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
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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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