7-(3-alkene butoxy)-3H-phenoxazine-3-ketone as well as preparation method and application thereof
A technology of ozone and reaction, applied in chemical instruments and methods, analysis by making materials undergo chemical reactions, fluorescence/phosphorescence, etc., can solve problems such as poor selectivity and short wavelength, and achieve fast reaction speed, high sensitivity, and huge applications foreground effect
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Embodiment 1
[0041] Example 1: Preparation of 7-(3-enebutoxy)-3H-phenoxazin-3-one shown in formula I
[0042] according to figure 1 The chemical reaction scheme shown in the preparation was carried out.
[0043] Dissolve 7-hydroxyphenoxazinone sodium salt (235mg, 1mmol) in DMF (5mL), add 4-bromo-1-butene (269mg, 2mmol), catalyst potassium carbonate (210mg, 1.5mmol) in the reaction solution and react at 20°C for 12 hours. After the reaction is completed, after cooling, the solvent is concentrated under reduced pressure to obtain a crude product, which is purified by column chromatography using petroleum ether (b.p.60-90°C) / ethyl acetate (1:1, v / v) as eluent. Product 140mg.
[0044] The structural characterization data results of the product are as follows:
[0045] 1 H NMR (300MHz, CDCl 3 ):δ=7.70(d,1H,J=9.0Hz),7.42(d,1H,J=9.9Hz),6.92-6.96(m,1H),6.81-6.86(m,2H),6.33(d, 1H,J=2.1Hz),5.84-5.97(m,1H),5.14-5.24(m,2H),4.10-4.15(m,2H),2.57-2.64(m,2H).
[0046] 13 C NMR (CDCl 3 ,75MHz,298...
Embodiment 2
[0049] Embodiment 2: Spectral properties of compound shown in formula I reacting with different concentrations of ozone
[0050] Weigh 2.67 mg of the compound represented by formula I, and prepare 10 ml of dimethyl sulfoxide solution as the mother solution (1 mM) of the solvent.
[0051] Add 100 μL of the above mother solution dropwise to 50 mM phosphate buffer solution, then add ozone solutions of different concentrations, and then use 50 mM phosphate buffer solution to set the volume to 10 mL (the pH of the phosphate buffer solution is 7.4, and the phosphate is Na 2 HPO 4 -NaH 2 PO 4 , the volume ratio of phosphate buffer solution to mother liquor is 100:1). After reacting at 25°C for 30 min, the fluorescence emission spectrum was measured. When measuring the fluorescence emission spectrum, de-excite at 550nm; the slit width for excitation and emission is 10nm; the voltage is 400V.
[0052] figure 2 It is the fluorescence spectrum of the compound shown in formula I r...
Embodiment 3
[0057] Embodiment 3: Compound shown in formula I reacts with other species (selectivity study)
[0058] Various substances were added to the phosphate buffer solution containing 10 μM 7-(3-enebutoxy)-3H-phenoxazin-3-one: hydrogen peroxide (100 μM), hypochlorite (50 μM), superoxide anion ( 100μM), singlet oxygen (100μM), hydroxyl radical (100μM), nitric acid (250μM), sulfuric acid (250μM), lead ion (100nM), palladium ion (100nM), platinum ion (100nM), sodium nitrite (250μM ), sodium sulfite (250 μM), sodium thiosulfate (250 μM) and ozone (30 μM).
[0059] After reacting at 25°C for 30 min, the fluorescence emission spectrum was measured. When measuring the fluorescence emission spectrum, de-excite at 550nm; the slit width for excitation and emission is 10nm; the voltage is 400V.
[0060] Add 100 μL of 7-(3-enbutoxy)-3H-phenoxazin-3-one stock solution (1 mM) to 10 ml of the solution mixed with the above substances, and then add ozone to make the final concentration 30 μM.
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