Compound based on Rhodamine B and thiobisethylamine as well as preparation method and application thereof
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 wide detection range
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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 (300 MHz, 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....
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 shown in 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 a new absorption peak at 560 nm in the UV-Vis absorption spectrum of RMTE (Figure 1 left panel), the fluorescence was significantly enhanced by 33.9 times (Figure 1 right panel).
[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 shown in 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, slit width...
Embodiment 3
[0043] Embodiment three: RMTE and Hg 2+ concentration relationship
[0044] Figure 4 shows the samples 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. As can be seen from the left figure of Figure 4, with the 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 ...
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