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Monomers and polymers for recognition of halide anions and methods of preparation

An anion and monomer technology, applied in the preparation of organic compounds, chemical instruments and methods, preparation of carboxylic acid amides, etc., can solve problems such as lack of synergistic identification of anions

Inactive Publication Date: 2017-01-04
TIANSHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many research reports on functional receptor molecules that combine and recognize anions by hydrogen bonds or halogen bonds alone, but there are no patents on functional organic small molecules and their polymers that recognize anions based on the above two weak interactions at the same time. material

Method used

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  • Monomers and polymers for recognition of halide anions and methods of preparation
  • Monomers and polymers for recognition of halide anions and methods of preparation
  • Monomers and polymers for recognition of halide anions and methods of preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Dissolve 1.0 mmol of p-aminophenylacetylene, 1.3 mmol of pentafluorobenzoic acid and 0.2 mmol of N,N-dimethyl-4-aminopyridine in 5 ml of anhydrous CH 2 Cl 2 In, then add 1.5mmol of dimethylaminopropyl ethyl carbonamide hydrochloride (EDC-HCl), 23 DEG C of stirring reaction 24h. react with CH 2 Cl 2 as a solvent, the reaction system was washed with water, the organic layer was separated, and the aqueous layer was washed with CH 2 Cl 2 Extracted 3 times, the obtained organic layers were combined and washed with concentrated brine, the organic layer was separated and washed with anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated by distillation under reduced pressure. Using ethyl acetate as the eluent, the crude product concentrate was separated and purified on silica gel column chromatography to obtain the target product N -(p-ethynyl)-phenyl-2-X-tetrafluorobenzamide (pale yellow crystals, yield 92%).

[0056] Under the protection of Ar ...

Embodiment 2

[0058] Dissolve 1.0 mmol of p-aminophenylacetylene, 1.3 mmol of 2-chloro-tetrafluorobenzoic acid and 0.2 mmol of N,N-dimethyl-4-aminopyridine in 5 ml of anhydrous CH 2 Cl 2 In, then add 1.5mmol of dimethylaminopropyl ethyl carbonamide hydrochloride (EDC-HCl), 25 DEG C of stirring reaction 26h. react with CH 2 Cl 2 as a solvent, the reaction system was washed with water, the organic layer was separated, and the aqueous layer was washed with CH 2 Cl2 Extracted 3 times, the obtained organic layers were combined and washed with concentrated brine, the organic layer was separated and washed with anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated by distillation under reduced pressure. Using ethyl acetate as the eluent, the crude product concentrate was separated and purified on silica gel column chromatography to obtain the target product N -(p-ethynyl)-phenyl-2-chloro-tetrafluorobenzamide (pale yellow crystals, yield 92%).

[0059] Under the prote...

Embodiment 3

[0061] Dissolve 1.0 mmol of p-aminophenylacetylene, 1.3 mmol of 2-I-tetrafluorobenzoic acid and 0.2 mmol of N,N-dimethyl-4-aminopyridine in 5 ml of anhydrous THF, and then add 1.5 mmol of di Methylaminopropyl ethyl carbonamide hydrochloride (EDC-HCl), stirred at 23°C for 30h. The reaction used THF as a solvent, distilled the reaction system under reduced pressure, diluted the distillation residue with 50 ml of ethyl acetate, washed with 20 ml of water and 20 ml of hydrochloric acid (1 M aq. Water Na 2 SO 4 After drying and filtering, the filtrate was concentrated by distillation under reduced pressure. Using ethyl acetate as the eluent, the crude product concentrate was separated and purified on silica gel column chromatography to obtain the target product N -(p-ethynyl)-phenyl-2-X-tetrafluorobenzamide (pale yellow crystals, about 92.5% yield).

[0062] Under the protection of Ar gas, the 2.69mmol N -(p-ethynyl)-phenyl-2-I-tetrafluorobenzamide monomer was dissolved in a S...

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Abstract

The invention discloses a monomer N-(p-acetenyl)-phenyl-2-X-tetrafluorobenzamide (X=F, Cl, Br and I) for identifying halogen anions, a polymer, and a method for preparing the monomer and the polymer. The method comprises the following steps: by taking 4-ethynylaniline and hexafluorobenzoic acid as main initial raw materials, taking N,N-dimethyl-4-aminopyridine as a catalyst, finally synthesizing a target small molecule compound N-(p-acetenyl)-phenyl-2-X-tetrafluorobenzamide; and by taking a precious metal complex Rh+(2,5-nbd)[(eta6-C6H5)B-(C6H5)3] (triphenyl-eta6-phenylboron-2,5-norborneol diene rhodium, Rh(nbd)BPh4) as a catalyst, thereby obtaining the poly-N-(p-acetenyl)-phenyl-2-X-tetrafluorobenzamide by virtue of a coordination polymer orientation method. The obtained small molecule monomer and polymer molecular structures simultaneously contain hydrogen bond donors and halogen bond donors, and the monomer and polymer can identify the halogen anions by virtue of coordination of hydrogen bonds and halogen bonds. Meanwhile, the preparation method has the advantages of the reaction conditions are mild, the reaction process is simple, the method is easy to control, the yield of the obtained product is high and the like.

Description

technical field [0001] The invention relates to the technical field of monomers and polymers having hydrogen bonds and halogen bond donors for recognizing halide anions, in particular to a kind of monomer for recognizing halide anions N -(p-ethynyl)-phenyl-2-X-tetrafluorobenzamide (X=F, Cl, Br, I) monomer and its polymer preparation method and application. Background technique [0002] Anion recognition with high selectivity, strong affinity, high sensitivity and unique response plays an extremely important role in nature or anion sensing process, although the research on anion recognition has made encouraging progress in recent years, but in Artificial molecular ion recognition, molecular design and synthesis of anion receptors are still very challenging research contents in the field of chemistry. Therefore, the host-guest chemistry of anion recognition and its application research is one of the research hotspots and focuses in the field of supramolecular chemistry. . ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/65C07C231/02C08F138/00G01N21/78
Inventor 朱元成刘艳芝袁焜吕玲玲刘流王晓峰
Owner TIANSHUI NORMAL UNIV
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