Tetraphenyl ethylene Schiff base Zn2+ fluorescent probe and preparation method and application thereof
A tetraphenylethylene, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as limited applications, and achieve the effects of low detection limit, high anti-interference ability, and high detection sensitivity
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[0040] The preparation of tetraphenylethylene fluorescent probes of the present invention can be represented by the following reaction formula:
[0041]
[0042] Specifically, the present invention first dissolves 4-hydroxytetraphenylethylene and hexamethylenetetramine in a mixed solvent of acetic acid and trifluoroacetic acid, and reacts to obtain the first intermediate product 4-hydroxyl-5-formyl tetraphenylethylene In the present invention, the molar ratio of 4-hydroxytetraphenylethylene to hexamethylenetetramine is preferably 1:(1.0~1.5), more preferably 1:1.0, and the reaction temperature is preferably 70~100°C, more preferably 90 °C, the reaction time is preferably 2 to 5 hours, more preferably 3 hours.
[0043] Then 2-aminobenzothiazole is dissolved in ethylene glycol solvent, and concentrated sulfuric acid is added, then slowly drips hydrazine hydrate, reacts, obtains the second intermediate product 2-hydrazinobenzothiazole, 2-aminobenzothiazole in the present inven...
Embodiment 1
[0059] Tetraphenylethylene Schiff base Zn 2+ Preparation of fluorescent probe L:
[0060] Synthesis of the first intermediate product: put 1g (2.87mmol) of 4-hydroxytetraphenylethylene and 0.40g (2.87mmol) of hexamethylenetetramine into a 100mL round bottom flask, add 8mL acetic acid and 8mL trifluoro Dissolve acetic acid, heat to 90°C, stir for 3 hours and then stop the reaction; cool down to 20°C, remove solvent acetic acid and trifluoroacetic acid by rotating the liquid under reduced pressure, stir in 4.0g of silica gel, use petroleum ether: ethyl acetate = 50:1 The eluent was separated by column chromatography to obtain a yellow solid (4-hydroxy-5-formyl tetraphenylethylene), and the yield was 48.6%.
[0061] Synthesis of the second intermediate product: 3.5g (23.30mmol) of 2-aminobenzothiazole was put into a 50mL round-bottomed flask, dissolved in 25ml of ethylene glycol, added 0.5mL of concentrated sulfuric acid under magnetic stirring, and heated To 70°C, add 9.3g (18...
Embodiment 2
[0065] Tetraphenylethylene Schiff base Zn 2+ Fluorescent Probe L on Zn 2+ Selective detection of:
[0066] Configure a tetraphenylethylene fluorescent probe dimethyl sulfoxide standard solution with a molar concentration of 1mmol / L; and add a metal ion solution with a molar concentration of 10mmol / L therein; after stirring evenly, detect the change in the fluorescence emission spectrum of the solution within 15s; Among them, metal ions include: Zn 2+ , Pb 2+ , Ni + , Na + , Mn 2+ , Mg 2+ , Li + , K + , Hg 2+ , Fe 3+ , Fe 2+ , Cu 2+ , Cr 3+ ,Co 2+ , Cd 2+ , Ca 2+ , Ba 2+ , Al 3+ , Ag + ;
[0067] Such as Figure 4 As shown, the fluorescent probe has almost no emission peak at 479nm, when adding Zn 2+ Finally, the fluorescent probe solution has a strong emission peak at 479nm, so the experimental results show that only adding Zn 2+ , can cause the fluorescent probe solution to show obvious fluorescence enhancement at 479nm, the tetraphenylethylene Schiff b...
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