Small-molecular fluorescent probe for recognizing H2S, preparation method and application thereof
A fluorescent probe, hydrogen sulfide technology, applied in chemical instruments and methods, fluorescence/phosphorescence, analytical materials, etc., can solve problems such as interfering probe real-time detection, affecting probe detection effect, etc., and achieve strong resistance to other molecular interference. , The post-processing process is simple and the selectivity is good.
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Embodiment 1
[0030] Synthesis of compound 3:
[0031]
[0032] Compound 16-hydroxy-2-naphthaldehyde (0.8mmol, 137.6mg) and compound 2 o-aminothiophenol (1.1eq., 110.0mg) were added to the reaction flask under a nitrogen atmosphere, and then the oxidant Na 2 S 2 o 5 (1.2eq., 182.4mg) and DMF were added to the above reactor at one time, heated at 90°C for 5h under a nitrogen atmosphere, spotted the reaction until the raw materials disappeared, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and reduced The crude product was obtained by pressing and spinning to dry the solvent, and was separated with a silica gel column. The silica gel particle size was 200-300 mesh to obtain compound 3 with a yield of 51%.
[0033] Probe compound NS-H 2 Synthesis of S:
[0034]
[0035] Compound 3 (0.2mmol, 55.4mg) was added to a 25mL reaction flask, then DCM (2.0mL) was added, placed at 0°C, triethylamine (1.2eq., 24.3mg) was added to the above solution, Then, 2,4-dinitrobenzen...
Embodiment 2
[0037] Probe compound NS-H 2 Changes of Fluorescence Spectrum of S Hydrogen Sulfide Fluorescent Probe with the Increase of NaHS Adding Equivalent
[0038] Get the probe NS-H that embodiment 1 prepares 2 S was dissolved in N,N-dimethylformamide (DMF) to make a 1 mmol / L stock solution. Take 30μL from the stock solution and add it to a 5mL centrifuge tube, add different equivalents (0-80eq) of NaHS standard solution, use PBS buffer solution (0.1mol / L, pH=7.5) and DMF with a volume ratio of 1:1 The solution was diluted to 3 mL and its fluorescence properties were measured. Fluorescence spectra such as figure 2 shown. Depend on figure 2 It can be seen that the fluorescence gradually increases with the increase of NaHS addition equivalent.
Embodiment 3
[0040] Probe NS-H 2 Changes in S versus time-dependent fluorescence spectra
[0041] Take 30 μL from the fluorescent probe stock solution in Example 2 and add it to a 5mL centrifuge tube, add NaHS (20eq.) standard solution, and use EtOH / H 2 O (1:1, v / v) was diluted to 3 mL (10 μM), and its fluorescence properties were measured. Fluorescence spectra such as image 3 shown. Depend on image 3 Visible, adding probe NS-H 2 After S, adding NaHS directly, the fluorescence intensity can reach the maximum quickly within 0.5min, realizing the H 2 Rapid detection of S.
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