Near-infrared carbon rhodamine fluorescent dye and synthetic method thereof
A technology for fluorescent dyes and synthesis methods, which is applied in the field of near-infrared carborhodamine fluorescent dyes and their synthesis, can solve the problems of difficult synthesis of carborhodamine, and achieve the effects of good water solubility, high quantum yield, and simple synthesis steps
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[0047] Example 1, Synthesis of near-infrared carbon rhodamine fluorescent dye CR1, using intermediate 5-1 to synthesize CR1.
[0048] The first step is the synthesis of 2,7-dinitroanthracene-9,10-dione
[0049] Dissolve anthrone (3.90 g, 20 mmol) in 25 ml fuming nitric acid at 0-5°C in an ice bath, stir and react for 2 hours, warm to room temperature and continue the reaction for 2 hours, then pour into 70 ml glacial acetic acid, A bright yellow precipitate separated out after standing overnight. After suction filtration, the filter cake was recrystallized with glacial acetic acid to obtain the light yellow solid compound 2,7-dinitroanthracene-9,10-dione (2.98 g, 10 mmol) with a yield of 50%. 1 H-NMR (DMSO-d 6 , 600MHz) δ (ppm): 8.84 (d, J=2.4Hz, 1H); 8.71 (d, J = 2.4Hz, 2H); 8.49 (d, J = 9.0 Hz, 2H).
[0050] The second step is the synthesis of 2,7-diaminoanthracene-9,10-dione
[0051] Dissolve sodium hydroxide (2.15 g, 53.5 mmol) in 80 ml of water, add sodium sulfide nonahydrate (5...
Example Embodiment
[0061] In Example 2, the synthesis of the near-infrared carbon rhodamine fluorescent dye CR7, the intermediate 4-1 was used to synthesize CR7.
[0062] The first to fourth steps are the same as in Example 1.
[0063] The fifth step, synthesis of the near-infrared carbon rhodamine fluorescent dye CR7
[0064] Dissolve 2-methylbromobenzene (0.51 g, 3 mmol) in 10 ml dry tetrahydrofuran, cool the temperature to -78℃ in the acetone liquid nitrogen bath, and then add dropwise n-butyllithium solution (2.4mol / L THF solution, 0.5 ml), the reaction is stirred for 1 hour. Add dropwise a tetrahydrofuran solution (5ml) containing 2,7-bis(dimethylamino)-9-hydroxy-9-methyl-anthracene-10-one (93 mg, 0.3 mmol), and slowly return to room temperature (25 ℃), react for 2 hours, then acidify with 2 mol / L dilute hydrochloric acid, the solution turns from yellow to blue-green. The reaction solution was extracted 3 times with dichloromethane, the organic phases were combined, dried with anhydrous sodium ...
Example Embodiment
[0066] In Example 3, the synthesis of the near-infrared carbon rhodamine fluorescent dye CR9, the intermediate 4-2 was used to synthesize CR9.
[0067] The first to third steps are the same as in Example 1.
[0068] The fourth step is the synthesis of 2,7-bis(dimethylamino)-9-hydroxy-9-phenyl-anthracene-10-one (Intermediate 4-2)
[0069] 2,7-Bis(dimethylamino)anthracene-9,10-dione (0.10 g, 0.33 mmol) was dissolved in 10 ml of dry tetrahydrofuran, and then phenyl magnesium bromide (1mol / L of THF Solution, 1 ml), stir the reaction at room temperature for 30 minutes, and then quench the reaction with dilute hydrochloric acid solution. Add 50 ml of water to the reaction solution, extract 3 times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, spin off the solvent and separate by column chromatography to obtain the yellow solid compound 2,7-bis(dimethylamino) )-9-hydroxy-9-phenyl-anthracene-10-one (80 mg, 0.23 mmol), yield 70%. 1 H-NMR (CDCl 3 , 600M...
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