydroxyl-benzaldehyde derivative to a three-neck glass bottle, wherein the mol ratio of the diamino-triphenylamine derivative to the o-hydroxyl-benzaldehyde derivative is 1: 2; by taking ethanol by a volume which is 40-100 times of the volume of the o-hydroxyl-benzaldehyde derivative as a solvent, magnetically stirring at normal temperature for 10 hours, and then finishing reaction; separating and purifying the mixture after the reaction, thereby obtaining the o-hydroxyl-imidogen containing all-conjugated visible light sensitizer with the Y-shaped structure. Tested by an ultraviolet-visible light spectrometer, the o-hydroxyl-imidogen containing all-conjugated visible light sensitizer with the Y-shaped structure has excellent absorption effect in the visible region.

Description

technical field [0001] The invention relates to the field of organic photosensitizers, in particular to the synthesis and synthesis of fully conjugated visible photosensitizers containing o-hydroxyl-imine groups with a Y-shaped structure. Background technique [0002] Due to their superior photochemical properties, organic photosensitizers are widely used in many fields such as biological imaging, material science, and chemical engineering. In order to further expand the dendritic structure of visible photosensitizers, increase the possibility of chemical modification, and expand their application range, it is necessary to introduce dendritic structures into the molecular skeleton of visible photosensitizers, but due to the challenges of chemical construction, there are not many such photosensitizers. See. Contents of the invention [0003] The object of the present invention is to overcome the deficiency of the above-mentioned background technology, and synthesize a clas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07C249/02
Inventor 高放陆瑶马慧莹丁戈李红茹
Owner CHONGQING UNIV
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