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Chloride ion fluorescent probe and preparation method and application thereof

A technology of fluorescent probes and chloride ions, which is applied in the field of ion detection in chemical analysis, can solve problems such as limiting anion types and fluorescence response sensitivity, and achieve the effects of convenient identification, good ion selectivity, and simple operation

Active Publication Date: 2013-10-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The working mechanism of traditional anionic fluorescent probes is mostly to use the anion to form a strong hydrogen bond with the probe molecule, and complete the detection through the photoinduced charge transfer process or change the conformation of the fluorophore. This method has certain limitations. The anion species detected and the sensitivity of the fluorescence response

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  • Chloride ion fluorescent probe and preparation method and application thereof
  • Chloride ion fluorescent probe and preparation method and application thereof
  • Chloride ion fluorescent probe and preparation method and application thereof

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preparation example Construction

[0036] Preparation formula of the present invention:

[0037]

Embodiment 1

[0039]Under nitrogen protection, 100mg (0.24mmol) 2,7-dibromo-9-cycloheptatrienylfluorene, 106mg (0.53mmol) 2-biphenylboronic acid, 0.47g (3.4mmol) potassium carbonate, then add the mixed solvent of toluene (8ml), ethanol (8ml), water (8ml) in the ratio of 1:1:1 with the volume ratio, and add the tetrakis (triphenylene) of catalytic amount Phosphine) palladium, heated to reflux, reacted for 6 hours, cooled, extracted the reaction solution with dichloromethane, combined the organic layers, washed with saturated brine, dried the organic phase over magnesium sulfate, filtered, evaporated the solvent, and separated by column chromatography to obtain 2 , 7-bis(biphenyl-2-yl)-9-cycloheptatrienylene fluorene 42 mg, yield 31%.

Embodiment 2

[0041] Under nitrogen protection, 100mg (0.24mmol) 2,7-dibromo-9-cycloheptatrienylfluorene, 144mg (0.73mmol) 2-biphenylboronic acid, 0.47g (3.4mmol) potassium carbonate, then add the mixed solvent of toluene (8ml), ethanol (8ml), water (8ml) in the ratio of 1:1:1 with the volume ratio, and add the tetrakis (triphenylene) of catalytic amount Phosphine) palladium, heated to reflux, reacted for 12 hours, cooled, extracted the reaction solution with dichloromethane, combined the organic layers, washed with saturated brine, dried the organic phase with magnesium sulfate, filtered, evaporated the solvent, and separated by column chromatography to obtain 2 , 55 mg of 7-bis(biphenyl-2-yl)-9-cycloheptatrienylene fluorene, yield 41%.

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Abstract

The invention discloses a chloride ion fluorescent probe and a preparation method and application thereof. The probe comprises 2,7-bis(biphenyl-2-yl)-9-cycloheptatrienylidene and 2,7-bis(biphenyl-4-yl)-9-cycloheptatrienylidene, and is prepared by the following steps of: adding 1 equivalent unit of 2,7-dibromo-9-cycloheptatrienylidene, 2.2 to 3.0 equivalent units of aryl boric acid and 14 equivalent units of potassium carbonate under the protection of nitrogen gas; adding a mixed solvent of methyl benzene, ethanol and water in a volume ratio of 1:1:1 to 2:2:1 into the mixture; adding a catalytic amount of tetra(triphenylphosphine)palladium into the mixture; heating and refluxing the mixture; reacting the mixture for 6 to 12 hours; cooling reaction liquid; extracting the reaction liquid with methylene dichloride; combining organic layers; washing the combined organic layer with saturated saline solution; drying an organic phase through magnesium sulfate; filtering the organic phase; evaporating the solvent; and performing separation by column chromatography to obtain chloride ion fluorescent probe molecules. The probe has the advantages of high ion selectivity, low detection lower limit, high flexibility, simple operation, broad application prospect, high practical value and capability of effectively distinguishing chloride ions from other oxyacid anions and the like.

Description

technical field [0001] The invention relates to the field of chemical analysis ion detection, in particular to a chloride ion fluorescent probe and its preparation method and application. Background technique [0002] Chloride ion is a common and important anion. Chloride widely exists in the human body, and plays an important role in regulating the water balance mechanism in organisms and the osmotic pressure inside and outside cells. Therefore, the chloride ion in the environment, especially the chloride ion content in drinking water, will have a decisive impact on human health. Therefore, it is very meaningful to complete the detection of chloride ion accurately and quickly, especially to track its behavior in chemical and biochemical reactions. [0003] Fluorescent probe technology has become a commonly used chemical analysis method because of its advantages of high sensitivity and low detection limit. For the detection of chloride ions, the conventional methods are c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07C13/567C07C1/32G01N21/64
Inventor 吕萍韩清川蒋志韬胡彬彬冯金武
Owner ZHEJIANG UNIV
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