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Organosilicon polymer fluorescent probe for detecting thiocyanate ion, and synthesis and application thereof

A fluorescent probe and thiocyanate technology, applied in the direction of fluorescence/phosphorescence, luminescent materials, material excitation analysis, etc., can solve the problems that affect the application of the probe, the effect has a large impact, and the probe has high biological toxicity

Inactive Publication Date: 2019-05-03
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many of these probes have poor water solubility, low sensitivity, and the change of pH has a great impact on the detection effect. Some probes have high biological toxicity and poor cell membrane permeability. These defects greatly affect the application of the probes.

Method used

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  • Organosilicon polymer fluorescent probe for detecting thiocyanate ion, and synthesis and application thereof
  • Organosilicon polymer fluorescent probe for detecting thiocyanate ion, and synthesis and application thereof
  • Organosilicon polymer fluorescent probe for detecting thiocyanate ion, and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 Synthesis of Compound Probe V1

[0042] (1) Synthesis of Compound A

[0043]

[0044] Dissolve 2.3 g of bisphenol fluorene in 20 mL of ethanol, and then dissolve 0.75 g of paraformaldehyde in 20 mL of toluene. In a 250 mL eggplant flask, add MM NH2 2 g, dissolved in 100 mL of ethanol, then added the prepared formaldehyde solution and bisphenol fluorene solution, heated at 110°C and stirred for reflux for 24 h. Rotary evaporation, drying to obtain compound A.

[0045] (2) Synthesis of Compound B

[0046]

[0047] Dissolve 2.77 g of 4-bromo-1,8-naphthalene anhydride in 50 mL of ethanol, then dissolve 3 g of sodium methyl mercaptide in 50 mL of ethanol, and add them together into a 250 mL eggplant-shaped reaction flask, and stir at room temperature for 24 h. After the reaction, 100 mL of water was added to the reaction flask to obtain a yellow precipitate, which was filtered and dried to obtain a yellow solid, which was purified by column chromatograp...

Embodiment 2

[0051] Example 2 The selectivity of compound V1 fluorescent probe to different anions

[0052] Prepare 5 mL of PBS aqueous solution (pH = 7.4) and the fluorescent probe V1 mother solution obtained in Example 1 at a concentration of 1 mM as a spare.

[0053]Add 10 μL probe stock solution, 225 μL DMSO and 10 equivalents of sodium chloride, sodium acetate, sodium sulfide, sodium bicarbonate, sodium thiocyanate, sodium hypochlorite, sodium nitrite, sodium nitrate, sodium phosphate, sodium sulfate, carbonic acid Sodium solution, dilute to 3 mL with phosphate buffer solution PBS, shake well, after 30 min, perform fluorescence detection (λ ex =405 nm, λ em =530 nm), to establish a histogram of fluorescence intensity after adding each ion solution, such as figure 2 shown. Depend on figure 2 It can be found that other ions have little effect on the fluorescence of compound V1, while the addition of thiocyanate significantly weakens the fluorescence of compound V1.

Embodiment 3

[0054] Example 3 Fluorescence titration detection of different concentrations of thiocyanate on probe V1

[0055] Prepare 10 mL of an aqueous solution with a concentration of 10 mM thiocyanate and a mother solution of the fluorescent probe V1 obtained in Example 1 with a concentration of 1 mM as spares.

[0056] Prepare the probe at a concentration of 10 μM, interact with different concentrations of thiocyanate (5, 10, 15, 20, 25, 30, 35, 40, 50, 60, 70, 80, 90, 100 μM), and conduct Fluorescence detection (λ ex = 405 nm, λ em = 530 nm), calculate the fluorescence intensity in each system, and establish the standard curve of fluorescence intensity and thiocyanate concentration. like image 3 As shown, as the concentration of thiocyanate increases, the fluorescence intensity of the reaction system decreases gradually, and when the concentration of thiocyanate reaches 100 μM, the fluorescence intensity of the reaction system reaches the lowest state.

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Abstract

The invention provides an organosilicon polymer fluorescent probe for detecting a thiocyanate ion, wherein the structural formula is represented as the specification. The fluorescent probe is synthesized from raw materials including: bisphenol fluorene, MMNH2, formaldehyde, 4-bromo-1,8-naphthyl anhydride, sodium methyl mercaptide, etc. The method employs accessible raw materials, is simple in synthetic steps and high in yield. The fluorescent probe can emit fluorescence of thiomethyl naphthalimide; when the thiocyanate ion is added, the probe can specifically recognize the thiocyanate ion, wherein the thiomethyl group in the probe is oxidized into a dithio bond, and the fluorescence is dimmed. The detection conditions are that excitation wavelength is 405 nm and detection wavelength is 530nm.

Description

technical field [0001] The invention belongs to the field of organic polymer fluorescent probes, in particular to a fluorescent probe for detecting thiocyanate in cells and a synthesis method thereof. Background technique [0002] Silicon, as the second largest type of element contained in the earth's crust, has received extensive attention in recent years. Due to the special physical and chemical properties of Si and Si-O, they have good insulation, aging resistance, biocompatibility and other advantages, and are widely used in biomedical, transportation, electric power, construction, textile and other industries. Silicone polymers have many superior properties. Common silicone polymer materials mainly include silicone oil, silicone rubber, and silicone resin. They have high and low temperature resistance, electrical insulation, moisture resistance, aging resistance, and good physiological inertia, which are incomparable to other polymer materials based on carbon materials...

Claims

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Application Information

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IPC IPC(8): C08G14/12C08G14/06C09K11/06G01N21/64
Inventor 林伟英左育静杨婷新
Owner UNIV OF JINAN
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