Carbazole-thiophene schiff base fluorescent probe compound for detecting and recognizing Fe<3+> and Cr<3+>

A technology of thienyl Schiff bases and fluorescent probes, applied in organic chemistry, fluorescence/phosphorescence, luminescent materials, etc., can solve problems such as high cost, poor reagent selectivity, and complex equipment, and achieve naked-eye recognition and colorimetry The effect of the analysis

Inactive Publication Date: 2014-03-26
ANHUI UNIVERSITY
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Problems solved by technology

[0005] All along, for Fe 3+ 、Cr 3+ The identification and determination methods of ions mainly include spectrophotometry, electrochemical analysis, high performance liquid phase analysis, atomic absorption method, etc., but in the above methods, some reagents have poor selectivity, and when used for the analysis of some complex samples, Appropriate pretreatment is often required, and some instruments and equipment are complex and costly, which are not ideal for identifying and detecting Fe in organisms. 3+ 、Cr 3+ As a simple, effective and economical method, the fluorescence analysis method has high sensitivity and can minimize the damage of the measured cells through fluorescence imaging. It is currently becoming one of the most widely used methods in the biological world.

Method used

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  • Carbazole-thiophene schiff base fluorescent probe compound for detecting and recognizing Fe&lt;3+&gt; and Cr&lt;3+&gt;
  • Carbazole-thiophene schiff base fluorescent probe compound for detecting and recognizing Fe&lt;3+&gt; and Cr&lt;3+&gt;
  • Carbazole-thiophene schiff base fluorescent probe compound for detecting and recognizing Fe&lt;3+&gt; and Cr&lt;3+&gt;

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: Synthesis of Schiff base compound (L)

[0021] In a 100mL round bottom flask, add 2.5g (10mmol) 3-formyl-9H-hexylcarbazole, 1.78g (10mmol) NBS, 0.05gBPO, dissolve with 20mL DMF, reflux at room temperature for 48h in the dark, wash with a large amount of water, Milky white and dark yellow oily liquid, extracted with dichloromethane, combined organic phases and washed with anhydrous MgSO 4 Dry, suction filter the next day, spin dry the organic phase, dissolve the product with a small amount of dichloromethane, add a small amount of silica gel, and separate through a silica gel column (petroleum ether: ethyl acetate = 10:1) to obtain 3-bromo-9H-hexyl Carbazole (1), the product is 2.53g yellow liquid, the yield is about 76.67%.

[0022] Weigh 0.94 g (6 mmol) of 2-formyl 5-boronic acid thiophene and 0.04 g tetrakistriphenylphosphine palladium in a three-necked flask, vacuumize, and fill with N 2 For protection, take 2.0mL 3-bromo-9H-hexylcarbazole (1), 40mL D...

Embodiment 2

[0024] Embodiment 2: the ultraviolet-visible absorption spectrometry of compound L

[0025] Accurately weigh 2.5 mg of compound L, dissolve and prepare to a concentration of 0.5×10 -3 mol / L acetonitrile stock solution, accurately pipette the stock solution and dilute to a concentration of 1.0×10 -5 mol / L of the solution to be tested. Take 3mL concentration as 1.0×10 -5 mol / L of the sample to be tested in a quartz cuvette (the thickness of the quartz cuvette is 1cm), and then add 30μL of the concentration of 1.0×10- 3 mol / L of various metal ions (Na + , K + , Ag + , Ca 2+ , Mg 2+ , Mn 2+ , Cd 2+ , Cr 3+ , Cu 2+ , Ni 2+ ,Co 2+ , Fe 3+ , Fe2+ , Hg 2+ ) solution, shake well, and measure the UV-Vis absorption spectrum of the solution after 30 seconds (as shown in the accompanying drawing figure 1 shown). Before adding metal ions, the UV-Vis absorption spectrum of L showed two clear absorption peaks at 293nm and 410nm, when adding Fe 3+ After ions, the absorption p...

Embodiment 3

[0026] Embodiment 3: the determination of the ultraviolet-visible absorption spectrometry titration experiment and detection limit of compound L

[0027] Take 3mL concentration as 1.0×10 -5 The acetonitrile solution of mol / L compound L was placed in a quartz cuvette, each time adding 3 μL, the concentration was 1.0×10 -3 mol / LFe 3+ Ionic acetonitrile solution, shake well, and measure the UV-visible absorption spectrum of the solution after equilibration (as shown in the accompanying drawing figure 2 shown). With Fe 3+ With the addition of ions, the absorbance of compound L at 293nm gradually increased, and the absorption peak gradually blue-shifted, while the absorbance at 410nm gradually weakened and gradually blue-shifted, until the absorption peak at 410nm blue-shifted to 376nm. Compound L can react with Fe in acetonitrile solution 3+ The ions form a stable complex, and a new absorption peak appears at 314nm, Fe 3+ ions at 1.0 x 10 -6 ~1.3×10 -5 In the range of mol...

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Abstract

The invention relates to a carbazole-thiophene schiff base fluorescent probe compound for detecting and recognizing Fe<3+> and Cr<3+>. The structural generative formula of the compound is shown in (I), wherein R refers to alkyl containing 2 to 10 carbon atoms. The Schiff base derivative synthesized through the compound has multiple functions and can be used for recognizing and quantitatively detecting the Fe<3+> and Cr<3+> through a visible spectrophotometry and a fluorescent spectrometry, the carbozole-thiophene Schiff base fluorescent probe compound can be used as a colorimetric probe for recognizing the Fe<3+> ions through eyes through the obvious color variation and also can be used as a Fe<3+> and Cr<3+> ion fluorescent probe; moreover, the interference resistance is good and the selectivity and sensitivity are high in the presence of other ions.

Description

technical field [0001] The invention relates to the fields of metal ion detection and fluorescent molecular probes, specifically a method for Fe 3+ 、Cr 3+ Synthesis of Molecular Derivatives Containing Thienylcarbazole-Schiff Base Fluorescent Probes for Detection and Identification and Their Application in Ion Recognition. Background technique [0002] In recent years, with the rapid development of chemical sensors, the study of fluorescent probes has attracted more and more attention in many fields such as chemistry, biology, medicine, and environment, and has become a major research hotspot. Metal ions are research objects in many disciplines such as chemistry, environmental science, life science and medicine, so the identification and detection of metal ions in solution has become a hot issue in analytical chemistry research. Fluorescent molecular / ion probe technology has been widely used in the detection of various metal ions because of its advantages of good selectivit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D409/04G01N21/64G01N21/33
Inventor 李村朱维菊方敏杨莲莲
Owner ANHUI UNIVERSITY
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