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Carbazole-benzimidazole group-containing ratiometric fluorescent probe compound for detection and identification of Cr<3+> and preparation method thereof

A ratiometric fluorescent probe, benzimidazole-based technology, applied in the research field of synthesis and its ion recognition performance, can solve the problems of fluorescence quenching, limited measurement sensitivity, probe concentration and sample being easily disturbed by the environment, and achieve high Selectivity, simple and convenient post-processing, and the effect of ratiometric fluorescence analysis

Inactive Publication Date: 2015-04-08
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a variety of fluorescent probes that can be used for the detection of metal ions have been reported, but for Cr 3+ There are relatively few probes, and the reported Cr 3+ Most of the probes are fluorescence quenching, this is because the Cr 3+ The paramagnetism of the probe will cause fluorescence quenching; due to the simple change of the fluorescence intensity, the concentration of the probe and the sample are easily disturbed by the environment, which limits the improvement of the measurement sensitivity.

Method used

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  • Carbazole-benzimidazole group-containing ratiometric fluorescent probe compound for detection and identification of Cr&lt;3+&gt; and preparation method thereof
  • Carbazole-benzimidazole group-containing ratiometric fluorescent probe compound for detection and identification of Cr&lt;3+&gt; and preparation method thereof
  • Carbazole-benzimidazole group-containing ratiometric fluorescent probe compound for detection and identification of Cr&lt;3+&gt; and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of target compound L

[0027] Dissolve 2.80g (5mmol) of 3-formyl-N-n-hexylcarbazole in a small amount of ethanol, slowly add 0.54g (5mmol) of ethanol solution of o-phenylenediamine, drop in catalytic amount of glacial acetic acid, heat up to 80°C and reflux After reacting for 2 hours, the heating was stopped and cooled to room temperature. A light yellow solid precipitated out. It was filtered by suction and recrystallized with ethanol to obtain 1.23 g of a beige solid with a yield of 78.25%. 1 H-NMR (DMSO-d 6 ,400Hz): δ(ppm):8.61(s,1H),8.07(d,J=8.0Hz,1H),7.91(s,3H),7.74(d,J=8.0Hz,2H),7.63(t ,2H),7.55(d,J=8.0Hz,1H),7.51-7.46(m,2H),7.42(t,J=7.8Hz,1H),7.25(m,2H),7.15-7.09(m, 3H), 5.82(d, 2H), 4.42(t, 2H), 4.31(t, 2H), 1.77(m, 2H), 1.69(m, 2H), 1.19(m, 12H), 0.76(m, 6H ).FT-IR(KBr,cm -1 ):3442(=C-H),2856-2953(-CH 2 ,-CH 3 ), 1629, 1600 (Ar-H), 1455 (-CH 3 ), 1424 (-C=C-), 1331 and 1238 (-C=N-), 746 and 733 (Ar-H); HRMS (ESI): m / z calcd fo...

Embodiment 2

[0028] Embodiment 2: the ultraviolet-visible absorption spectrometry of compound L

[0029] Accurately weigh 6.33 mg of compound L, dissolve and prepare it 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. Their UV-Vis spectra and fluorescence spectra were measured respectively.

[0030] Take 3mL concentration as 1.0×10 -5 mol / L of the sample to be tested is placed in a quartz cuvette (the thickness of the quartz cuvette is 1cm), and then 30 μL of the concentration of 1.0×10 -3 mol / L of various metal ions (Na + , K + , Ag + , Ca2+ , Mg 2+ , Mn 2+ , Zn 2+ , Cd 2+ , Cr 3+ , Cu 2+ , Ni 2+ ,Co 2+ , Fe 3+ , Fe 2+ , Hg 2+ ) solution, shake well, and measure the UV-Vis absorption spectrum of the solution after 1min (as attached figure 1 shown). Before adding metal ions, the UV-Vis absorption spectrum of L showed two clear absorption ...

Embodiment 3

[0031] Embodiment 3: the determination of the ultraviolet-visible absorption spectrometry titration experiment and detection limit of compound L

[0032] Take 3mL concentration as 1.0×10 -5 mol / L compound L acetonitrile solution in quartz cuvette, add 3 μL each time the concentration is 1.0×10 -3 mol / L Cr 3+ Ionic acetonitrile solution, shake well, and measure the UV-Vis absorption spectrum of the solution after equilibration (as attached figure 2 shown, the illustration shows the addition of Cr 3+ Absorbance change of L at 336nm). With Cr 3+ With the gradual addition of ions, the absorption peaks of compound L at 267nm and 297nm weakened, while the absorbance at 336nm gradually increased, and an obvious isoabsorbance point appeared at 306nm, indicating that compound L and Cu 2+ A stable complex was formed. at c(Cr 3+ ): c(L) > 0.9, the absorbance does not change anymore, at 1.0×10 -6 ~1.3×10 -5 In the range of mol / L, Cr 3+ There is a good linear relationship betwee...

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Abstract

The invention discloses a carbazole-benzimidazole group-containing ratiometric fluorescent probe compound for detection and identification of Cr<3+> and a preparation method thereof. The carbazole-benzimidazole group-containing ratiometric fluorescent probe compound has a general structural formula (L), and in the general structural formula (L), R represents C2-8 alkyl. The synthesized carbazole-benzimidazole group-containing derivative has multiple functions. Through a UV-visible spectrophotometry and a fluorescent spectrometry, Cr<3+> identification and quantitative determination are realized. Because of obvious color change, the carbazole-benzimidazole group-containing ratiometric fluorescent probe compound can be used as a colorimetric probe for identification of Cr<3+> and can also be used as a Cr<3+> ratiometric fluorescent probe. In the presence of other ions, the carbazole-benzimidazole group-containing ratiometric fluorescent probe compound has good interference resistance, high selectivity and good sensitivity.

Description

technical field [0001] The invention relates to the field of metal ion detection and fluorescent molecular probes, in particular to a 3+ Synthesis of ratiometric fluorescent probe molecules containing imidazole groups for detection and recognition of carbazole derivatives and their ion recognition properties. 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 the research objects in many disciplines such as chemistry, life science, environmental science and medicine. The identification and detection of metal ions in solution is a hot issue in analytical chemistry. Fluorescent molecular probe technology has been widely used in the detection of various metal ions due to its advantages of good selectivity, high sensitivity, simplicity and sp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D403/14G01N21/64G01N21/31
Inventor 李村朱维菊方敏张晴
Owner ANHUI UNIVERSITY