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Monomer with anion recognizing function, oligomer and preparation method thereof

A technology for anion recognition and function, applied in the field of preparation of monomers and oligomers

Inactive Publication Date: 2015-06-03
TIANSHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the functional group design of anion acceptors is still based on various -NH hydrogen bond donors, and the structural design of anion recognition by anion-π weak interaction is mainly used for the development of small molecule acceptors, and has not been studied yet. The introduction of anion-π into the synthesis of oligomer acceptors, and the introduction of hydrogen bond donors and anion-π donors into the synthesis of molecular skeleton structures at the same time has not been reported to study the weak synergy between hydrogen bonds and anion-π Recognition of anions by interactions

Method used

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  • Monomer with anion recognizing function, oligomer and preparation method thereof
  • Monomer with anion recognizing function, oligomer and preparation method thereof
  • Monomer with anion recognizing function, oligomer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0052] Degassed DMF / NET with 2-amino-5-iodobenzyl alcohol 2mmol, triphenylphosphine 33umol, bis-(triphenylphosphine)-dichloropalladium 16umol, 48umol CuI 3 (V / V, 2.8ml / 8ml) solution in N 2 Add it into a three-necked flask containing 3.4mmol trimethylsilylacetylene under atmosphere, stir and react at room temperature for 22h, distill the reaction system under reduced pressure, dissolve the residue with dichloromethane, wash with hydrochloric acid solution, and wash the organic layer with anhydrous MgSO 4 After drying, filtration, vacuum distillation and concentration, separation and purification on silica gel column chromatography with ethyl acetate / n-hexane (1 / 2, v / v) as eluent, the intermediate product 2-amino-5-trimethyl Silynyl benzyl alcohol (light yellow liquid, weight 0.35g, yield 90%).

[0053]Dissolve 1.8mmol of 2-amino-5-trimethylsilynyl benzyl alcohol in a mixed solvent of 30.6ml of MeOH / THF (V / V, 0.6ml / 30ml), and add 1M tetrabutylammonium fluoride THF solution 0.6...

Embodiment 2

[0058] 2-amino-5-iodobenzyl alcohol 2mmol, triphenylphosphine 33umol, bis-(triphenylphosphine)-dichloropalladium 16umol, CuI (9.1mg, 48umol) degassed DMF / NET 3 (V / V, 2.8ml / 8ml) solution in N 2 Add it into a three-necked flask containing 3.4mmol trimethylsilylacetylene under atmosphere, stir and react at room temperature for 24h, distill the reaction system under reduced pressure, dissolve the residue with dichloromethane, wash with hydrochloric acid solution, and wash the organic layer with anhydrous MgSO 4 After drying, filtration, vacuum distillation and concentration, separation and purification on silica gel column chromatography with ethyl acetate / n-hexane (V / V, 1 / 2) as eluent, the intermediate product 2-amino-5-trimethyl Silynyl benzyl alcohol (light yellow liquid, weight 0.55g, yield 91%).

[0059] Dissolve 1.8mmol of 2-amino-5-trimethylsilynyl benzyl alcohol in 30.6ml of a mixed solvent of MeOH / THF (V / V, 0.6ml / 30ml), and add 1M tetrabutylammonium fluoride in THF Solu...

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Abstract

The invention discloses a N-p-nitrophenyl-N-(p-acetenyl-2-pentafluorobenzoic acid benzoyloxycarbonyl)-phenyl-urea monomer, an oligomer and a preparation method thereof. As a target product of the technology, the N-p-nitrophenyl-N-(p-acetenyl-2-pentafluorobenzoic acid benzoyloxycarbonyl)-phenyl-urea and the oligomer structure have urea structure units which can be used as hydrogen-bond donors, also have aromatic-ring structure units which can be used as anion-n donors, and when the urea structure units and the aromatic-ring structure units are combined with the anions, the synergy on the space geometry is achieved, i.e., the N-p-nitrophenyl-N-(p-acetenyl-2-pentafluorobenzoic acid benzoyloxycarbonyl)-phenyl-urea can recognize anions by the synergistic effect of two weak bonds such as hydrogen bonds and anion-n simultaneously, the target-product oligomer of the N-p-nitrophenyl-N-(p-acetenyl-2-pentafluorobenzoic acid benzoyloxycarbonyl)-phenyl-urea has the same space geometrical structure with the monomer thereof, i.e., a plurality of anions also can be recognized and combined by the synergistic effect of the two weak bonds such as the hydrogen bonds and the anion-n.

Description

technical field [0001] The invention belongs to the technical field of hydrogen bond and π-electron cooperative recognition of anions, and specifically relates to a monomer and an oligomer based on a hydrogen bond and π-electron cooperative recognition of anions, and the invention also relates to the preparation of the monomer and oligomer methods and applications. Background technique [0002] In nature or life process, the anion recognition process plays an extremely important role, such as the processing of information by the retina, the metabolism of arginine in the liver and kidney, and many other important biochemical processes are controlled by anions. In artificial systems, anion recognition is used to precisely control the formation of pseudorotaxanes, prepare supramolecular capsules, and manipulate the morphological evolution of molecular machines and crystals, especially in molecular machines and molecular storage materials, how to control the combination of host ...

Claims

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Application Information

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IPC IPC(8): C07C275/32C07C273/18
Inventor 刘艳芝朱元成袁焜吕玲玲刘流王晓峰
Owner TIANSHUI NORMAL UNIV
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