Near-infrared two-zone squaric acid quinoline dye and preparation method thereof

A squaraine quinoline, near-infrared technology, applied in organic dyes, chemical instruments and methods, methine/polymethine dyes, etc., can solve the problems of poor stability, low quantum yield, complex synthesis process, etc. Low effect, simple synthesis method and high molar extinction coefficient

Inactive Publication Date: 2019-07-12
NANTONG UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to provide a kind of quinoline dye of near-infrared second region and its preparation method, to solve the problems of low quantum yield of organic small molecule near-infrared second region dye in the prior art, complex synthesis process, poor stability and the like

Method used

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  • Near-infrared two-zone squaric acid quinoline dye and preparation method thereof
  • Near-infrared two-zone squaric acid quinoline dye and preparation method thereof
  • Near-infrared two-zone squaric acid quinoline dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Weigh 0.5 g of 6-bromo-4-methylquinoline into a 50 ml flask, and add 20 ml of dry acetonitrile. After dissolving, 0.308 g of bromobutane was added, and the mixture was heated and refluxed at 70° C. to react for 6 hours. After the reaction was completed, most of the acetonitrile was removed by distillation under reduced pressure, the product was dropped into anhydrous ether, and a yellow solid was precipitated. After suction filtration, the filter cake was washed with anhydrous ether for 3 times to obtain a pure quinoline compound with a yield of 95%.

[0031] 1 H NMR (400MHz, CDCl 3 )δ(ppm)9.66(1H,d),8.68(1H,d),8.28(1H,d),8.15(1H,d),7.85(1H,d),5.56(2H,t),4.15(2H ,m),3.32(3H,s),1.79(2H,m),1.36(3H,t).ESI-MScalculated for C 14 H 17 BrN:278.05found:301.02[M+Na] + .

[0032] (2) 1 gram of malononitrile was weighed and dissolved in 50 ml of benzene. After being dissolved, 2.83 grams of diethyl squaraine was slowly added dropwise, and 1.67 grams of triethylamine was...

Embodiment 2

[0038](1) Weigh 0.5 g of 6-bromo-4-methylquinoline into a 50 ml flask, and add 20 ml of dry acetonitrile. After being dissolved, 0.414 g of iodobutane was added, and the mixture was heated and refluxed at 70° C. to react for 6 hours. After the reaction was completed, most of the acetonitrile was removed by distillation under reduced pressure, the product was dropped into anhydrous ether, and a yellow solid was precipitated. After suction filtration, the filter cake was washed with anhydrous ether for 3 times to obtain a pure product quinoline compound with a yield of 90%.

[0039] (2) 1 gram of malononitrile was weighed and dissolved in 50 ml of benzene, 2.83 grams of diethyl squaraine was slowly added dropwise after being dissolved, and 2.9 grams of triethylamine was added after the dropwise addition was completed. The solution was reacted at room temperature for 12 hours. After the reaction was completed, the solution was evaporated to dryness, and 10 ml of benzene was add...

Embodiment 3

[0042] (1) Weigh 0.5 g of 6-bromo-4-methylquinoline into a 50 ml flask, and add 20 ml of dry acetonitrile. After dissolving, 0.5 g of bromooctane was added, and the mixture was heated and refluxed at 70° C. to react for 6 hours. After the reaction was completed, most of the acetonitrile was removed by distillation under reduced pressure, the product was dropped into anhydrous ether, and a yellow solid was precipitated. After suction filtration, the filter cake was washed with anhydrous ether for 3 times to obtain a pure quinoline compound with a yield of 92%.

[0043] (2) 1 gram of malononitrile was weighed and dissolved in 50 ml of benzene, 2.83 grams of diethyl squaraine was slowly added dropwise after being dissolved, and 2.9 grams of triethylamine was added after the dropwise addition was completed. The solution was reacted at room temperature for 12 hours. After the reaction was completed, the solution was evaporated to dryness, and 10 ml of benzene was added for recrys...

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Abstract

The invention discloses a near-infrared two-zone squaric acid quinoline dye and a preparation method thereof, and belongs to the field of organic dye synthesis. The prepared squaric acid quinoline dyeis of a symmetrical chemical structure, looks like a brown to black solid, has a melting point of 200 to 400 DEG C. The R alkyl group is a C1-C8 alkyl chain, and changing the length of the R alkyl chain does not affect the wavelength of fluorescence and can meet different use requirements, so that the dye is applied more widely. The near-infrared two-zone squaric acid quinoline dye prepared by the preparation method has a fluorescence emission wavelength of 900 to 1,100 nm, a high molar extinction coefficient, good light stability, can effectively avoid biological background fluorescence interference, has the advantages of high fluorescence quantum yield, short synthesis steps and the like, has excellent penetrability to the environment and biological tissues, and provides a good application prospect for biomolecular markers, solar cells, fluorescent imaging and the like.

Description

technical field [0001] The invention relates to a near-infrared second-region fluorescent dye, belonging to the field of organic dye synthesis, in particular to a near-infrared second-region squaraine quinoline dye and a preparation method thereof. Background technique [0002] Near-infrared fluorescent dyes have great application value in analytical chemistry, life science, environmental science, and optical materials. In the field of medicine and biology, near-infrared fluorescent probes, especially near-infrared second-region fluorescent probes, are a safe, high-precision, and non-invasive detection method. Design and synthesis of novel near-infrared second-region fluorescent dyes has become a hot research topic in recent years. Squaric acid quinoline dyes are fluorescent dyes with various substituted quinoline compounds as end groups and squaraine as the core. The molecules of squaraine dyes contain a symmetrical electron resonance system, and electron-donating or elec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/18C09B23/10C09K11/06
CPCC07D215/18C09B23/0066C09B23/105C09K11/06C09K2211/1029C09K2211/1007
Inventor 王琦弓瑾吴铭敏朱晓霞顾心亮张颖
Owner NANTONG UNIVERSITY
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