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Diaminomaleonitrile derivative, preparation method and application thereof
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A technology for diaminomaleonitrile and derivatives, applied in the field of diaminomaleonitrile derivatives and their preparation, can solve the problems of high cost, need complex instruments and the like, and achieve high selectivity, good selectivity and high identification strength Effect
Inactive Publication Date: 2015-02-04
GUANGDONG UNIV OF TECH
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Embodiment 1
[0071] Embodiment 1: the synthesis of compound 1:
[0072] Add 4.6mmol of p-fluorobenzaldehyde and 4.6mmol of diaminomaleonitrile successively in 20mL of absolute ethanol, stir to dissolve, heat the mixture to reflux at 80°C for 8 hours to obtain a yellow precipitate, filter and wash with ethanol 3 times, then washed 3 times with purified water, and dried, the yield was 87%. 1 H NMR (400 MHz, DMSO)δ 8.35-7.82 (m, 5H), 7.40-7.21 (m, 2H). 19 F NMR (376 MHz, DMSO) δ: -108.25 (s, J = 8.9, 5.8 Hz). EI-MS m / z: 214.
[0073]
[0074] Compound 1
Embodiment 2
[0075] Embodiment 2: the synthesis of compound 2:
[0076] The method is the same as in Example 1, except that 2,3,4-trimethoxybenzaldehyde is used instead of p-fluorobenzaldehyde to obtain a yellow product with a yield of 73%. 1 H NMR (400 MHz, cdcl 3 ) δ 8.70 (s, 1H), 7.72 (d, J = 8.3 Hz, 1H), 7.26 (s, 1H), 6.72 (d, J = 9.3 Hz, 1H), 5.11 (s, 2H), 4.01-3.83 (m, 9H). ESI-MS m / z: 286.9000 ([M ＋ H] + )
[0077]
[0078] Compound 2
Embodiment 3
[0079] Embodiment 3: the synthesis of compound 3:
[0080] The method is the same as in Example 1, except that 4-tert-butylbenzaldehyde is used instead of p-fluorobenzaldehyde to obtain a yellow product with a yield of 87%. 1 H NMR (400 MHz, cdcl 3 ) δ 8.40 (s, 1H), 7.75 (d, J = 7.6 Hz, 2H), 7.48 (d, J = 7.7 Hz, 2H), 5.25 (s, 2H), 1.34 (s, 9H). ESI-MS m / z: 252.9500 ([M ＋ H] + )
[0081]
[0082] Compound 3
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Abstract
The invention discloses a diaminomaleonitrile derivative being characterized in that a structural formula is represented as the formula (I). The invention also discloses a preparation method and an application of the diaminomaleonitrile derivative. A chemical sensor prepared from the diaminomaleonitrile derivative is sensitive in response to mercury ion, is good in selectivity, is high in recognizing intensity and is free of interference of foreign metal ions. Meanwhile, fluorescence of the sensor appears in a visible region when the sensor detects the mercury ion so that existence of the mercury ion can be detected just by naked eyes in a colorimetric analysis manner. The method is high in practical value and has a huge application prospect in quick and simple detection of the mercury ion.
Description
technical field [0001] The present invention relates to the technical field of diaminomaleonitrile derivatives, more specifically, to a diaminomaleonitrile derivative and its preparation method and application. Background technique [0002] Mercury is a chemical substance with severe physiological toxicity. Humans inhale mercury mainly through the enrichment of organisms in the soil and the transmission of the food chain. Brain and kidney, followed by liver, intestinal wall, heart, lung, etc. When the mercury content accumulates in the human body to a certain extent, it will lead to poisoning and even death in severe cases. In addition, mercury can enter the human body through the respiratory tract in the form of vapor. According to reports, if humans inhale 1 to 3 mg / m 3 Acute poisoning will occur if the mercury vapor lasts for several hours. Mercury vapor mainly causes stomatitis and central nervous system damage, and high concentration can also cause kidney damage. [0...
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