Fluorescent probe for detecting hydrogen peroxide and hypochlorite, synthetic method and application
A synthesis method and fluorescent probe technology, applied in chemical instruments and methods, fluorescence/phosphorescence, material analysis through optical means, etc., can solve the problems of fluorescence emission interference, complex synthesis, etc., achieve high sensitivity, simple synthesis, highly selective effect
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Embodiment 1
[0029] Preparation of Compound 1
[0030] Compound 2 (382mg, 1mmol), compound 3 (445mg, 1.5mmol) and K 2 CO 3 (207mg, 1.5mmol) was dissolved in 10mL acetonitrile, and refluxed for 12 hours. After the reaction was completed, it was spin-dried, and column chromatography (petroleum ether: ethyl acetate = 1:8) gave 430 mg of a white product (compound 1). rate of 72%. The reaction scheme is as follows:
[0031]
[0032] Its NMR spectrum is as Figure 1-2 shown. 1 H NMR (400MHz, CDCl 3 )δ (ppm): 8.34 (s, 1H), 8.08 (d, 1H, J = 8.0Hz), 7.87 (t, 3H, J = 8.0Hz), 7.53 (d, 3H, J = 8.0Hz), 7.48 (t, 1H, J=8.0Hz), 7.42(d, 2H, J=8.0Hz), 7.36(t, 2H, J=8.0Hz), 7.23(d, 2H, J=8.0Hz), 5.35(s ,2H),1.364(s,3H); 13 C NMR (100MHz, CDCl 3 )δ (ppm): 162.1, 156.2, 151.9, 138.7, 138.0, 136.2, 135.9, 135.2, 132.4, 131.6, 129.3, 128.3, 127.0, 126.8, 126.0, 124.8, 123.6, 122.9, 121.8, 141.3 71.2, 24.9.
[0033] Preparation of Compound 2
[0034] Compound Ⅰ (277mg, 1mmol), compound Ⅱ (125mg, 1m...
Embodiment 2
[0038] Probe compound 1 was dissolved in N,N-dimethylformamide to configure 1.0×10 -3mol / L solution, take the probe solution and add DMF and PBS (pH=7.4) buffer to prepare a 10 μmol / L (DMF / PBS=9:1, V / V) solution for use.
[0039] Firstly, the fluorescence change of compound 1 in response to hypochlorite was tested, and its excitation was at 375nm. Depend on image 3 It can be seen that the probe has no fluorescence without the addition of hypochlorite, which is due to the fact that the hydroxyl group is protected and the ESIPT in the probe molecule is blocked. After adding hypochlorite, the probe has obvious emission at 450nm peak, and with the increase of hypochlorite concentration (0-80μmol / L), the emission peak at 450nm is gradually enhanced, which may be due to the oxygen atom of the probe molecule being oxidized, and the ICT process appears in the molecule, and its linear range 0-80μmol / L, the detection limit is 9.1×10 -9 mol / L.
[0040] Then, the response of compound...
Embodiment 3
[0042] The effect of pH value change on the fluorescence intensity of probe compound 1
[0043] In order to investigate the effect of pH value on the detection of hypochlorite by compound 1, the fluorescence intensity changes before and after the interaction between probe compound 1 and hypochlorite were tested under different pH conditions, and the excitation was at 375nm. Depend on Figure 5 It can be seen that (a represents that hypochlorite is not added, and b represents that hypochlorite is added), when the hypochlorite of 50 μmol / L is added and the pH is 5-7, the fluorescence intensity of the solution at 501nm is constantly enhanced, and the pH is 7.4-11 When , the fluorescence intensity of the solution at 450nm reaches the maximum and remains unchanged, indicating that compound 1 has a better response performance to hypochlorite under physiological pH conditions.
[0044] With the above conditions unchanged, CTAB was added to test the fluorescence change of compound 1 ...
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