Compounds based on rhodamine b and aminoethyl sulfide, methods for their preparation and applications

A technology of aminoethyl sulfide and compounds, applied to the application of mercury ion probes in the detection of mercury ions, based on the field of rhodamine B and aminoethyl sulfide compounds and their preparation, can solve the problem of irreversible mercury ion reactions, Problems such as rare raw materials and difficult synthesis can achieve the effects of industrial application, mild reaction conditions and good application prospects

Active Publication Date: 2018-01-19
SUZHOU UNIV
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Problems solved by technology

[0003] However, the reported rhodamine-based spectral probes have rare raw materials, complex structures, and difficult synthesis, and some can only detect Hg in pure organic solvents (such as absolute ethanol). 2+ , or the anti-interference ability and practicability are not good, and the rhodamine Hg with good comprehensive performance 2+ There are very few spectroscopic probes (see: Xu L, Wang S, Lv YN, Son YA, Cao DR. A highlyselective and sensitive photo switchable fluorescent probe for Hg 2+ based onbisthienylethene-rhodamine 6G dyad and for live cells imaging. Spectrochim. Acta Part A 2014; 128: 567-574; Bhalla V, Tejpal R, Kumar M. Rhodamineappended terphenyl: A reversible “off-on” fluorescent chemosensors for mercury . Actuators B 2010; 151: 180-185; Zhang X, Zhu YY. A new fluorescent chemodosimeter for Hg 2+ -selective detection in aqueous solution based on Hg 2+ -promoted hydrolysis of rhodamine-glyoxylic acid conjugate. Sens. Actuators B2014; 202: 609-614)
In addition, rhodamine Hg 2+ The conversion of the signal of the spectral probe is generally achieved by two methods, one is to add mercury ions, coordinate with the probe and induce the ring opening of the spironolactam, which often responds or delays the reaction to other metal cations; the other Mercury ions activate the thiocarbonyl stoichiometric reaction. The biggest problem is that the reaction of mercury ions is irreversible, so follow-up analysis cannot be performed, probes cannot be reused, and mercury ions cannot be recovered, making it impractical.

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  • Compounds based on rhodamine b and aminoethyl sulfide, methods for their preparation and applications
  • Compounds based on rhodamine b and aminoethyl sulfide, methods for their preparation and applications
  • Compounds based on rhodamine b and aminoethyl sulfide, methods for their preparation and applications

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment one: Hg 2+ Preparation of probe RMTE

[0034] According to the ratio of raw materials in Table 1 (molar ratio of rhodamine B and aminoethyl sulfide) and reaction conditions, with dichloromethane as solvent, N,N-diisopropylethylamine as additive, in N 2 Under protection, stir the reaction, cool to room temperature, remove the solvent by rotary evaporation, and separate by column chromatography, the eluent is methanol / chloroform / petroleum ether, 1 / 12 / 2 (v / v / v), dried to obtain Target product RMTE as yellow solid powder.

[0035] NMR, 1 H NMR (400 MHz, CDCl 3 ), δ / ppm: 1.16 ( t , 12H, J=6.8 Hz), 2.23( t , 2H, J=8 Hz), 2.50 ( t , 2H, J=6.4 Hz), 2.77 ( t , 2H, J=6.4 Hz), 3.27–2.37( m , 10H), 3.66 (s, 2H), 6.27 ( d , 2H, J=6.4 Hz), 6.37 ( d , 2H, J=2.4 Hz), 6.44( s , 2H), 7.08–7.10 ( m , 1H), 7.43–7.46 ( m , 2H), 7.89–7.91 ( m , 1H), 13 C NMR (300MHz, CDCl 3 ), Δ / PPM: 12.35, 29.37, 34.71, 40.24, 40.83, 44.31, 64.69, 97.34,105.62, 107.96, 122.63, 1...

Embodiment 2

[0038] Embodiment two: RMTE to Hg 2+ the response to

[0039] CH at RMTE 3 Add Hg to CN / HEPES buffer solution (1 / 1, v / v, pH=7.05) 2+ , measure the UV-Vis absorption spectrum and fluorescence spectrum before and after adding ions, the results are as follows figure 1 , solvent: CH 3 CN / HEPES buffer solution (1 / 1, v / v, pH=7.05), concentration: 20 μM (RMTE), 200 μM (Hg 2+ ). Excitation wavelength: 520 nm, slit width: 5 nm. Hg 2+ The addition of the RMTE UV-Vis absorption spectrum at 560 nm appears a new absorption peak ( figure 1 Left panel), the fluorescence was significantly enhanced by 33.9 times ( figure 1 right).

[0040] CH at RMTE 3 Add Hg to CN / HEPES buffer solution (2 / 8, v / v, pH=7.05) 2+ , measure the UV-Vis absorption spectrum and fluorescence spectrum before and after adding ions, the results are as follows figure 2 , solvent: CH 3 CN / HEPES buffer solution (2 / 8, v / v, pH=7.05), concentration: 20 μM (RMTE), 200 μM (Hg 2+ ). Excitation wavelength: 520 nm, s...

Embodiment 3

[0043] Embodiment three: RMTE and Hg 2+ concentration relationship

[0044] Figure 4 for containing different concentrations of Hg 2+ UV-Vis absorption spectrum (left) and fluorescence spectrum (right) of RMTE solution, solvent: CH 3 CN / HEPES buffer solution (1 / 99, v / v, pH=7.05), concentration: 20 μM (RMTE), Hg 2+ Concentrations from bottom to top are 0, 10, 20, 30, 40, 60, 80, 100, 120, 140, 160, 180 and 200 μM, insets are RMTE absorbance (A) and Hg at 561 nm, respectively 2+ The relationship between concentration and RMTE fluorescence intensity (F) at 578 nm vs. Hg 2+ The relationship between concentration, excitation wavelength: 520 nm, slit width: 5 nm. from Figure 4 As can be seen from the left figure, with Hg 2+ As the concentration increases, the absorbance of RMTE at 561 nm first increases and then tends to be stable. in Hg 2+ In a wide range of concentrations, the absorbance A and Hg 2+ The concentration has a good linear relationship, and the linear equat...

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Abstract

The invention discloses a compound based on rhodamine B and aminoethyl sulfide, its preparation method and application, which is a novel rhodamine-like Hg2+ colorimetric and fluorescent probe with excellent comprehensive performance and reversible sensing mechanism. Its excellent comprehensive properties include: easy-to-obtain raw materials, simple synthesis method, and simple molecular structure; good selectivity to Hg2+, high sensitivity, strong anti-interference ability, and low cytotoxicity; detection can be carried out in a near-neutral almost pure water buffer solution ; It can effectively detect Hg2+ in ponds and tap water samples; it can detect Hg2+ in HgCl2; the molecule contains an aliphatic primary amino group, which can be further modified by itself or other materials.

Description

technical field [0001] The invention belongs to the technical field of heavy metal ion probes, in particular to a compound based on rhodamine B and aminoethyl sulfide, a preparation method thereof, and the application of the compound as a mercury ion probe in detecting mercury ions. Background technique [0002] Mercury is the second most common toxic heavy metal. Whether it is elemental mercury, inorganic mercury, or organic mercury, it can damage organs such as the kidney, central nervous system, and brain, leading to cognitive and motor dysfunction, and even cancer. If mercury and its compounds exist in natural water bodies, they can easily pollute the water environment and cause harm to a wide range of people. Hg 2+ The most common form of mercury contamination, it is highly water soluble, so its detection is critical. Spectral probes have attracted much attention due to their advantages of simple operation, rapid detection sensitivity, high selectivity, and low cost. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N21/78
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/643G01N21/78
Inventor 徐冬梅洪苗苗
Owner SUZHOU UNIV
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