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A kind of preparation method and application of water-soluble supramolecular organic cage compound for detecting pyridinium salts in water

A compound and supramolecular technology, applied in organic chemistry, material analysis by observing the impact on chemical indicators, resistance to vector-borne diseases, etc., can solve the problem of inability to timely determine whether the water body contains such toxic substances and ionic compounds Low sensitivity, inability to have universality and other problems, to achieve the effect of convenient large-scale storage, good immediacy, and high yield

Active Publication Date: 2022-07-12
ZHEJIANG ZHENENG TECHN RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, domestic and foreign methods for detecting pyridinium salts in water are relatively limited and the detection cost is high, and they are not yet universal. For example, the common method for the detection of paraquat is liquid chromatography-mass spectrometry / mass spectrometry. Due to the high polarity and poor mobility in the reversed-phase chromatographic column, there are problems such as low sensitivity and poor reproducibility in the detection process. These limitations often make it impossible for people to judge whether the water contains such toxic substances in time

Method used

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  • A kind of preparation method and application of water-soluble supramolecular organic cage compound for detecting pyridinium salts in water
  • A kind of preparation method and application of water-soluble supramolecular organic cage compound for detecting pyridinium salts in water
  • A kind of preparation method and application of water-soluble supramolecular organic cage compound for detecting pyridinium salts in water

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Effect test

Embodiment 1

[0065] Embodiment 1 of the present application provides a preparation method of a water-soluble supramolecular organic cage compound for detecting pyridinium salts in water:

[0066] Step 1. Synthesis of compound S1.

[0067] 5-Bromo-2-methylbenzoic acid (15g, 70mmol) was weighed and dissolved in 200ml methanol and placed in a 500ml round-bottomed flask, and 10ml of concentrated sulfuric acid (98% and above) was slowly added in batches, followed by heating at 333K. Stirred for 18h, cooled to room temperature, rotary-evaporated (323~333K, 150~200mbar) to remove methanol, the remaining viscous crude product was redissolved in 200ml of ethyl acetate, followed by saturated brine (about 100ml) several times (3~5 times) ) washed the organic phase to remove residual sulfuric acid, then dried with anhydrous sodium sulfate and filtered, and spin-dried the organic solvent to obtain compound S1 (14.1 g, 88%), of which 88% was the conversion rate of reactant to product. like image 3 As...

Embodiment 2

[0086] On the basis of Example 1, Example 2 of the present application provides a preparation method of organic cage compound TFC-2. Example 2 uses the same precursor molecule compound S6 as in Example 1, and its synthesis steps are not described here.

[0087] Synthesis of organic cage compound TFC-2:

[0088] Compound S6 (10 mg, 0.022 mmol) was dispersed in 5 ml D 2 In O, dissolve 1,3,5-benzenetrimethylamine (15 mg, 0.1 mmol) to 1 ml D 2 Shake well in O, dissolve NaOH (13mg, 0.33mmol) to 1mlD 2 Shake well in O, pipette 200 μl of NaOH solution into compound S6 suspension with ultrasonic vibration until the solution becomes clear (40-80KHz, 30-60s), and then pipet 180 μl of tris(2-aminoethylamine) solution In the clear solution of compound S6, the heavy aqueous solution of TFC-1 was obtained after reacting at 313K for 1 h. 1 HNMR (400MHz, D 2 O): δ=8.61(s, 6H), 7.94(s, 6H), 7.86(s, 6H), 7.35(d, J=7.6Hz, 6H), 7.29(d, J=6.4Hz, 6H), 7.23(d, J=7.6Hz, 6H), 7.13(s, 6H), 6.85(d...

Embodiment 3

[0090] Embodiment 3, TFC-1 is used for the qualitative detection of pyridinium salt compounds

[0091] On the basis of Example 1, this example adopts the organic cage compound synthesized in Example 1, and according to the above steps, the concentration of TFC-1 obtained is 10 -4 mol / L aqueous solution (such as Figure 10 (a)), use a pipette to pipette 10μl of paraquat liquid into 10ml of water and shake well, then pipette 50μl of prepared paraquat aqueous solution and add it to 1ml of TFC-1 aqueous solution and shake well, the color of the liquid instantly changes from colorless to red (as Figure 10 (b)), it can be qualitatively indicated that the test sample contains pyridinium salt compounds.

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Abstract

The invention relates to a preparation method of a water-soluble supramolecular organic cage compound for detecting pyridinium salts in water, comprising the steps of: synthesizing a compound S1, wherein the compound S1 is methyl 5-bromo-2-methylbenzoate; Synthesis compound S2, wherein compound S2 is 5-bromo-2-(dibromomethyl) methyl benzoate. The beneficial effects of the invention are: qualitative and quantitative analysis of water samples containing pyridinium salts is carried out, the input cost is greatly reduced, and the raw materials are all commercially available and inexpensive. In addition, it is ready to use, with high flexibility and good immediacy; the raw materials of caged compounds for detection are easy to synthesize, and the products in each step of the synthesis reaction are easy to separate and have high yields, and the chemical properties are stable, which is convenient for large-scale storage; When qualitative, the apparent phenomenon is obvious and the color changes significantly; when quantitative, the sensitivity is high and the repeatability is good, and there is no need to add any additional agents, which is a truly environmentally friendly and green detection method.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of supramolecular main bodies, and in particular relates to a preparation method and application of a water-soluble supramolecular organic cage compound used for detecting pyridinium salts in water. Background technique [0002] Since the first synthesis of crown ethers by Pedersen [Pedersen, C.J.J.Am.Chem.Soc. 1967, 89, 7017-7036.], supramolecular chemistry has developed rapidly as a new field, and various host molecules with different functions have been continuously report it. Weak interactions in supramolecular chemistry include van der Waals forces, hydrogen bonds, electrostatic interactions, π-π stacking, hydrophobic interactions, and free radical interactions. Supramolecular chemistry has a wide range of applications in the fields of host-guest recognition, reaction catalysis, material separation, new material synthesis, and drug delivery and release. [0003] Pyridine c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/08G01N21/33G01N21/79
CPCC07D487/08G01N21/79G01N21/33Y02A50/30
Inventor 张驰陈彪冯向东邬东立雷石宜张贺黄斐鹏吴贤豪陈雨帆梁成思徐浩然陈臻余一凡王维平童小忠
Owner ZHEJIANG ZHENENG TECHN RES INST
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