Rate type difunctional fluorescence molecular probe for detecting HSO4- ions, SO2 and derivatives thereof
A fluorescent molecular probe, SO2 technology, applied in the field of analytical chemistry, can solve the problems of difficult separation and purification, slow development of multifunctional probes, and high preparation costs
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Embodiment 1
[0030] Example 1 Synthesis of 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide.
[0031] Add 10 g (47.78 mmol) of 1,1,2-trimethyl-1H-benzo[e]indole and 8.94 g (57.34 mmol) of ethyl iodide in a 100 mL round bottom flask, 40 mL of acetonitrile, and load Reflux the condenser, heat and stir to reflux for 20 hours; cool the reaction solution to room temperature, filter, wash the filter cake with ether, and dry in vacuo to obtain 3-ethyl-1,1,2-trimethyl-1H-benzo[e ] Indol-3-ium iodide 14.6 g (83.7% yield).
Embodiment 2
[0032] Example 2 Synthesis of 3-ethyl-2-(4-hydroxystyryl)-1,1-dimethyl-1H-benzo[e]indol-3-ium iodide
[0033] Into a 25 mL round bottom flask was added 3.0 g (8.21 mmol) 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide and 1.2 g (9.86 mmol) Dissolve p-hydroxybenzaldehyde in 15 mL of absolute ethanol, add 3-4 drops of piperidine or pyrrolidine, and stir at room temperature for 12 hours; filter the reaction solution, wash with ethanol, and dry in vacuum to obtain the fluorescent molecular probe compound 2.98 of the present invention. g (77.2% yield). 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.55 - 8.43 (d, J = 16.1Hz, 1H), 8.43 - 8.37 (d, J = 8.5 Hz, 1H), 8.31 - 8.25 (d, J = 9.0 Hz, 1H),8.24 - 8.18 (d, J = 8.2 Hz, 1H), 8.18 - 8.12 (d, J = 8.8 Hz, 2H), 8.11 - 8.03(d, J = 8.9 Hz, 1H), 7.83 – 7.76 (ddd, J = 8.4, 6.9, 1.3 Hz, 1H), 7.73 - 7.66(t, J = 7.5 Hz, 1H), 7.54 - 7.40 (d, J = 16.1 Hz, 1H), 7.00 - 6.89 (d, J =8.4 Hz, 2H), 5.10 - 4.48 (q, J = 7.2 Hz, 2H), 2.2...
Embodiment 3
[0034] Example 3 Dual-functional probes in the detection of HSO 4 - Applications in ions.
[0035] Spectral property experiment of fluorescent molecular probes according to the present invention: dissolving the probes in dimethyl sulfoxide (DMSO) to configure 1 mM probe solutions, and configuring 1 mM NaHSO respectively 4 aqueous solution and Na 2 SO 3 Aqueous solution, and 10 mM interfering ion aqueous solution, all tests are tested at room temperature with a volume ratio of organic phase to aqueous phase of 8:2, the organic phase is dimethyl sulfoxide (DMSO) with 1 mM probe solution and detection The ethanol added at the time, the water phase is HSO 4 - and SO 2 Aqueous solution and deionized water added during detection. The specific test method is: take 20 μL of 1 mM probe solution, 1580 μL of analytical pure ethanol, 20 μL of 1mM NaHSO 4 Water solution and 380 μL deionized water solution were placed in a 2 mL sample tube, and the changes in UV absorption and fluor...
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