A fluorescent probe for detecting zinc ions and pH, its preparation method and application
A fluorescent probe and detection kit technology, applied in the field of fluorescent probe compounds of zinc ion and pH, can solve the problems of detection design difficulty and the like, and achieve the effect of good promotion significance.
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[0053] Preferably, the specific steps of the preparation method are as follows:
[0054]Add the solution of Compound A and Compound B into HOBT, EDC, DMF and CH 2 Cl 2 In, add piperazine and mix and react at room temperature.
[0055] In some specific embodiments, the compound A, compound B, HOBT, EDC and piperazine are added in a molar ratio of 0.8-1.2:0.8-1.2:1.2-1.7:1.2-1.7:1-1.4.
[0056] In some specific embodiments, the DMF, CH 2 Cl 2 The volume ratio is 0.8-1.2:3.8-4.2.
[0057] In this series of examples, the ratio of compound A to DMF is 0.8-1.2 mmol: 1.8-2.2 mL.
[0058] Further preferably, the preparation method further includes an elution purification step.
[0059] In some specific embodiments, the reacted product is purified by thin layer chromatography.
[0060] In this series of examples, CH 2 Cl 2 / CH 3 OH as eluent.
[0061] Preferably, the compound A is synthesized by dimeric amine and 7-hydroxycoumarin.
[0062] In some specific embodiments, the...
Embodiment 1
[0079] Synthesis and characterization of embodiment 1 fluorescent probe compound
[0080] 7-Hydroxycoumarin: 2,4-dihydroxybenzaldehyde (0.62g, 3.08mmol), diethyl malonate (0.62g, 3.08mmol), 25mL absolute ethanol, 0.5mL piperidine, 2d glacial acetic acid Heated to reflux for 8h. After the reaction is completed, add cold water to precipitate to obtain coumarin ethyl ester. Heat 4g of ethyl coumarin, 3g of NaOH, 20mL of absolute ethanol, and 100mL of water to dissolve for 15min. After cooling down slightly, pour the reaction product into 10mL of concentrated hydrochloric acid and 50mL of water. A pale yellow crystal is precipitated, which is the product.
[0081] Compound A: To a solution of dipolyamine (0.62 g, 3.08 mmol) in 30 mL of acetonitrile was added aqueous formaldehyde (37%) (0.27 mL, 3.08 mmol). After heating at 60° C. for 0.5 h, 7-hydroxycoumarin (0.50 g, 3.08 mmol) in 30 mL of acetonitrile was added. The reaction was continued for 1 hour and the reaction was monito...
Embodiment 2
[0084] Characterization information and application of embodiment 2 fluorescent probe compound
[0085] The compound prepared in Example 1 is verified by its compound structure by NMR and mass spectrometry, wherein the mass spectrum of the fluorescent probe compound described in Example 1 is as follows: figure 1 shown.
[0086] The NMR data are as follows: 1 H NMR (400MHz, DMSO-d 6 )8.52(d, J=4.0Hz, 2H), 8.10(d, J=4.0Hz, 1H), 7.97(s, 1H), 7.95(d, J=1.2Hz, 2H), 7.74(d, J= 1.6Hz,1H),7.71(d,J=4.0Hz,2H),7.69(s,2H),7.52(d,J=0.8Hz,2H), 7.50(t,J=0.8Hz,2H)7.48( d,J=0.8Hz,2H),7.42(s,1H),7.40(d,J=0.8Hz,2H),7.37(t,J=0.8Hz,2H),7.36(d,J=0.8Hz, 1H), 6.88(d, J=3.6Hz, 1H), 5.27(t, J=4.4Hz, 2H), 4.74(d, J=15.2Hz, 1H), 3.95(s, 4H), 3.46(t, J=6.0Hz, 4H), 3.42(s, 2H), 3.40(t, J=5.2Hz, 4H). 13 C NMR (101MHz, DMSO-d 6 )172.51,168.99,162.88,162.73,158.39,157.92,157.75, 157.66,156.36,155.60,155.05,154.33,151.10,150.24,149.45,148.81, 148.77,146.66,144.40,144.28,143.27,137.61,137.26,136.53,135.5...
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