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Novel indolenium squaraine cyanine dye containing quinazolinone structure

A kind of technology of quinoxalinone and squaraine, applied in the field of novel near-infrared absorption squaraine dyes

Inactive Publication Date: 2004-07-14
NO 63971 TROOPS PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the research on such dyes, the maximum absorption wavelength of many compounds is limited to below 840nm, which is mainly because the emission wavelength of most of the semiconductor lasers currently used is generally located at 680-840nm, so the near-infrared absorption corresponding to this band There are many studies on dyes, but there are relatively few studies on squaraine dyes with wavelengths above 840nm

Method used

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  • Novel indolenium squaraine cyanine dye containing quinazolinone structure
  • Novel indolenium squaraine cyanine dye containing quinazolinone structure
  • Novel indolenium squaraine cyanine dye containing quinazolinone structure

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Experimental program
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Effect test

Embodiment 1

[0069] 3.20g (0.02mol) 3-methyl-2 (1H)-1,4-quinoxalin-2-one and 1.14g (0.01mol) squaraine are placed in the mixed solvent of 20ml n-butanol and 60ml benzene, Stir and reflux for 8 hours under the catalysis of a small amount of pyridine, and the water generated in the reaction is separated with a Dean-Stark water separator. Cool at room temperature, filter, and wash with benzene and petroleum ether successively to obtain a dark green powder product with metallic luster, namely compound [1].

Embodiment 2

[0071] Put 3.76g (0.02mol) of 1-ethyl-3-methyl-2(1H)-1,4-quinoxalin-2-one and 1.14g (0.01mol) of squaric acid in 40ml of n-propanol and 40ml of toluene In the mixed solvent, stirred and refluxed for 24 h under the catalysis of a small amount of pyridine, and the water generated in the reaction was separated with a Dean-Stark water separator. Cool at room temperature, filter, and wash with benzene, a small amount of ethanol, and petroleum ether successively to obtain a dark green powder product with metallic luster, that is, compound [2].

Embodiment 3

[0073] Put 5.62g (0.02mol) 1-phenyl-3-methyl-6-nitro-2(1H)-1,4-quinoxalin-2-one and 1.14g (0.01mol) squaraine in 40ml In a mixed solvent of isobutanol and 40ml of benzene, stirred and refluxed for 48h under the catalysis of a small amount of quinoline, the water generated in the reaction was separated with a Dean-Stark water separator. Cool at room temperature, filter, and wash with benzene and petroleum ether successively to obtain a dark green product, compound [3].

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Abstract

The present invention relates to a new kind of infrared absorbing squaraine cyanine dye as one new kind of compound containing quinoxalinone heterocycle in its structure. It has absorption wavelength of 700-1100 nm. It is prepared through condensation of squaric acid and quinoxalinone as precursor compound. It may be used in laser protection, fluorescent labeling, photoelectronic functional material and other fields.

Description

Technical field [0001] The invention relates to a novel near-infrared absorbing squaraine dye, which contains a quinoxalinone heterocycle in its structure and can be applied to the fields of laser protection, fluorescent marking, photoelectric functional materials and the like. Background technique [0002] Since Cohen S. et al first reported the synthesis of a new compound squaraine in J.A.C.S. of the American Chemical Society in 1959, a large number of squaraine dyes have been obtained by condensing it with active groups of other compounds. The research and development of this kind of squaraine dye is very rapid, and many patents and literatures have reported its new application value and potential application direction, such as being used as a sensitizing dye, a photochromic compound for an erasable disc, a disposable Permanently writeable optical storage materials, photosensitizers in photodynamic therapy, fluorescent labeling dyes, laser protection dyes, and infrared ab...

Claims

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Application Information

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IPC IPC(8): C09B25/00
Inventor 杨小兵丁松涛王安邦杨裕生
Owner NO 63971 TROOPS PLA
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