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N-benzoyl rhodamine B hydrazine, preparation and use thereof

A technology for the reaction of benzoyl and benzoyl chloride, which is applied in the fields of fluorescence/phosphorescence, organic chemistry, color/spectral characteristics measurement, etc., can solve the problems of application limitation, poor selectivity, and susceptibility to interference, so as to improve detection sensitivity and selectivity High sensitivity, high detection sensitivity, widening application range

Inactive Publication Date: 2008-11-12
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of these methods are mainly poor selectivity, easy to be disturbed, and their application has been greatly restricted.

Method used

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  • N-benzoyl rhodamine B hydrazine, preparation and use thereof
  • N-benzoyl rhodamine B hydrazine, preparation and use thereof
  • N-benzoyl rhodamine B hydrazine, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1. The preparation reaction process of the analytical reagent N-benzoylrhodamine B hydrazine derived from xanthene dye Rhodamine B is represented by the following reaction process:

[0017]

[0018] Rhodamine B (1) (1 g) was dissolved in anhydrous methanol (40 mL) to form a clear solution. To this solution was added excess hydrazine hydrate (85%, 4mL), heated to reflux with stirring for 6h, then the reaction system was removed with a rotary evaporator to remove the solvent, the residue was recrystallized in methanol-water to obtain 750mg of product rhodamine B hydrazine (2 ), the yield is 78.8%.

[0019] Rhodamine B hydrazine (2) (200mg) and triethylamine (400μL) were dissolved in 5mL THF / 1mL water, and benzoyl chloride (3) (300μL) was dissolved in THF (5mL) to form clear solutions. At 0 Under stirring at °C, drop the THF solution of benzoyl chloride into the solution of rhodamine B hydrazine. After the addition is complete, the system is stirred overnight for rea...

Embodiment 2

[0022] Example 2: N-benzoyl rhodamine B hydrazine is used as an analytical reagent to detect hypochlorite by absorption

[0023] Add 100μl of reagent—N-benzoylrhodamine B hydrazine in THF (concentration 1mM) to a 10ml test tube, dilute to 3ml with THF, then add 2ml of secondary deionized water and 3ml of 0.1M Na 2 B 4 O 7 -NaOH buffer solution (pH=12.2), finally add different amounts of sodium hypochlorite mother liquor and dilute the volume to 10ml with secondary deionized water (make the sodium hypochlorite concentration in the system 1-100μM respectively), shake and react at room temperature for 30min. Use the same operation but no reagents—N-benzoylrhodamine B hydrazine and sodium hypochlorite solution as a blank to measure the absorption spectrum of the reaction system.

[0024] figure 2 It is the relationship between the concentration of sodium hypochlorite and the absorption spectrum of the reaction system (inset figure: the linear relationship between the absorbance of t...

Embodiment 3

[0030] Example 3. Fluorescence detection of hypochlorite with N-benzoyl rhodamine B hydrazine as an analytical reagent

[0031] Add 100μL of the reagent—N-benzoylrhodamine B hydrazine mother solution (1mM THF solution) into a 10mL test tube, dilute to 3mL with THF, then add 2mL secondary deionized water and 3mL 0.1M Na 2 B 4 O 7 -NaOH buffer solution (pH=12.2), and finally add different amounts of sodium hypochlorite mother liquor and dilute the volume to 10 mL with secondary deionized water, shake and react for 30 minutes at room temperature, and measure the fluorescence spectrum of the reaction system.

[0032] image 3 Is the relationship between the concentration of sodium hypochlorite and the fluorescence spectrum of the reaction system (embedded figure: the linear relationship between the fluorescence intensity of the reaction system and the concentration of sodium hypochlorite, λ ex / em =520 / 578nm). Such as image 3 As shown, the excitation and emission wavelengths of the s...

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Abstract

The invention discloses N-benzoyl rhodamine B hydrazide, a method for making the same and an application of the same. The structure of the N-benzoyl rhodamine B hydrazine is shown in formula I. Due to having great molar absorptivity and high fluorescence quantum yield, xanthene dye is an excellent matrix of an optical probe. The xanthene dye derivative-N-benzoyl rhodamine B hydrazide can be selectively reacted with hypochlorite to carry out chromogenic and fluorescence opening reaction; therefore, a system with excellent optical performance can be generated by colorless matter; moreover, detection can be carried out through both a light absorption method and a fluorescence method. In addition, when the N-benzoyl rhodamine B hydrazide is used to detect hypochlorite, high detection sensitivity can be obtained and the detection can be completed just through adopting a small amount of samples, thereby broadening the application range of the method.

Description

Technical field [0001] The invention relates to N-benzoylrhodamine B hydrazine and a preparation method thereof, and the application of N-benzoylrhodamine B hydrazine in detecting hypochlorite ion. Background technique [0002] The current methods for detecting hypochlorite mainly include sodium thiosulfate titration (HG / T 2498-93), o-tolidine colorimetric method (GB 5750-85) and tetramethylbenzidine (TMB) colorimetric method, etc. . The main disadvantages of these methods are poor selectivity and susceptibility to interference, and their application is greatly restricted. [0003] As an important fluorescent material, xanthene dyes are widely used in the design and synthesis of various analytical reagents due to their excellent absorption and fluorescence properties (J. Am. Chem. Soc. 1997, 119: 7386-7387). Using xanthene dyes as the matrix and modified with special reactive groups, the high sensitivity of xanthene dyes and the high selectivity of special groups can be combined ...

Claims

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Application Information

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IPC IPC(8): C07D491/10G01N21/64G01N21/31
Inventor 马会民陈新启
Owner INST OF CHEM CHINESE ACAD OF SCI
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