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A kind of near-infrared second region heptamethine dye and preparation method thereof

A technology of near-infrared and cyanine dyes, applied in the direction of methine/polymethine dyes, organic dyes, chemical instruments and methods, etc., can solve the problems of complex synthesis process, long absorption wavelength, low quantum yield, etc., and achieve molar extinction High coefficient, mild synthesis conditions, and good photostability

Active Publication Date: 2022-01-11
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the heptamethine dye has the characteristics of long absorption wavelength, small background interference, and small Raman scattering interference, it is easy to aggregate, has low quantum yield, complex synthesis process, and poor stability.

Method used

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  • A kind of near-infrared second region heptamethine dye and preparation method thereof
  • A kind of near-infrared second region heptamethine dye and preparation method thereof
  • A kind of near-infrared second region heptamethine dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] (1) Weigh 0.85 g of 1,8-naphtholactam, 0.56 g of KOH in a 100 ml flask, add 10 ml of N-methylpyrrolidone, stir the mixture at 90°C for 30 min, then weigh 0.75 g of 1, 4-Butane sultone was added thereto, and the mixture was stirred at 90° C. for 10 h. After the reaction was completed, it was cooled, and 35 ml of acetone was added, and a yellow solid precipitated out. After suction filtration, the filter cake was washed with acetone for 3 times and then vacuum-dried to obtain a pure and pure benzindole derivative 1-(4-sulfonylbutyl)-1,2-dihydrobenzindole potassium salt with a yield of 90 %.

[0055] (2) Weigh 1.5 grams of 1-(4-sulfonylbutyl)-1,2-dihydrobenzindole potassium salt obtained in step 1 and dissolve 1.51 grams of tetrabutylammonium chloride in 8 milliliters of acetic acid , stirred at 90°C for 1 h, after the reaction was completed, dichloromethane was added dropwise thereto, the precipitate was removed by filtration, and the obtained solvent was concentrated by...

Embodiment 2

[0061] (1) Weigh 0.68 g of 1,8-naphtholactam, 0.56 g of KOH in a 100 ml flask, add 10 ml of N-methylpyrrolidone, stir the mixture at 90°C for 30 min, then weigh 0.82 g of 1, 4-Butane sultone was added thereto, and the mixture was stirred at 90° C. for 10 h. After the reaction was completed, it was cooled, and 35 ml of acetone was added, and a yellow solid precipitated out. After suction filtration, the filter cake was washed with acetone for 3 times and then vacuum-dried to obtain a pure and pure benzindole derivative 1-(4-sulfonylbutyl)-1,2-dihydrobenzindole potassium salt with a yield of 95 %.

[0062] (2) Weigh 1.5 grams of 1-(4-sulfonylbutyl)-1,2-dihydrobenzindole potassium salt obtained in step 1 and dissolve 1.64 grams of tetrabutylammonium chloride in 8 milliliters of acetic acid , stirred at 90°C for 1 h, after the reaction was completed, dichloromethane was added dropwise thereto, the precipitate was removed by filtration, and the obtained solvent was concentrated by...

Embodiment 3

[0067] (1) Weigh 0.75 g of 1,8-naphtholactam, 0.56 g of KOH in a 100 ml flask, add 10 ml of N-methylpyrrolidone, stir the mixture at 90°C for 30 min, then weigh 0.75 g of 1, 4-Butane sultone was added thereto, and the mixture was stirred at 90° C. for 10 h. After the reaction was completed, it was cooled, and 35 ml of acetone was added, and a yellow solid precipitated out. Suction filtration, the filter cake was washed with acetone for 3 times and then vacuum-dried to obtain the pure benzindole derivative 1-(4-sulfonylbutyl)-1,2-dihydrobenzindole potassium salt with a yield of 92% .

[0068] (2) Weigh 1.5 grams of 1-(4-sulfonylbutyl)-1,2-dihydrobenzindole potassium salt obtained in step 1 and dissolve 1.55 grams of tetrabutylammonium chloride in 8 milliliters of acetic acid , stirred at 90°C for 1 h, after the reaction was completed, dichloromethane was added dropwise thereto, the precipitate was removed by filtration, and the obtained solvent was concentrated by rotary evapo...

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Abstract

The invention discloses a heptamethine dye QHS-Cy in the second near-infrared region and a preparation method thereof, belonging to the field of organic dye synthesis. The prepared QHS-Cy has a symmetrical chemical structure and is purple to black solid in appearance. The heptamethine dye QHS-Cy in the second near-infrared region prepared by the present invention has an ultraviolet absorption wavelength of 983nm in dichloromethane, a fluorescence emission wavelength of 1018nm, good photostability, high photothermal efficiency, and can effectively avoid biological background Fluorescence interference and short synthesis steps are of great significance in the application research of heptamethine dyes.

Description

technical field [0001] The invention relates to the technical field of organic dye synthesis, in particular to a heptamethine dye in the second near-infrared region and a preparation method thereof. Background technique [0002] Near-infrared fluorescent dyes have great application value in analytical chemistry, life science, environmental science, optical materials and so on. In the fields 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. Designing and synthesizing novel fluorescent dyes in the second near-infrared region has become a hot research topic in recent years. [0003] Although the heptamethine dye has the characteristics of long absorption wavelength, small background interference, and small Raman scattering interference, it is easy to aggregate, has low quantum yield, complex synthesis process, and poor stability. Contents of the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/08C09K11/06
CPCC09B23/086C09K11/06C09K2211/1029
Inventor 闫立峰钱红云
Owner UNIV OF SCI & TECH OF CHINA