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Spirobifluorene fluorescence probe as well as preparation method and application thereof

A fluorescent probe, spirobifluorene technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effect of wide detection range, high sensitivity and selectivity, and high sensitivity

Inactive Publication Date: 2014-04-23
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the current research on pH fluorescent probes is limited to the effective detection of pH value under single acidic or alkaline conditions (Francisco Galindo, M.Isabel Burguete, Laura Vigara, Santiago V.Luis, Nurul Kabir, Jelena Gavrilovic, and David A. Russell, Angew. Chem. Int. Ed. 2005, 44, 6504-6508)

Method used

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  • Spirobifluorene fluorescence probe as well as preparation method and application thereof
  • Spirobifluorene fluorescence probe as well as preparation method and application thereof
  • Spirobifluorene fluorescence probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] 1), the synthesis of 4,4'-dimethylbiphenyl

[0063] Under nitrogen protection, successively weigh 3g (125mmol) of dry magnesium powder, 0.2g (1.2mmol) of ferric chloride in a 100ml dry three-necked flask, then weigh 11g (64.3mmol) of p-bromotoluene in 50ml and dry in a constant pressure dropping funnel. Inject 60 ml of anhydrous THF into the three-necked flask, and vigorously stir at room temperature. First add 5% p-bromotoluene rapidly and dropwise after the reaction is initiated. After the dropwise addition was completed, the reaction was continued for 30 min, the reaction was stopped, cooled to room temperature, and filtered with suction to obtain a black filtrate, and the solvent was removed to obtain a black paste. Add 50ml of dichloromethane and 30ml of water in sequence, vibrate vigorously, and a lot of flocs appear in the solution. Slowly add dilute hydrochloric acid solution dropwise to the solution and shake continuously until the flocs disappear.

[0064]...

Embodiment 2

[0074] Embodiment 2 Compound (I) to the selectivity of silver ion (1)

[0075] Using the compound (I) synthesized above, the selectivity to silver ions was evaluated by fluorescence method. Compound (I) is dissolved in acetonitrile: water=15:1 (volume ratio) in the mixed solvent, makes its concentration be 1 * 10 -5 M. Then add different metal ions respectively, so that the concentration of metal ions is 1×10 -4 M, to test its fluorescence emission spectrum. Fluorescence test conditions are: excitation wavelength 360nm, slit width 5 / 5, voltage 420V. The results are shown in image 3 middle. From image 3 It can be seen that compound (I) has high selectivity to silver ions (dotted line is silver ion, and the rest are successively Li + 、Na + , Ca 2+ 、Co 2+ 、Cd 2+ 、Cu 2+ , Pb 2+ , Mg 2+ , Mn 2+ , Hg 2+ and blank control). When the compound (I) is combined with silver ions, the fluorescence intensity of the solution is rapidly weakened to almost zero. However, af...

Embodiment 3

[0076] Embodiment 3 compound (I) to the selectivity (2) of silver ion

[0077] Using the compound (I) synthesized above, the selectivity to silver ions was evaluated by the method of absorption spectrum. Compound (I) is dissolved in acetonitrile: water=15:1 (volume ratio) in the mixed solvent, makes compound (I) concentration be 1 * 10 -5 M, and then add different metal ions, so that the concentration of metal ions is 1×10 -4 M, the absorption spectrum of test compound (I). The results are shown in Figure 4 Middle (dashed line is silver ion, the rest are Li + 、Na + , Ca 2+ 、Co 2+ 、Cd 2+ 、Cu 2+ , Pb 2+ , Mg 2+ , Mn 2+ , Hg 2+ and blank control). From Figure 4 It can be seen that compound (I) has high selectivity to silver ions, and when compound (I) is combined with silver ions, the absorbance of the solution is rapidly weakened. However, after compound (I) is mixed with other metal ions, the absorbance hardly changes. The abscissa is the wavelength (nm), and th...

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Abstract

The invention discloses a spirobifluorene fluorescence probe which is 2,7-di(benzimidazole) spirobifluorene. According to the invention, the structural formula of a product is shown in a formula (I). The preparation method of the spirobifluorene fluorescence probe comprises the following steps: carrying out coupling reaction, bromination, Grignard reaction, dehydration cyclization reaction and oxidization reaction on parabromotoluene which is used as a raw material so as to obtain a spirobifluorene dialdehyde compound; and reacting the spirobifluorene dialdehyde compound with o-phenylenediamine to obtain the compound (I). According to the invention, the raw material is cheap and available, the synthesis route is simple, the yield is high, and the preparation method is suitable for large-scale production. Because the three-dimensional rigid structure of spirobifluorene is introduced, the compound (I) has high fluorescence quantum yield and fluorescence intensity; the compound (I) has high sensitivity and good selectivity when being used for silver ion detection, detection limit of naked eye can reach 10<-5>M, and the detection limit of an instrument can reach 10<-6>M; the response time of the compound (I) on the silver ion is less than 2 seconds; and simultaneously, the compound (I) is a pH fluorescence probe having wide response range and has a good application prospect.

Description

technical field [0001] The invention relates to the field of fluorescent probes for heavy metal ion detection and pH detection, in particular to a spirobifluorene fluorescent probe compound that can be used for silver ion detection and pH detection and a preparation method thereof. Background technique [0002] Fluorescent probes refer to molecules that can change the fluorescence signal (intensity or wavelength) when a certain physical or chemical property of a substance or system changes in a specific system. Fluorescent ion probe is a kind of fluorescent probe, which can convert the molecular / ion binding information into an easily detected fluorescent signal, and then obtain the recognition function of ions. As a sensitive detection method with wide application value, fluorescent ion probes have advantages that other analytical methods such as atomic absorption spectroscopy, ion selective electrode analysis and other traditional methods cannot match, that is, changes in f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/18C09K11/06G01N21/64
Inventor 肖海波殷鸿尧
Owner SHANGHAI NORMAL UNIVERSITY
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