Fluorescent probe molecules and preparation method and application thereof
A fluorescent probe and molecule technology, applied in the field of fluorescent probe molecules and their preparation, can solve problems such as unreported, and achieve the effects of short response time, large on-off ratio, and good specificity and selectivity
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Embodiment 1
[0068] Synthesis of terphenyl dibromo derivatives (formula as follows):
[0069]
[0070] Add 974.5 mg (2 mmol) of 1,4-dibromo-2,5-diiodobenzene, 609.5 mg (5 mmol) of phenylboronic acid, and 115.6 mg (0.1 mmol) of tetrakis(triphenylphosphine)palladium into a 100 mL two-necked bottle, and pump Vacuum the nitrogen for three times, inject 20 mL of anhydrous and oxygen-free tetrahydrofuran and 10 mL (2 mol / L) of potassium carbonate aqueous solution, reflux at 74 ° C for 8 h, extract with DCM after the reaction is completed, and wash the organic phase with anhydrous sodium sulfate for three times. After drying, filtering, spin-drying, and column separation and purification with pure petroleum ether, a white powder of 2,5-dibromo-1,4-diphenylbenzene was obtained with a yield of 63.7%, namely the intermediate product 1. Product characterization data are as follows:
[0071] 1 H NMR (400MHz, CDCl 3 ): δ(TMS,ppm)7.64(s,2H),7.44(m,10H).13C NMR(100MHz,CDCl 3 ): δ (TMS, ppm) 142.95...
Embodiment 2
[0086] Example 2 The time response of fluorescent probe molecules to hydrazine
[0087] Add 1 mL of aqueous solutions with different hydrazine contents (the concentration of fluorescent probe molecules is 10 μM) to 9 mL of fluorescent probe molecules / dimethyl sulfoxide solution, so that the equivalent ratios are 1:0.1, 1:0.3 and 1:0.5, respectively. Test Fluorescence spectra of fluorescence intensity changing with time (0 to 15 minutes) under the three conditions, see figure 1 ,Depend on figure 1 It can be seen that after hydrazine is mixed with the fluorescent probe molecule, the fluorescence intensity increases with time, indicating that the fluorescent probe molecule has a fluorescence-enhanced response to the detection of hydrazine and the detection reaction can be completely completed within 3 minutes.
Embodiment 3
[0088] Embodiment 3 Fluorescent probe molecule is to the concentration response of hydrazine
[0089] Add 1 mL of aqueous solutions with different hydrazine contents (the concentration of fluorescent probe molecules is 10 μM) to 9 mL of fluorescent probe molecule / DMSO solution, so that the equivalent ratio of hydrazine to fluorescent probe molecules is between 0 and 2. Shake the oscillator for three seconds, measure the fluorescence curve after 15 minutes, see respectively figure 2 , 3 ,Depend on figure 2 It can be seen that the fluorescence intensity gradually increases with the increase of hydrazine content. image 3 It can be seen that the fluorescence enhancement reaches saturation when the equivalent ratio of hydrazine to fluorescent probe molecules is 1:1, indicating that 1 equivalent of hydrazine can completely react with 1 equivalent of probe molecules. figure 2 , 3 All indicate that the fluorescent probe molecule has a high sensitivity to the detection of hydra...
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