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N-(2,4-dinitrophenyl)-rhodamine B hydrazide and preparation method and application thereof

A compound and fluorescent probe technology, applied in the field of rhodamine B derivatives and its preparation, can solve the problems of indistinguishable, easy to form interference, short absorption and emission wavelengths, etc.

Inactive Publication Date: 2014-09-24
NAT RESERACH CENT OF GEOANALYSIS +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Optical sensors that can be used for copper ion recognition Although there have been some reports, such as Chereddy et al. (Dyes and Pigments, 2011, 91(3):378-382) reported a Cu ion containing bisrhodamine B group 2+ Optical sensor; Swamy et al. (Chemical Communications, 2008, 45:5915-5917) constructed a monoboronic acid-rhodamine B conjugated Cu 2+ Optical sensor, but its sensitivity is slightly worse, when adding 100 times the equivalent concentration of Cu 2+ , the fluorescence intensity was only increased by 6.4 times; Kaur et al. (Chemical Communications, 2002, 2840-2841) synthesized a Cu with anthracene group 2+ Optical sensor, but the absorption and emission wavelengths are relatively short, which is prone to interference; Yu et al. (Chemistry-A European Journal, 2008, 14(23):6892-6900) reported a fluorescence-enhanced Cu 2+ Optical sensor, however, this sensor cannot significantly differentiate Cu 2+ and Hg 2+

Method used

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  • N-(2,4-dinitrophenyl)-rhodamine B hydrazide and preparation method and application thereof
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  • N-(2,4-dinitrophenyl)-rhodamine B hydrazide and preparation method and application thereof

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Embodiment 1

[0031] Example 1. Preparation of optical sensor molecule N-(2,4-dinitrophenyl)-rhodamine B hydrazide (DNPRH)

[0032] The reaction process is as figure 1 As shown, the specific method is as follows: Rhodamine B (formula II, 400.0 mg, 0.90 mmol) was dissolved in 10 mL of 1,2-dichloroethane, and 0.8 mL of phosphorus oxychloride was slowly added dropwise to it. The mixed system was heated to reflux for 4 hours under stirring, and then the solvent was evaporated under reduced pressure to obtain rhodamine B acid chloride (formula III) in a purple-red oily state. The crude acid chloride was directly added to 10 mL of acetonitrile to form a solution without purification. Then at room temperature (20-25°C), within 30min, the solution was added dropwise to 30mL 2,4-dinitrophenylhydrazine (0.60g, 3.0mmol) and triethylamine (1.6mL, 11.6mmol ) in acetonitrile solution. Stirring was continued at room temperature (20-25°C) for 6 h, and the solvent was evaporated under reduced pressure to...

Embodiment 2

[0035] Example 2, N-(2,4-dinitrophenyl)-rhodamine B hydrazide (DNPRH) is used as an analytical reagent for Cu 2+ Absorbance detection

[0036] 1. N-(2,4-dinitrophenyl)-rhodamine B hydrazide on Cu 2+ Sensitivity for absorbance detection

[0037] Add 500 μL of ethanol solution of reagent-N-(2,4-dinitrophenyl)-rhodamine B hydrazide (concentration 1mM) into a 50mL volumetric flask, dilute to 50mL with ethanol, and use it as a dilution of the mother liquor ( Concentration 10 μM). Take 3mL of the above mother liquor dilution respectively, and add an appropriate volume of Cu 2+ stock solution (CuCl 2 solution) (concentration 1mM), so that Cu in the system 2+ Concentrations were 1 ~ 15μM (concentration gradient of 1μM). After reacting at room temperature (20-25°C) for 40min, transfer 3mL of the reaction solution to a 1cm quartz cuvette, use ethanol as a blank, and measure the ultraviolet absorption spectrum. image 3 for Cu 2+ The relationship between the concentration and the...

Embodiment 3

[0040] Example 3, N-(2,4-dinitrophenyl)-rhodamine B hydrazide (DNPRH) is used as an analytical reagent for Cu 2+ Perform fluorescence detection

[0041] 1. N-(2,4-dinitrophenyl)-rhodamine B hydrazide on Cu 2+ Sensitivity for fluorescence detection

[0042] Add 500 μL of ethanol solution of reagent-N-(2,4-dinitrophenyl)-rhodamine B hydrazide (concentration 1mM) into a 50mL volumetric flask, dilute to 50mL with ethanol, and use it as a dilution of the mother liquor ( Concentration 10 μM). Take 3mL of the above mother liquor dilution respectively, and add an appropriate volume of Cu 2+ stock solution (CuCl 2 solution) (concentration 1mM), so that Cu in the system 2+ Concentrations were 1 ~ 15μM (concentration gradient of 1μM). Measure the fluorescence spectrum of the reaction system after reacting at room temperature (20-25°C) for 40 minutes.

[0043] Figure 5 for Cu 2+ The relationship between the concentration and the fluorescence spectrum of the reaction system (the ...

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Abstract

The invention discloses N-(2,4-dinitrophenyl)-rhodamine B hydrazide and a preparation method and an application of the N-(2,4-dinitrophenyl)-rhodamine B hydrazide. The rhodamine B derivative provided by the invention is N-(2,4-dinitrophenyl)-rhodamine B hydrazide, the structural formula of which is I. The N-(2,4-dinitrophenyl)-rhodamine B hydrazide, is colorless and free from fluorescence, but can selectively react with Cu<2+> ions in chromogenic and fluorescent opening reaction. The colorless substance generates a system with excellent optical performance, so that the detection sensitivity and selectivity of Cu<2+> ions are greatly improved. Therefore, the N-(2,4-dinitrophenyl)-rhodamine B hydrazide is appropriate for high selectivity and high sensitivity detection for the Cu<2+> ions. Detection can be carried out by a light absorption spectrum and a fluorescence spectrum. (Formula I is shown in the specification).

Description

technical field [0001] The present invention relates to a rhodamine B derivative and its preparation method and application, in particular to N-(2,4-dinitrophenyl)-rhodamine B hydrazide and its preparation method and its ability to detect Cu(II) in the application. Background technique [0002] Heavy metals and transition metals widely exist in nature, and some of these elements have very important functions in the life process, such as copper plays an important role in regulating tumor angiogenesis factors, and zinc is widely involved in cell growth and development, gene transcription, neurotransmission and other important life processes; other elements are extremely toxic to organisms at lower concentrations, such as lead can cause lesions in the digestive system, nervous system and heart. Therefore, it is of great significance to establish fast and efficient detection methods for heavy metals and transition metals in life sciences, environmental sciences, medical science...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107G01N21/31G01N21/64
Inventor 王晓春陈新启郑禾钟近艺盖希杰
Owner NAT RESERACH CENT OF GEOANALYSIS
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