Distyrene near ultraviolet photosensitizer comprising dihydroxyl-imino segment and synthesis method thereof

A stilbene-based, near-ultraviolet light technology, applied in the preparation of imino compounds, organic chemistry, etc., can solve the problems of rare near-ultraviolet photosensitizers, difficult to control the chemical composition of near-ultraviolet photosensitizers, etc.

Inactive Publication Date: 2013-10-09
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, stilbene-based near-ultraviolet photosensitizers are widely used in materials science, biomedicine, and chemical engineering, and the maximum wavelength of most stilbene-based near-ultraviolet photosensitizers is either below 300nm or above 380nm ; Because the chemical composition of the near-ultraviolet photosensitizer is difficult to control, the stilbene-based near-ultraviolet photosensitizer with the maximum absorption wavelength at 350nm to 380nm is rare

Method used

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  • Distyrene near ultraviolet photosensitizer comprising dihydroxyl-imino segment and synthesis method thereof
  • Distyrene near ultraviolet photosensitizer comprising dihydroxyl-imino segment and synthesis method thereof
  • Distyrene near ultraviolet photosensitizer comprising dihydroxyl-imino segment and synthesis method thereof

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Embodiment 1

[0020] 2,4-bis(2'-hydroxy-phenyl-methyl-imino)-stilbene:

[0021] Mix 2,4-diamino-stilbene (5mmol, 1.05g) and 2-hydroxy-benzaldehyde (10mmol, 1.22g, 1.04ml) in a three-necked glass bottle, use 50ml ethanol as solvent, and stir magnetically at room temperature After 10 hours, the reaction was terminated, and the crude product was obtained by spin-drying under reduced pressure. Using cyclohexane as the eluent, the purified product was separated by silica gel chromatography. Yield: 75%, melting point: 162.6-163.8°C. That 1 The H NMR spectrum is as figure 1 as shown, 1 H-NMR (D 6 -DMSO,500MHz)δ(ppm):13.058(s,-OH,1H),13.005(s,-OH,1H),9.110(s,N=CH,1H),9.046(s,N=CH,1H ),7.945-7.928(d,Ar-H,1H),7.751-7.733(m,Ar-H,1H),7.686-7.668(m,Ar-H,1H),7.571-7.502(m,Ar-H , 4H), 7.485-7.393 (m, Ar-H, 5H), 7.363-7.280 (m, CH=CH, 2H), 7.053-6.986 (m, Ar-H, 4H).

[0022]

[0023] The preparation concentration is 1×10 -5 mol·l -1 The ethyl acetate solution of 2,4-bis(2'-hydroxy-phenyl-methyl...

Embodiment 2

[0025] 2,4-Bis(2’’-hydroxy-phenyl-methyl-imino)-4’-methoxy-stilbene

[0026] Mix 2,4-diamino-(4'-methoxy)-stilbene (5mmol, 1.05g) and 2-hydroxy-benzaldehyde (10mmol, 1.22g, 1.04ml) in a three-necked glass bottle, Using 50ml of ethanol as a solvent, magnetically stirred at room temperature for 10 hours to complete the reaction, spin-dried under reduced pressure to obtain a crude product, and used cyclohexane as an eluent to separate with a silica gel column to obtain a pure product. Yield: 75%, melting point: 137.0-139.0°C. That 1 The H NMR spectrum is as figure 2 as shown, 1 H-NMR (D 6 -DMSO,500MHz)δ(ppm):13.095(s,Ar-OH,1H),13.076(s,Ar-OH,1H),9.111(s,N=CH,1H),9.044(s,N=CH ,1H),7.912-7.896(d,Ar-H,1H),7.746-7.732(d,Ar-H,1H),7.682-7.669(d,Ar-H,1H),7.516-7.426(m,Ar -H,6H),7.412-7.226(m,CH=CH,2H),7.054-6.981(m,Ar-H,6H),3.784(s,O-CH 3 ,3H).

[0027]

[0028] The preparation concentration is 1×10 -5 mol·l -1 The ethyl acetate solution of 2,4-bis(2''-hydroxy-phenyl-methy...

Embodiment 3

[0030] 2,4-Bis(2’’-hydroxy-phenyl-methyl-imino)-3’,4’-dimethoxy-stilbene

[0031] Put 2,4-diamino-(3',4'-dimethoxy)-stilbene (5mmol, 1.35g) and 2-hydroxy-benzaldehyde (10mmol, 1.22g, 1.04ml) in a three-mouth glass Mix in a bottle, use 50ml of ethanol as solvent, and magnetically stir at room temperature for 10 hours to end the reaction, spin dry under reduced pressure to obtain a crude product, use cyclohexane as an eluent, and separate with a silica gel chromatography column to obtain a pure product. Yield: 75%, melting point: 153.5-155.0°C. That 1 The H NMR spectrum is as image 3 as shown, 1 H-NMR (D 6 -DMSO,500MHz)δ(ppm):13.191(s,-OH,1H),13.101(s,-OH,1H),9.102(s,N=CH,1H),9.060(s,N=CH,1H ),7.893-7.876(d,Ar-H,1H),7.744-7.729(d,Ar-H,1H),7.681-7.666(d,Ar-H,1H),7.526-7.524(d,CH=CH ,1H),7.484-7.423(m,Ar-H,4H),7.269-7.236(d,Ar-H,1H),7.197-7.194(d,CH=CH,1H),7.107-7.090(d,Ar -H,1H),7.046-6.982(m,Ar-H,5H),3.827(s,O-CH 3 ,3H),3.782(s,O-CH 3 ,3H).

[0032]

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Abstract

The invention relates to a distyrene near ultraviolet photosensitizer comprising a dihydroxyl-imino segment. The chemical formula of the photosensitizer is shown in the specification, wherein R1 and R2 are H or OCH3. The synthetic steps are as follows: adding a 2,4-diamido-distyrene derivative or 2-hydroxyl-benzaldehyde into a three-mouth glass bottle, wherein the molar ratio of 4-diamido-distyrene derivative to 2-hydroxyl-benzaldehyde is 1:2; on the basis of taking ethanol as a solvent of which the volume is 30-60 times of that of 2-hydroxyl-benzaldehyde, magnetically stirring for reaction for 10 hours at normal temperature; after reaction, decompressing and spinning the mixture to obtain a coarse product; on the basis of taking cyclohexane as an eluant, separating by a silica gel chromatographic column to obtain the distyrene near ultraviolet photosensitizer comprising the dihydroxyl-phenyl-imino segment. Through test by an ultraviolet-visible spectrograph, the photosensitizer has good absorption in a near ultraviolet area from 350nm to 380nm.

Description

technical field [0001] The invention relates to the field of organic photosensitizers, in particular to stilbene-based near-ultraviolet photosensitizers containing bishydroxyl-imine moieties and their synthesis. Background technique [0002] At present, stilbene-based near-ultraviolet photosensitizers are widely used in materials science, biomedicine, and chemical engineering, and the maximum wavelength of most stilbene-based near-ultraviolet photosensitizers is either below 300nm or above 380nm ; Because the chemical composition of the near-ultraviolet photosensitizer is difficult to control, the stilbene-based near-ultraviolet photosensitizer with the maximum absorption wavelength at 350nm-380nm is rare. Contents of the invention [0003] The purpose of the present invention is to overcome the above-mentioned deficiencies in the background technology, and synthesize a class of stilbene-based near-ultraviolet photosensitizers containing bishydroxyl-imine segments. [000...

Claims

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Application Information

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