A kind of fluorescent compound and its preparation method and use
A technology of fluorescent compounds and fluorescent probes, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, fluorescence/phosphorescence, etc. High efficiency and good photostability
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Embodiment 1
[0037] A kind of preparation of fluorescent compound, its synthetic route is as follows figure 1 , the specific preparation method is:
[0038] S1: Add 4-hydroxy-benzo[b]thiophene-7-carboxaldehyde (40mg, 0.33mmol), ethyl benzindole (80.5mg, 0.33mmol) into a 250mL three-necked flask, and then add 150mL of The mixed solution of n-butanol / toluene (7:3, V / V) was stirred and dissolved. The reaction system was heated to reflux for 3.5h, during which the progress of the reaction was monitored by thin-layer chromatography;
[0039] S2: After the reaction, the solvent was removed in vacuo, the crude product was placed in a mixed system of water and dichloromethane to separate layers, and the organic phase was kept, and the operation was repeated three times. The crude product was further purified by silica gel column chromatography, and the eluent was ethyl acetate / methanol (3:1, V / V). The finally obtained product Cy5-M is an orange solid with a yield of 86%. 1H NMR (400MHz, DMSO):...
Embodiment 2
[0043] A kind of preparation of fluorescent probe, its synthetic route is as follows Figure 4 Shown, the specific preparation method is:
[0044] The Cy5-M (17.2 mg, 5 mmol) obtained in Example 1 was dissolved in 15 mL of pyridine. Phosphorus oxychloride (10 μL, 5 mmol) was then added dropwise to the mixed solution. After stirring at room temperature for 0.5 h, 5 mL of water was added to the reaction system to continue stirring for 0.5 h. Finally the solvent was removed using a rotary evaporator. The obtained crude product was extracted in a mixture of dichloromethane and water. The aqueous phase was retained and concentrated under reduced pressure. The product was purified by a reverse-phase silica gel C18 column (mobile phase: 75% methanol / water, injection volume 15 μL; column Eclipse XDB-C18 (9.4 mm×250 mm, 5 μm); elution rate 2 mL / min;). The probe CyP was obtained as a yellow oil with a yield of 72%. 1 H NMR (400MHz, DMSO): δ11.42(s, 2H, -OH), 8.99(d, 1H, Ar-H), 8.5...
Embodiment 3
[0050] A kind of preparation of fluorescent compound:
[0051] S1: Add 4-hydroxy-benzo[b]thiophene-7-carboxaldehyde (40mg, 0.33mmol), ethyl benzindole (85mg, 0.33mmol) into a 250mL three-necked flask, and then add 155mL of n- The mixed solution of butanol / toluene (7:2.5, V / V) was stirred and dissolved. The reaction system was heated to reflux for 3.2h, during which the progress of the reaction was monitored by thin-layer chromatography;
[0052] S2: After the reaction, the solvent was removed in vacuo, the crude product was placed in a mixed system of water and dichloromethane to separate layers, and the organic phase was kept, and the operation was repeated three times. The crude product was further purified by silica gel column chromatography, and the eluent was ethyl acetate / methanol (3:1, V / V). The final product Cy5-M is an orange solid with a yield of 82.3%.
[0053] A kind of preparation of fluorescent probe:
[0054] The obtained Cy5-M (18 mg, 5 mmol) was dissolved ...
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