Calcium ion fluorescence probe based on aggregation induced effect, preparation method and uses thereof

[0029] Example 1: Synthesis of probe

[0030] In order to understand the present invention more clearly, the following further describes the present invention in detail through specific embodiments. 4-Hydroxybenzophenone (1.98 g, 10 mmol) and potassium carbonate (4.14 g, 30 mmol) were added to 50 mL of acetone solution, followed by slowly adding 1-bromo-2-chloroethane (1.43 g) at room temperature , 10 mmol). The mixture was heated to reflux for 8 h, and then filtered. The filtrate was concentrated and recrystallized from methanol to obtain compound 2 as a white solid with a yield of 70%.

[0031] 1 H NMR (400 MHz, CDCl 3 ), δ (ppm): 7.83 (d, J = 8.7Hz, 2H); 7.76 (d, J = 7.5Hz, 2H); 7.58 (d, 1H); 7.47 (m, J = 6.9Hz, 2H); 6.98 (d, J = 6.8Hz, 2H); 4.38 (t, J = 7.5Hz, 2H); 3.69 (t, J = 7.5Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ), δ(ppm): 195.86, 162.21, 139.46, 133.07, 132.48, 130.18, 128.91, 128.63,114.46, 68.42, 29.05. ESI-MS: m / z calc’d for C 15 H 13 ClO 2 : [M+Na] + 326.9996;fo

[0038] Example 2: Determination of ion selectivity by probe

[0039] Use DMSO / HEPES buffer (10 mM, 1:99 v / v) as the solvent to accurately configure the probe with a concentration of 20 μM, respectively mix the solution with 5 times the equivalent of various metal ions, and measure its excitation wavelength at 340 nm Fluorescence emission spectrum under the measurement result as figure 1 Shown. It can be seen that the probe is only for Ca 2+ Shows obvious selective response, no obvious response to other ions, especially to Mg 2+ There is no obvious response signal.

[0040] Example 3: Determination of the anti-interference ability of the probe

[0041] Use DMSO / HEPES buffer (10 mM, 1:99 v / v) as the solvent to accurately configure the concentration of the 20 μM probe solution, and first mix with 5 times the equivalent of Ca 2+ Mix the solution with 5 times the equivalent of various interfering ions, and measure the fluorescence emission spectrum at the excitation wavelength of 490 nm. The measurement results are as follows figure 2 . Of which 1: Ca 2+ ; 2: Na + ; 3: K + ; 4: Ag + ; 5:Mg 2+ ; 6: Al 3+ ; 7: Cr 3+ ; 8: Mn 2+ ; 9: Fe 2+ ; 10: Fe 3+ ; 11: Co 2+ ; 12: Ni 2+ ; 13: Cu 2+ ;14: Zn 2+ ; 15: Cd 2+ ; 16: Ba 2+ ; 17: Hg 2+ ; 18: Pb 2+ . It can be seen that in addition to Cu 2+ , Co 2+ , Fe 2+ And Fe 3+ In addition to a certain degree of fluorescence quenching due to its paramagnetism and strong coordination effect, the probe is very sensitive to Ca 2+ The measurement is basically not interfered by other coexisting ions.