Ratiometric fluorescent molecular probe for detecting hypochlorite ion, preparation method and application thereof
A fluorescent probe, ratiometric technology, applied in the field of chemical fluorescent materials, can solve the problem of less ClO-specific detection, and achieve remarkable effects and strong selectivity
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Embodiment 1
[0067] (1) Synthesis of compound 1:
[0068] A mixture of 5.0g (28.4mmol) of 7-hydroxy-4-methylcoumarin and 9.2g (65mmol) of hexamethylenetetramine was dissolved in glacial acetic acid (55mL), heated to 90°C and stirred at reflux for 5.5h. Then hydrochloric acid (20 mL) was added dropwise to the solution, and the reaction solution was heated for 50 min under the same conditions. After the reaction was cooled, ice-cold water (100 mL) was added to the solution, extracted with ether several times, and dried by rotary evaporation to obtain a crude product, which was washed with Al 2 o 3 The crude product was purified by column chromatography (petroleum ether:dichloromethane=10:1). After rotary evaporation and drying, a light yellow solid was obtained, that is, compound 1 (0.84 g in total), with a yield of 14.5%.
[0069] Compound 1 1 H NMR picture as figure 1 Shown: 1 H NMR(400MHz,DMSO)δ(ppm):11.86(s,1H),10.38(s,1H),7.88(d,1H),6.92(d,1H),6.26(d,1H),2.33(d ,3H). After verifi...
Embodiment 2
[0088] (1) Synthesis of compound 1:
[0089] A mixture of 1.0 g of 7-hydroxy-4-methylcoumarin and 7.2 g of hexamethylenetetramine was dissolved in glacial acetic acid (40 mL), heated to 80° C. and stirred at reflux for 6.5 h. Then hydrochloric acid (10 mL) was added dropwise to the solution, and the reaction solution was heated for 60 min under the same conditions. After the reaction was cooled, ice-cold water (100 mL) was added to the solution, extracted with ether several times, and dried by rotary evaporation to obtain a crude product, which was washed with Al 2 o 3 The crude product was purified by column chromatography (petroleum ether:dichloromethane=10:1). After rotary evaporation and drying, a light yellow solid was obtained, that is, compound 1 (0.84 g in total).
[0090] (2) Synthesis of Compound 2:
[0091] Weigh 0.56 g of 4-bromo-1,8-naphthalic anhydride and 0.35 g of 2-aminoethylmorpholine and dissolve them in absolute ethanol (10 mL), then heat the reaction s...
Embodiment 3
[0097] (1) Synthesis of compound 1:
[0098] A mixture of 10.0g 7-hydroxy-4-methylcoumarin and 11.2g hexamethylenetetramine was dissolved in glacial acetic acid (70mL), heated to 100°C and stirred at reflux for 4h. Then hydrochloric acid (30 mL) was added dropwise to the solution, and the reaction solution was heated for 40 min under the same conditions. After the reaction was cooled, ice-cold water (100 mL) was added to the solution, extracted with ether several times, and dried by rotary evaporation to obtain a crude product, which was washed with Al 2 o 3 The crude product was purified by column chromatography (petroleum ether:dichloromethane=10:1). After rotary evaporation and drying, a pale yellow solid, Compound 1, was obtained.
[0099] (2) Synthesis of Compound 2:
[0100] Weigh 1.67g of 4-bromo-1,8-naphthalic anhydride and 0.95g of 2-aminoethylmorpholine and dissolve in absolute ethanol (30mL), then heat the reaction solution to 80°C under reflux and stir for 3h. ...
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