A kind of preparation method and application of bifluoroboron fluorescent dye responsive to triethylamine
A fluorescent dye and triethylamine technology, which is applied in the direction of luminescent materials, organic dyes, azo dyes, etc., can solve the problems of long reaction time, complicated operation method of triethylamine, low sensitivity, etc., and achieve fast detection and stable peak value change , the effect of low fluorescence intensity
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Embodiment 1 Embodiment 1
[0023] Example 1 Example 1 Synthesis of Probe Molecules
Embodiment 1-1
[0025] Take compound 1 (598 mg, 2 mmol); salicylaldehyde (1.96 ml, 2 mmol), TsOH (34.2, mg, 0.2 mmol) were dissolved in DCM (60 ml), stirred at 35 ° C for 12 h, and the reaction was monitored by spot plate until the raw materials were completely reacted, After neutralization with alkali, the product was washed with water, extracted, dried, rotary evaporated, and purified by filtration to obtain compound 3 (216 mg, yield 26.7%). Take the above compound 3 (202mg, 0.5mmol), add 20ml dichloromethane solution, 1.00ml triethylamine, under electromagnetic stirring, slowly add boron trifluoride ether solution (1.00ml) dropwise, raise the temperature to 35 ℃ , refluxed for 30 min, TLC spot plate detection, the product was washed with water, extracted, dried, rotary evaporated, filtered and purified to obtain compound I as a golden yellow solid (194 mg, yield 86%).
[0026]
Embodiment 1-2
[0028] Take compound 1 (598 mg, 2 mmol); salicylaldehyde (1.96 ml, 2 mmol), TsOH (17.1, mg, 0.1 mmol), dissolve in DCM (60 ml), stir at 35 ° C for 12 h, and monitor the reaction by spotting until the raw materials are completely reacted, After neutralization with alkali, the product was washed with water, extracted, dried, rotary evaporated, and purified by filtration to obtain compound 3 (299 mg, yield 37%). Take the above compound 3 (202mg, 0.5mmol), add 20ml dichloromethane solution, 1.00ml triethylamine, under electromagnetic stirring, slowly add boron trifluoride ether solution (1.00ml) dropwise, raise the temperature to 35 ℃ , refluxed for 30 min, TLC spot plate detection, the product was washed with water, extracted, dried, rotary evaporated, filtered and purified to obtain compound I as a golden yellow solid (198.4 mg, yield 88%). Compared with Example 1-1, the amount of p-toluenesulfonic acid was reduced by half, and the yield of compound 3 was increased by 10.3%.
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