Imidazopyridine rhodamine hydrazide copper ion ratiometric fluorescent probe and its application
A ratiometric fluorescent probe, rhodamine hydrazide technology, applied in fluorescence/phosphorescence, luminescent materials, material analysis by optical means, etc., can solve the problem of less ratiometric fluorescent probes, and achieve strong resistance to other ions interference , the effect of enhanced fluorescence intensity and high sensitivity
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Embodiment 1
[0015] Embodiment 1: The synthesis scheme of the compound of formula (1) is shown in the following formula:
[0016]
[0017] Concrete synthetic steps are as follows:
[0018] In a 50 mL round bottom flask, add 0.253 g (1.0 mmol) imidazo[1,5-a]pyridinecarboxylic acid, 0.290 g (1.5 mmol) 1-(3-dimethylaminopropyl)-3-ethyl Carbodiimide (EDC), 0.180g (1.5 mmol) 4-dimethylaminopyridine (DMAP), 20 mL of anhydrous dichloromethane, react at room temperature for 30 minutes, then add 0.470g (1.0 mmol) rhodamine hydrazide , reacted at room temperature for 10 hours. After the reaction was detected by TLC, 100 mL of dichloromethane was added, washed three times with 30 mL of water, the dichloromethane layer was dried over sodium sulfate, concentrated, and column chromatography gave 0.48 g of an off-white solid with a yield of 68.2%.
[0019] H NMR spectrum determination: 1 H NMR (400 MHz, CDCl 3 ): δ7.95 (m, 1H), 7.72 (dd, J =4.0 Hz, 8.0 Hz, 1H), 7.51-7.46 (m, 3H), 7.10-7.08 (m, 1...
Embodiment 2
[0021] To formula (1) compound (10 -5 M) were added 2 equivalents of Cr in the ethanol solution 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Cu 2+ ,Zn 2+ ,Cd 2+ ,Hg 2+ and Ag + After measuring the change in the ratio of fluorescence emission intensity at 470nm and 580nm, it was found that: the compound of formula (1) has 2+ Has a unique fluorescence selectivity, adding 1 equivalent of Cu 2+ After that, the fluorescence intensity of compound 1 at 470nm was significantly reduced, and at the same time, the fluorescence intensity at 580nm was significantly enhanced, I 580 / I 470 = 13.99, such as figure 2 shown.
Embodiment 3
[0023] In formula (1) compound (10 -5 M) and 1 equivalent of Cu 2+ 2 equivalents of Mg were added to the ethanol solution 2+ , Ca 2+ , Al 3+ ,Sn 2+ , Pb 2+ ,Cr 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Zn 2+ ,Cd 2+ ,Pd 2+ ,Hg 2+ and Ag + After measuring the change in the ratio of fluorescence emission intensity at 470nm and 580nm, it was found that the compound of formula (1) has strong anti-interference ability to other ions, such as image 3 shown.
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