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A preparing method of N-(2,4-dinitrophenyl)rhodamine B-hydrazide and an application of the N-(2,4-dinitrophenyl)rhodamine B-hydrazide for detection of Cu(II)

A technology of dinitrophenylhydrazine and acid chloride, applied in chemical instruments and methods, measuring devices, color/spectral characteristic measurement, etc., can solve the problems of short absorption and emission wavelengths, poor sensitivity, and inability to distinguish significantly.

Inactive Publication Date: 2015-01-07
NAT RESERACH CENT OF GEOANALYSIS +1
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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+

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  • A preparing method of N-(2,4-dinitrophenyl)rhodamine B-hydrazide and an application of the N-(2,4-dinitrophenyl)rhodamine B-hydrazide for detection of Cu(II)
  • A preparing method of N-(2,4-dinitrophenyl)rhodamine B-hydrazide and an application of the N-(2,4-dinitrophenyl)rhodamine B-hydrazide for detection of Cu(II)
  • A preparing method of N-(2,4-dinitrophenyl)rhodamine B-hydrazide and an application of the N-(2,4-dinitrophenyl)rhodamine B-hydrazide for detection of Cu(II)

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Embodiment 1

[0032] Example 1, Preparation of optical sensor molecule N-(2,4-dinitrophenyl)-rhodamine B hydrazide (DNPRH)

[0033] The reaction process is as figure 1As 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 thereto. The mixed system was heated to reflux for 4 h 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 for 6 h at room temperature (20-25° C.), and the solvent was distilled off under reduced pressure...

Embodiment 2

[0036] Embodiment 2, N-(2,4-dinitrophenyl)-rhodamine B hydrazide (DNPRH) is as analytical reagent to Cu 2+ Absorbance detection

[0037] 1. N-(2,4-dinitrophenyl)-rhodamine B hydrazide on Cu 2+ Sensitivity for absorbance detection

[0038] Add 500 μL of reagent—N-(2,4-dinitrophenyl)-rhodamine B hydrazide ethanol solution (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+ The concentrations were 1-15 μM (the concentration gradient was 1 μM). After reacting at room temperature (20-25° C.) for 40 minutes, transfer 3 mL of the reaction solution to a 1 cm quartz cuvette, and use ethanol as a blank to measure the ultraviolet absorption spectrum. image 3 for Cu 2+ The relationship between the concentrat...

Embodiment 3

[0041] Embodiment 3, N-(2,4-dinitrophenyl)-rhodamine B hydrazide (DNPRH) is as analytical reagent to Cu 2+ Perform fluorescence detection

[0042] 1. N-(2,4-dinitrophenyl)-rhodamine B hydrazide on Cu 2+ Sensitivity for fluorescence detection

[0043] Add 500 μL of reagent—N-(2,4-dinitrophenyl)-rhodamine B hydrazide ethanol solution (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+ The concentrations were 1-15 μM (the concentration gradient was 1 μM). After reacting at room temperature (20-25° C.) for 40 minutes, the fluorescence spectrum of the reaction system was measured.

[0044] Figure 5 for Cu 2+ Concentration and reaction system fluorescence spectrum relationship diagram (reaction system...

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Abstract

A preparing method of N-(2,4-dinitrophenyl)rhodamine B-hydrazide and an application of the N-(2,4-dinitrophenyl)rhodamine B-hydrazide for detection of Cu(II) are disclosed. The preparing method includes a step of reacting rhodamine B acid chloride and 2,4-dinitrophenylhydrazine to generate the N-(2,4-dinitrophenyl)rhodamine B-hydrazide. The N-(2,4-dinitrophenyl)rhodamine B-hydrazide itself is free of color and fluorescence, but can generate coloring and fluorescence generating reactions selectively with Cu<2+>, so that a colorless substance is turned into a system with excellent optical properties, and detection sensitivity and selectivity for the Cu<2+> are largely enhanced. Accordingly, the N-(2,4-dinitrophenyl)rhodamine B-hydrazide is suitable for high-selectivity and high-sensitivity detection of the Cu<2+>. The detection can be performed by a light absorption spectrum method and a fluorescence spectrum method.

Description

[0001] This application is the application number 201210323481.0, the application date is September 04, 2012, and the invention name is "N-(2,4-dinitrophenyl)-rhodamine B hydrazide and its preparation method and application" Divisional application. technical field [0002] The invention relates to a preparation method of N-(2,4-dinitrophenyl)-rhodamine B hydrazide and its application for detecting Cu(II). Background technique [0003] 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1088G01N21/33G01N21/6402
Inventor 陈新启王晓春郑禾钟近艺盖希杰
Owner NAT RESERACH CENT OF GEOANALYSIS
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