A kind of rhodamine fluorescent dye excited by 532nm and its preparation method
A fluorescent dye and fluorescent quantum yield technology, applied in the field of rhodamine-based fluorescent dyes and their preparation, can solve the problems of difficult synthesis, complex structure, rare species and the like, and achieve the effects of high reaction yield and simple synthesis steps
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Embodiment 1
[0037] Synthesis of target dyes RHO-1
[0038] Synthesis of intermediate 4
[0039]
[0040] 1 g of 5-hydroxyquinoline was dissolved in 30 ml of dried tetrahydrofuran solution, and 1.7 g of hexahydrogenic acid nickel is added, stirring at room temperature, a small amount of 1 g of sodium borohydride was added in the reaction system. After stirring at room temperature overnight, 5 ml of deionized water was stirred for 10 min, poured into a mixture of 100 mL: 200 mL of dichloromethane and water, extracted, collecting an organic phase, sodium sulfate, dried over, filtration, filtrate removal solvent The solid was 840 mg, and the yield was 82%. Its nuclear magnetic spectrum graph hydrogen spectrum data is as follows:
[0041] 1 H NMR (400MHz, CDCL 3 Δ6.83 (t, j = 8.0 Hz, 1H), 6.13 (D, J = 1.5 Hz, 1H), 6.11 (D, J = 1.6 Hz, 1H), 4.62 (S, 1H), 3.99 (S, 1H), 3.26 (DD, J = 7.1, 3.8 Hz, 2H), 2.65 (T, J = 6.6 Hz, 2H), 1.97 (DD, J = 6.6, 5.5, 4.4 Hz, 2H).
[0042] Synthesis of intermediate ...
Embodiment 2
[0056] Synthesis of target dye RHO-2
[0057] Synthesis of intermediate 6
[0058]
[0059] 1 g of 5-hydroxyquinoline was dissolved in 30 ml of dried tetrahydrofuran solution, and 1.7 g of hexahydrogenic acid nickel is added, stirring at room temperature, a small amount of 1 g of sodium borohydride was added in the reaction system. After stirring at room temperature overnight, 5 ml of deionized water was stirred for 10 min, poured into a mixture of 100 mL: 200 mL of dichloromethane and water, extracted, collecting an organic phase, sodium sulfate, dried over, filtration, filtrate removal solvent The solid was 871 mg, and the yield was 85%.
[0060] 1 H NMR (400MHz, CDCL 3 Δ6.81 (D, J = 8.1 Hz, 1H), 6.12 (DD, J = 8.1, 2.5 Hz, 1H), 6.01 (D, J = 2.4 Hz, 1H), 3.46 (S, 1H), 3.29 ( T, J = 5.7, 2H), 2.70 (T, J = 6.4 Hz, 2H), 1.93 (TD, J = 11.4, 6.3Hz, 2H)
[0061] Synthesis of target dye RHO-2
[0062]
[0063] A 5-hydroxy tetrahydroquinoline and 215 mg of intermediate 5 were weighed...
Embodiment 3
[0069] Synthesis of target dyes RHO-3
[0070] Synthesis of intermediate 7
[0071]
[0072] 1 g of 4-hydroxy tetrahydroquinoline was taken in 15 ml of acetic acid, and a slow amount of sodium borohydride was slowly added, stirred for 30 min, slowly added acetaldehyde solution. After stirring at room temperature for 2 h, the reaction was stopped. Most of the acetic acid was removed under reduced pressure, quenched with aqueous sodium carbonate solution, adjusted pH to neutral, ethyl acetate extraction, washing and dried, remove most of the solvent, silica gel column is separated, the eluent is an oil ether: ethyl acetate = 50: 1 (volume ratio) to obtain 1.09 g of orange solid, yield 93%. Its nuclear magnetic spectrum graph hydrogen spectrum data is as follows:
[0073] 1 H NMR (400MHz, CDCL 3 Δ6.82 (D, J = 8.0Hz, 1H), 6.24 (S, 1H), 6.12 (D, J = 8.0 Hz, 1H), 3.33 (Q, J = 7.1 Hz, 2H), 3.28 (T, J = 5.7 Hz, 2H), 2.70 (T, J = 6.4 Hz, 2H), 2.02-1.91 (m, 2H), 1.18 (T, J = 7.1 Hz, 3H). ...
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