A kind of preparation method and application of perylene diimide pH fluorescent probe
A perylene diimide and fluorescent probe technology is applied in the field of preparation of perylene diimide pH fluorescent probes, which can solve the problem of large limitations in the use of cell detection, inability of fluorescent probes to probe, poor measurement accuracy, etc. problem, to achieve the effect of good application prospect, obvious color change of solution and not easy to decompose
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Embodiment 1
[0025] Dibromo-substituted perylene diimide derivatives (91.2mg, 0.1mmol), 4-ethynylaniline (28.08mg, 0.24mmol), CuI (3mg, 0.015mmol) were dissolved in triethylamine (10mL), in Add Pd(PPh under argon atmosphere 3 ) 4 (17.33mg, 0.015mmol), reacted under reflux until the raw material point disappeared. It was extracted with dichloromethane and water, dried over anhydrous sodium sulfate, and the solvent was spin-dried under reduced pressure, and dichloromethane-petroleum ether (v / v=4:1) was used as the eluent to pass through a silica gel column. Yield 30 mg (yield: 30%) 1 H-NMR (600MHz, CDCl 3 , ppm): δ10.17(t, J=10.5Hz, 2H), 8.79(m, 4H), 7.48(d, J=7.5Hz, 4H), 6.74(d, J=8.3Hz, 4H), 5.21 (s, 2H), 4.03 (s, 4H), 2.28 (m, 4H), 1.86 (m, 4H), 1.36-1.21 (m, 32H), 0.83 (t, J=6.9Hz, 12H). Compound I 1 H-NMR as attached figure 1 shown.
Embodiment 2
[0027] Accurately weigh 1.0 mg of compound I, dissolve it in 1.02 ml of chloroform, and obtain the mother solution of the probe, and the concentration of the solution is 1×10 -3 mol / L. Dissolve trifluoroacetic acid in acetonitrile to prepare solutions with different pHs, accurately draw a certain amount of probe mother liquor and add them to the above solutions respectively, so that the final concentration of probe (I) is 1×10 -5 mol / L. Measure the fluorescence emission intensity of probe I solutions with different pH values by fluorescence spectrophotometer (attached figure 2 ). From attached figure 2 It can be clearly seen that at pH > 2.3, the probe solution has almost no fluorescence. As the pH decreases, the fluorescence intensity of the fluorescent probe begins to increase gradually.
Embodiment 3
[0029] Fluorescent probe I was dissolved in chloroform and prepared as a detection solution with a concentration of 1×10 -3 mol / L; the probe was added to pH=1.3 solution (left) and trifluoroacetic acid acetonitrile solution at pH=2.3 (right), the final concentration of probe I was 1×10 -5 mol / L, as attached Figure 4 shown; fluorescence images were taken under fluorescent lamp illumination.
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