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Coumarin dyestuff linked by naphthene ketones, method for synthesis and use thereof

A technology of cycloalkane ketone and coumarin, which is applied in the field of visible light sensitizing dyes, can solve the problem of wide absorption band coverage and achieve the effect of wide absorption band

Inactive Publication Date: 2007-07-25
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] One of the purposes of the present invention is to solve the problem of absorbing long-wavelength lasers that ordinary coumarin dyes do not have, and the problem of wide coverage of the absorption band, and provide a class of lasers that have both long absorption wavelengths and wide wavelength coverage. , a cycloalkanone-linked coumarin dye that matches the wavelength of commonly used visible lasers

Method used

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  • Coumarin dyestuff linked by naphthene ketones, method for synthesis and use thereof
  • Coumarin dyestuff linked by naphthene ketones, method for synthesis and use thereof
  • Coumarin dyestuff linked by naphthene ketones, method for synthesis and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] Synthesis of Coumarin Dyes Linked by Cyclopentanone (CP-COU)

[0113] (1) 40 millimoles of cyclopentanone and 10 millimoles of p-dimethylaminobenzaldehyde are put into a flask, add 7 milliliters of dehydrated alcohol and 10 milliliters of water, add dropwise 0.5 milliliters of 10wt% NaOH aqueous solution, After reacting at room temperature at 25°C for 5 hours, the orange precipitate was filtered and separated by column chromatography with 0.2wt% ethanol / chloroform to obtain half-p-dimethylaminobenzylidene cyclopentanone dye with a yield of 85%.

[0114](2) (synthetic method refers to literature "Journal of Medicinal Chemistry" 1983 volume 31 page 3014, ChemPharm Bull, 1983,31,3014) with 10 mmoles of 4-methyl-5-pyrrolylcoumarin, 12 mmoles Put selenous acid in a flask, add 50 ml of xylene to heat and dissolve, reflux for 10 hours, heat filter to remove gray-black selenium, leave the filtrate to cool and precipitate yellow needle-like crystals, and filter to obtain pure 4-...

Embodiment 2

[0117] Synthesis of Coumarin Dye Linked by Cyclohexanone (CHE-COU)

[0118] (1) Put 30 millimoles of cyclohexanone and 10 millimoles of acetaldehyde into a flask, add 20 milliliters of absolute ethanol and 5 milliliters of water, drop 2 milliliters of hexahydropyridine, and react at 60 ° C for 24 hours, The orange precipitate was filtered and separated by column chromatography with 0.2wt% ethanol / chloroform to obtain half 2-ethylcyclohexanone dye with a yield of 75%.

[0119] (2) (synthetic method refers to the literature "Journal of Medicinal Chemistry" 1983, volume 31, page 3014, ChemPharm Bull, 1983, 31, 3014) 10 millimoles of 3-methyl-7-methoxycoumarin, 15 millimoles Put molar selenous acid in a flask, add 60 milliliters of ethanol to heat and dissolve, reflux for 15 hours, heat filter to remove gray-black selenium, leave the filtrate to cool and precipitate yellow needle-like crystals, and filter to obtain pure 3-aldehyde -7-Methoxycoumarin, yield 93%.

[0120] (3) Plac...

Embodiment 3

[0122] Synthesis of Coumarin Dye Linked by Cycloheptanone (CHP-COU)

[0123] (1) Put 20 millimoles of cycloheptanone and 10 millimoles of benzaldehyde into a flask, add 20 milliliters of absolute ethanol and 2 milliliters of water, add dropwise 3 milliliters of 10 wt % KOH aqueous solution, and react at 65 ° C for 36 hours , filtered the orange precipitate, and separated by column chromatography with 0.2wt% ethanol / chloroform to obtain a hemibenzylidene cycloheptanone dye with a yield of 65%.

[0124] (2) (synthetic method refers to literature "Acta Medicinal Chemistry" 1983 volume 31 page 3014, ChemPharm Bull, 1983,31,3014) 10 mmoles of 3-methyl-6-phenylcoumarin, 18 mmoles Put selenous acid in a flask, add 70 ml of acetonitrile to heat and dissolve, reflux for 24 hours, heat filter to remove gray-black selenium, leave the filtrate to cool and precipitate yellow needle-like crystals, and filter to obtain pure 3-aldehyde- 6-Phenylcoumarin, yield 90%.

[0125] (3) Place the ab...

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Abstract

The invention provides a coumarin dyestuff linked by naphthene ketones, method for synthesis and use, wherein the method employs the conventional hydroxyaldehyde condensation reaction and consists of, charging naphthene ketone, corresponding aldehydes with A1 groups into reactor, obtaining semi-naphthene ketone dyestuff with A1 groups, subjecting corresponding third position methyl substituted or fourth position methyl substituted coumarin having A2 group and selenious acid in another catalyst case to obtain coumarin aldehyde having A2 group, subjecting the A1 group semi-naphthene ketone dyestuff and A2 group coumarin aldehydes to reaction at the presence of mixed solvent of dimethylbenzene and alcohol, thus obtaining coumarin type dyestuffs coupled by naphthene ketones.

Description

field of invention [0001] The invention belongs to the field of visible light-sensitizing dyes, in particular to a class of coumarin dyes linked by cycloalkane ketones and a synthesis method and application thereof. Background technique [0002] In recent years, lasers with visible wavelengths such as Ar + (488nm, 514nm), YAG (532nm), He-Ne (633nm) lasers are widely used in the fields of holographic recording, laser direct plate making, photocuring and laser stereolithography. important area of ​​research. Whether it is the direct photosensitization mechanism of the polymerization initiator or the dye-sensitized polymerization initiator mechanism, the synthesis of efficient visible light-sensitized dyes is an effective way to increase the speed of photopolymerization initiation and improve the properties of materials. Coumarin dye is a very fast-response laser dye, in which 7-aminocoumarin dye, as an electron donor, can effectively sense visible light and obtain a higher p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/08C07D311/06C09B57/02
Inventor 吴飞鹏王涛李妙贞王尔鉴
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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