Naphthalimide compound fluorescent probe for recognizing Ag<+> in A549 and preparation method thereof
The technology of naphthalimide and fluorescent probe is applied in the field of fluorescent probe of metal ions, which can solve the problems of blocking the metabolic system and harm to the human body, and achieves the effects of high sensitivity, high response value and reliable detection method.
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Embodiment 1
[0036] Example 1: This example is a specific example prepared according to the reaction scheme of the compound of formula (I).
[0037] (2-Pyridinyl)-4-(2-pyrazinyl)-1.8-naphthalimide: In a 100 ml round-bottom flask equipped with a reflux condenser, successively add 1 mmol of 4-bromo-1,8-naphthalene Anhydride, 1 mmol 2-aminopyridine, 2 mmol sodium hydroxide and 2 mmol copper chloride in 20 ml of toluene, the reaction temperature was set at 115 °C. With Schlenk Line TechnologyN 2 The reaction was refluxed under the protection, and the reaction was monitored by TLC. After 17 h, the reaction was completed. After standing overnight at room temperature, a solid was precipitated, filtered, and then recrystallized with 40 ml of toluene to obtain compound (II) with a yield of 82%. Weigh compound (II) 1 mmol of N-(2-pyridyl)-4-bromo-1,8-naphthalimide, 1 mmol of 2-aminopyrazine, 2 mmol of cesium carbonate and excess iodide Cuprous in 20 ml of DMF. With Schlenk Line TechnologyN 2 Th...
Embodiment 2
[0040] Example 2: UV absorption spectrum of N-(2-pyridyl)-4-(2-pyrazinyl)-1.8-naphthalimide prepared in Example 1 (see figure 1 ) and fluorescence spectra (see Picture 1-1 ).
[0041] Accurately weigh N-(2-pyridyl)-4-(2-pyrazinyl)-1.8-naphthalimide, transfer it into a 10 mL volumetric flask, dissolve it with absolute ethanol, and determine when the sample is completely dissolved. volume, prepared to a concentration of 3.0×10 -5 mol·L -1 The solution was measured for its ultraviolet absorption spectrum and fluorescence excitation spectrum, respectively. The results are as figure 1 , Picture 1-1 shown; figure 1 is the ultraviolet absorption spectrum of silver ion fluorescent probe N-(2-pyridyl)-4-(2-pyrazinyl)-1.8-naphthalimide; Picture 1-1 This is the fluorescence spectrum of silver ion fluorescent probe N-(2-pyridyl)-4-(2-pyrazinyl)-1.8-naphthylimide for the detection of induced luminescence effect on aggregation.
[0042] from figure 1 It can be seen that the max...
Embodiment 3
[0043] Example 3: The N-(2-pyridyl)-4-(2-pyrazinyl)-1.8-naphthalimide fluorescent probe prepared in Example 1 was measured for Ag+ selectivity at an excitation wavelength of 650 nm .
[0044] Accurately weigh N-(2-pyridyl)-4-(2-pyrazinyl)-1.8-naphthalimide, dissolve it in chromatographic pure anhydrous ethanol, and configure the concentration to be 1.0×10 -4 mol·L -1 In the ligand solution of , 10 different metal ions (Zn 2+ , Hg + , Cu 2+ , Mg 2+ , Li + , Al 3+ , Ni + , K + , Ca 2+ , Ag + ), with a ligand concentration of 3.0×10 -5 mol·L -1 , the metal ion concentration is 1.0×10 -4 mol·L -1 The mixed solution was measured, and the change of the fluorescence spectrum of the solution was measured. The results are as figure 2 shown.
[0045] from figure 2 It can be seen that the fluorescence intensity of Ag+ is significantly stronger than that of other ions, indicating that the N-(2-pyridyl)-4-(2-pyrazinyl)-1.8-naphthylimide fluorescent probe has a hig...
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