Spirobifluorene fluorescence probe as well as preparation method and application thereof

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

Inactive Publication Date: 2012-08-15
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) Synthesis of 4,4’-Dimethylbiphenyl

[0063] Under the protection of nitrogen, weigh 3g (125mmol) of dry magnesium powder, 0.2g (1.2mmol) of ferric chloride in a 100ml dry three-necked flask, and then weigh 11g (64.3mmol) of p-bromotoluene in 50ml and dry The constant pressure dropping funnel. 60 ml of anhydrous THF was poured into a three-necked flask, and stirred vigorously at room temperature. First, 5% p-bromotoluene was quickly added dropwise, and after the reaction started, slowly dropwise addition. After the addition is complete, continue the reaction for 30 minutes, stop the reaction, cool to room temperature, and filter with suction to obtain a black filtrate, and remove the solvent to obtain a black paste. Add 50ml of dichloromethane and 30ml of water successively, shake vigorously, and a lot of floccules appear in the solution. Slowly add dilute hydrochloric acid solution dropwise to the solution and shake continuously until the flocs disappear.

[0064] Sep...

Embodiment 2

[0074] Example 2 The selectivity of compound (I) to silver ions (1)

[0075] The compound (I) synthesized above was used to evaluate the selectivity to silver ions by a fluorescence method. The compound (I) was dissolved in a mixed solvent of acetonitrile: water = 15:1 (volume ratio) to make the concentration 1×10 -5 M. Then add different metal ions to make the concentration of metal ions 1×10 -4 M, 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 in. From image 3 It can be seen that compound (I) has high selectivity to silver ions (the dotted line is silver ions, and the rest are Li + , Na + , Ca 2+ , Co 2+ , Cd 2+ , Cu 2+ , Pb 2+ , Mg 2+ , Mn 2+ , Hg 2+ And blank control). When compound (I) is combined with silver ions, the fluorescence intensity of the solution rapidly weakens to almost zero. After compound (I) is mixed with other metal ions, there is alm...

Embodiment 3

[0076] Example 3 The selectivity of compound (I) to silver ions (2)

[0077] The compound (I) synthesized above was used to evaluate the selectivity to silver ions by the method of absorption spectroscopy. The compound (I) was dissolved in a mixed solvent of acetonitrile: water = 15:1 (volume ratio), so that the concentration of the compound (I) was 1×10 -5 M, and then add different metal ions to make the metal ion concentration 1×10 -4 M, the absorption spectrum of test compound (I). The results are shown in Figure 4 Medium (the dotted 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 a high selectivity to silver ions, and when compound (I) is combined with silver ions, the absorbance of the solution decreases rapidly. After compound (I) is mixed with other metal ions, there is almost no change in absorbance. The abscissa is the wavelength (nm), a...

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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 probe refers to a molecule whose fluorescence signal (intensity or wavelength) can change correspondingly 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 molecule / ion binding information into fluorescent signal that can be easily detected, and then obtain ion recognition function. As a sensitive detection method with a wide range of applications, the fluorescent ion probe has the advantages that other analytical methods such as atomic absorption spectroscopy, ion selective electrode analysis and other traditional methods cannot match, that...

Claims

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Application Information

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