Single\two-photon calcium ion fluorescent probe compound and preparation and application thereof
A calcium ion fluorescent probe and compound technology, used in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve problems such as increasing the difficulty of observing living biological samples, increasing thermal damage to biological samples, and achieving good selectivity, Good sensitivity and good biocompatibility
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Embodiment 1
[0028] Embodiment 1, the preparation method of calcium ion fluorescent probe compound, the steps are as follows:
[0029] Add BAPTA-CH to the three-necked bottle 3 -CHO 10g (15.87mmol), then weighed 4.5g (19.05mmol) of 4-methyl-N-methylpyridinium iodide salt, then poured 100mL of ethanol into it, added 2.5mL of piperidine dropwise, heated to 80 The reaction was refluxed at ℃ for 10 hours. After the reaction was stopped, the reaction solution turned dark red, and the precipitate was precipitated after cooling. It was filtered, rinsed with ethanol and water, dried and recrystallized in ethanol to obtain 11.6 g of the product.
[0030] The calcium ion fluorescent probe compound synthesized by the present invention, 1 H NMR (CDC1 3 ,400MHz,TMS)δ(ppm):8.54(d,J=7.2Hz,2H),8.03(d,J=6.8Hz,2H),7.25(m,4H),6.76(m,4H),4.21( m,20H),2.28(s,3H),1.94(s,3H),1.18(t,J=4.4Hz,12H).
[0031] The synthetic route of the described two-photon calcium ion fluorescent probe compound is as follows:
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Embodiment 2
[0033] Example 2. Two-photon solvent effect of calcium ion fluorescent probe compound.
[0034] The calcium ion fluorescent probe compound synthesized in Example 1 was formulated into a solution. Then its two-photon solvent effect was tested, and its two-photon absorption cross section and active absorption cross section in different solvents were calculated.
[0035] Weigh 0.0424g of the calcium ion fluorescent probe compound into a 5mL volumetric flask, and then dilute to the volume with chromatographically pure N,N-dimethylformamide (DMF) to obtain a concentration of 1×10 -2 mol / L probe stock solution. Then use a micro-sampler to take 500 μL of the mother liquor and put it into a 5mL capacity, and use chromatographically pure acetone, ethanol, DMF, acetonitrile, and water to make up a volume of 1×10 -4 mol / L solution, after shaking well, the laser pulse emitted by the Ti:sapphire Mira 900-F mode-locked laser was used as the irradiation light source, the repetition frequen...
Embodiment 3
[0040] Embodiment 3, performance experiment of calcium ion fluorescent probe compound on calcium ion
[0041] The calcium ion fluorescent probe compound synthesized in Example 1 was formulated into a solution. Its performance was then tested to determine its selectivity and sensitivity.
[0042] (1) Selectivity of calcium ion probe
[0043] Common metal ions may interfere with the detection of calcium ions, so it is necessary to determine whether the synthesized calcium ion probe has good selectivity in recognizing calcium ions.
[0044] in 1×10 -5 Add Cu(NO 3 ) 2 .3H 2 0, Fe(NO 3 ) 3 .9H 2 O, Zn(NO 3 ) 2 .6H 2 O, KNO 3 ,Mg(ClO 4 ) 2 .6H 2 O, NaClO 4 .H 2 O, AgNO 3 , AlCl 3 ·6H 2 O and other solids, so that the molar ratio of metal ions to compounds is 10:1. Then use a single-photon fluorescence detector to measure the fluorescence emission intensity, manually input the scanning wavelength range of 440~700nm, and the excitation wavelength of 419nm, the rel...
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