Preparation method and application of 9,9'-(4,4'-biphenyl)bisfluorone bromination reagent

A technology of bifluorone and biphenyl, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, can solve the problems of unsatisfactory sensitivity and selectivity, and achieve improved sensitivity, fast response, and simple preparation methods Effect

Inactive Publication Date: 2015-09-16
SHANXI DATONG UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0004] The present invention provides a 9,9'-(4,4'-biphenyl)bisfluo

Method used

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  • Preparation method and application of 9,9'-(4,4'-biphenyl)bisfluorone bromination reagent
  • Preparation method and application of 9,9'-(4,4'-biphenyl)bisfluorone bromination reagent
  • Preparation method and application of 9,9'-(4,4'-biphenyl)bisfluorone bromination reagent

Examples

Experimental program
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Example Embodiment

[0029] Example

[0030] Such as figure 2 As shown, a 9,9'-(4,4'-biphenyl) bisfluorone bromide reagent, referred to as 9,9'-QBBPBF for short, has the molecular structure

[0031] .

[0032] Such as image 3 As shown, the preparation method of 9,9'-QBBPBF includes the following steps:

[0033] (1) Synthesis of p-benzoquinone: Dissolve 60 g of hydroquinone in 1000 mL of water at 50°C, cool to a temperature of 20°C, and slowly drop 32 mL of concentrated H 2 SO 4 , Stir vigorously, control the reaction temperature ≤30℃, add 400mL K with a concentration of 0.2g / ml at a rate of 0.5~1.0mL / min 2 Cr 2 O 4 The solution was cooled to room temperature after the addition was completed, filtered with suction, and the precipitate was washed with deionized water until the filtrate was light yellow, and the precipitate was dried at 80°C to obtain 32.3 g of yellow p-benzoquinone with a yield of 54%;

[0034] (2) Synthesis of trimellitol triacetate: In a 100mL beaker, add 28.0mL acetic anhydride and 1.0m...

Example Embodiment

[0037] Experimental example 1: Photometric analysis and detection of Mo(VI) in alkaline medium.

[0038] In a 25mL volumetric flask, sequentially add 5μg of Mo(VI) standard solution, 2.0% Triton X-100 aqueous solution 2.0mL, 0.3g / L 9,9'-QBBPBF ethanol solution 3.0mL, pH8.0 borax- 1.5 mL of sodium hydroxide buffer solution, dilute to the mark with water, shake well, take the blank reagent as a reference, use a 1cm cuvette to measure the absorbance of the complex at 670nm, the apparent molar absorption coefficient is 1.9×10 5 L·mol -1 ·Cm -1 . The results of comparison between the sensitivity of the photometric analysis method for measuring Mo(VI) and the sensitivity of the existing similar reagents for measuring molybdenum are shown in Table 1. The results show that the photometric method for molybdenum ion determination of the present invention has high sensitivity.

[0039] Table 1: The sensitivity of several reagents to determine molybdenum

[0040]

[0041] The results of compari...

Example Embodiment

[0047] Experimental example 2: Fluorescence detection of Mn(Ⅱ) by 9,9'-QBBPBF.

[0048] Sample processing: According to the method in the literature [Du Rongshan, Huang Liping, Journal of Analytical Science, 2010, 26(5), 535-538], take two different urine samples of 100 mL each and place them in an Erlenmeyer flask. Add 25.0mL concentrated nitric acid, 4.0mL perchloric acid, heat to digest until colorless, and concentrate to 1.0-2.0mL. Remove and cool, add a small amount of water, transfer to a 10mL centrifuge tube, and wash the Erlenmeyer flask twice with a small amount of double-distilled water, and pour the washing liquid into the centrifuge tube. Centrifuge at 8000r / min for 10min, then transfer all the supernatant into a beaker, use 0.2mol / L NH 3 ·H 2 O neutralize to PH=7.0, finally dilute to a 100mL volumetric flask, shake well. Take 5.00mL test solution, add 1.00mL167μg / mL ascorbic acid solution, and remove Fe in the sample 3+ Reduced to Fe 2+ , 1.00mL500μg / mL thiourea sol...

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Abstract

The invention belongs to the technical field of phenylfluorone compounds, and provides a 9,9'-(4,4'-biphenyl)bisfluorone bromination reagent, and a preparation method and an application thereof in order to solve the problem of unsatisfactory sensitivity and selectivity of reagents for detection of heavy metal ions in the prior art. 4,4'-Biphenyldicarboxaldehyde with a large conjugated system reacts with 1,2,4-trihydroxybenzene triacetate to synthesize the novel bisfluorone reagent with a larger conjugated system, so the sensitivity and the fluorescence characteristic of the reagent are enhanced. The 9,9'-(4,4'-biphenyl)bisfluorone bromination reagent can be used in detection of Mo (VI) ions under alkaline conditions and fluorescence detection of Mn (II). The reagent is a highly-selective and highly-selective fluorescence analysis reagent for detecting Mo (VI) and Mn (II), and is a luminosity analysis developer with a good analysis performance.

Description

technical field [0001] The invention belongs to the technical field of phenylfluorone compounds, and in particular relates to a preparation method and application of a 9,9'-(4,4'-biphenyl)bisfluorone bromide derivative. Background technique [0002] The fluorone reagent refers to a class of triphenylmethane derivatives containing a 2,3,7-trihydroxy-6-keto-pyran ring structure in the molecule. The compound formed when the 9-position hydrogen atom is replaced by phenyl, also known as phenylfluorone (structure such as figure 1 ). Phenylfluorone is mostly orange or red crystals, hardly soluble in water and cold ethanol, but easily soluble in acidified ethanol. The compound has strong fluorescence due to its large conjugated system. Since there are 3 hydroxyl groups at the 2, 3 and 7 positions, and the oxygen atom in the hydroxyl group has 2 lone pairs of electrons, it is easy to form a coordination bond with the empty orbital of the metal ion, so it can form a complex with a ...

Claims

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Application Information

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IPC IPC(8): C07D311/82C09K11/06G01N21/64
CPCC07D311/82C09K11/06C09K2211/1088G01N21/6428
Inventor 解海樊月琴
Owner SHANXI DATONG UNIV
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