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Coumarin dye connected by diphenyl ethylene and its synthesis method and use

A technology of coumarin dyes and coumarins, applied in the direction of coumarin dyes, etc., can solve the problem of low two-photon absorption cross section, and achieve the effects of simple synthesis and separation methods, high yield, and convenient source of raw materials

Inactive Publication Date: 2009-03-18
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] An object of the present invention is to solve the problem of low two-photon absorption cross-section of common coumarin dyes, and provide a class of stilbene-linked coumarin dyes that have both high-efficiency photoinitiation efficiency and large two-photon absorption cross-section. Coumarin dyes

Method used

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  • Coumarin dye connected by diphenyl ethylene and its synthesis method and use
  • Coumarin dye connected by diphenyl ethylene and its synthesis method and use
  • Coumarin dye connected by diphenyl ethylene and its synthesis method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] A 1 、A 2 Synthesis of coumarin dyes (K1) with diethylamino groups

[0060] (1) Add 10 mmoles of 3-acetyl-7-diethylaminocoumarin, 20 mmoles of terephthalaldehyde and 50 ml of glacial acetic acid into a 100 ml three-necked flask, stir well, add 0.5 ml of hexahydropyridine, and heat Reflux at 120°C for 12 hours. After the reactant was cooled, it was filtered with suction, and the filter cake was washed with 10 ml of ethanol. The crude product was recrystallized twice with ethanol / acetonitrile (m / m=1:1) mixed solvent to obtain 3-[3-(4-formaldehyde)phenyl]acryloyl-7-diethylaminocoumarin intermediate body with a yield of 64.8%.

[0061] (2) 50 mmoles of potassium iodide, 50 mmoles of triphenylphosphine, 50 mmoles of diethylaniline, 3.75 g of 40% aqueous formaldehyde solution, 40 ml of chloroform, 20 ml of water, and 10 g of glacial acetic acid were mixed in a 250 ml round-bottomed flask, and kept at room temperature The mixture was stirred under low temperature for 3 wee...

Embodiment 2

[0064] Synthesis of Coumarin Dye (K2) Both A1 and A2 Are Methoxy

[0065] (1) Add 20mmol of 3-acetyl-7-methoxycoumarin, 50mmol of terephthalaldehyde and 90ml of glacial acetic acid into a 100ml three-necked flask, stir well, add 2ml of hexahydropyridine, and heat to 120 °C reflux for 25 hours. After the reactant was cooled, it was suction filtered, and the filter cake was washed with 10 ml of ethanol. The crude product was recrystallized twice with 30 ml of ethanol / acetonitrile (m / m=1:1) mixed solvent to obtain 3-[3-(4-formaldehyde)phenyl]acryloyl-7-methoxycoumarin Intermediate, yield 85.2%

[0066] (2) 10 millimoles of p-methoxybenzyl chloride and 10 millimoles of triphenylphosphine were added to a 100ml round-bottomed flask, and 30 milliliters of cyclohexane was added, heated to reflux for 2 hours, cooled to room temperature after the reaction, and pumped After filtering, the filter cake was washed with 15ml of ether to obtain the p-methoxybenzyl chlorophosphonate salt, w...

Embodiment 3

[0070] A 1 For dimethylamino, A 2 Synthesis of Diethylamino Coumarin Dye (K3)

[0071] (1) Add 20 mmoles of 3-acetyl-7-dimethylaminocoumarin, 50 mmoles of terephthalaldehyde and 50 ml of acetonitrile / ethanol mixed solvent with a volume ratio of 1:1 in a 100ml three-necked flask, stir After uniformity, add 1ml of acetic acid and 1ml of hexahydropyridine, and heat to reflux for 30 hours. After the reactant was cooled, it was filtered with suction, and the filter cake was washed with 8 ml of acetonitrile / ethanol mixed solvent. The crude product was recrystallized twice with ethanol / acetonitrile (m / m=1:1) mixed solvent to obtain 3-[3-(4-formaldehyde)phenyl]acryloyl-7-dimethylaminocoumarin intermediate body, yield 86.3%

[0072] (2) Mix 0.1 mole of potassium bromide, 0.1 mole of triphenylphosphine, 0.1 mole of diethylaniline, 37.5 g of 40% aqueous formaldehyde solution, 150 ml of chloroform, 100 ml of water, and 50 g of glacial acetic acid in a 500 ml round-bottomed flask. Aft...

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Abstract

The invention relates to two photon polymerization initiating system, especially relates to a high- effective method for synthesizing coumarins dyestuff connected with stilbene and its application in two photon polymerization. It comprises following steps: dissolving the mediate coumarins dyestuff with A1 gene into organic solvent; adding alkaline catalyst solution into it; dropping the organic phosphonic solvent carrying A2 gene with the same molar weight to that of coumarins dyestuff into reation system, heating to solvent boiling and refluxing; cooling and separting organic phase from water phase through extraction with organic solvent; drying and evaporating organic phase, separating coarse product with column chromatography, heating with iodine with its amount the same to that of catalyst, getting coumarins dyestuff connected with stilbene, which is used as photosensitiser in photon polymerization, and its structure is as follows: the substituents of A1 and A2 are the same or different, and are chose from alkyl, alkoxy, amido, heterocycle or substituted phenyl.

Description

field of invention [0001] The invention belongs to the field of two-photon polymerization initiating systems, and in particular relates to a high-efficiency synthesis method of stilbene-linked coumarin dyes and its application in two-photon polymerization. Background technique [0002] Two-photon polymerization technology is produced with the development of two-photon technology. It has the advantages of strong penetrating ability and high spatial resolution. Therefore, two-photon polymerization technology is used in mass information storage, fine processing of nanometer, micron and submicron structures , Photonic crystals and other fields have broad application prospects. For example, in 2001, the Kawata research group of Osaka University in Japan reported in the "Nature" magazine that the two-photon polymerization technology was used to process a three-dimensional calf with a height of 7 microns and a length of 10 microns (title: Fine processing of functionalized microdevi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/02
Inventor 吴飞鹏李雪施盟泉张云龙赵榆霞
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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