Tetrazolium imine coumarins copper ion fluorescence probe and preparation method thereof
A technology of fluorescent probes and tetrazolium imines, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials. simple effect
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Embodiment 1
[0031] Example 1 : Synthesis of copper ion fluorescent probe 1-B, where R 1 is diethylamino, R 2 For hydrogen, n=2.
[0032]
[0033]
[0034] 5-Phenyl-1-H-tetrazole: Mix 515.6 mg (5 mmol) benzonitrile, 390 mg (6 mmol, 1.2 eq) NaN 3 , 818 mg (6 mmol, 1.2 eq) ZnCl 2Dissolved in 10 mL of water, stirred at 100°C, followed by TLC, the reaction was complete after 24 h, cooled, adjusted to pH=1 with 3M hydrochloric acid solution, filtered, and dried in vacuum to obtain 0.6 g of white solid with a yield of 82.1%.
[0035] 2-Acetonitrile-5-phenyltetrazole: 584.6 mg (4 mmol) 1-H-5-phenyltetrazole, 362.4 mg (4.8 mmol, 1.2 eq) chloroacetonitrile, 331.7 mg (2.4 mmol, 0.6 eq) K 2 CO 3 Dissolve in 8 mL of DMF, stir at 60°C, follow the reaction by TLC, complete the reaction after 12 h, cool to room temperature, dilute the reaction solution with 100 mL of dichloromethane, wash with 60 mL of water three times, and dry the organic phase with anhydrous sodium sulfate , stand still. ...
Embodiment 2
[0038] Example 2: Synthesis of copper ion fluorescent probe 2-B, where R 1 is diethylamino, R 2 is hydrogen, n=1.
[0039]
[0040] 1-A Operation method see embodiment 1.
[0041] Fluorescent probe 2-B (shown in the above formula): the molar ratio of 1-A to 2-aminomethylpyridine is 1:5, and the reaction time is 30 h. See 1-B for postprocessing. Yield 70%. 1 H NMR (500 MHz, CDCl 3 ): δ 8.61-8.55(d,1H),8.34-8.26(m,2H),8.13-8.04(s,1H),7.73-7.65(m,1H),7.65-7.53(m,3H),7.39- 7.31(m,1H),7.28-7.15(dd, 1H), 7.16-7.05(d, 1H), 6.53-6.46(m, 2H), 5.66-5.58(s, 2H), 4.44-3.36(q, 4H ), 1.20-1.16 (t, 6H).
Embodiment 3
[0042] Example 3: Synthesis of Copper Ion Fluorescent Probe 3-B, where R 1 is hydroxyl, R 2 For hydrogen, n=2.
[0043]
[0044] Please refer to Example 1 for the synthesis operation method of 5-phenyl-1-H-tetrazole and 2-acetonitrile-5-phenyltetrazole.
[0045] Compound 3-A (shown in the above formula): the molar ratio of 2-acetonitrile-5-phenyltetrazole to 4-hydroxysalicylaldehyde is 1:1.2, piperidine is the base catalyst, the reaction temperature is 80°C, and the reaction time is 10h. Refer to 1-A for the post-processing method, and the yield was 86%. 1 H NMR (500 MHz, DMSO): δ 11.13 (s, 1H), 8.77 (s, 1H), 8.21-8.07 (m, 2H), 7.76 (d, J = 8.6 Hz, 1H), 7.61 (dd, J = 4.9, 2.5 Hz, 3H), 6.94 (dd, J = 8.5, 2.2 Hz, 1H), 6.89 (d, J = 2.2 Hz, 1H).
[0046] Fluorescent probe 3-B (shown in the above formula): the molar ratio of 3-A to 2-aminoethylpyridine is 1:4, react at 80°C for 20 hours, refer to 1-B for the post-treatment method, and the yield is 60%. 1 H NMR (500 MHz, D...
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