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Title: UO{sub 2}-salenes: Neutral receptors for anions with a high selectivity for dihydrogen phosphate

Abstract

The design and synthesis of neutral macrocyclic receptors that complex cations in apolar solvents with a high degree selectivity are based on the ability to organize nucleophilic binding sites (Lewis bases) in a complementary array. Although macrocycles with quaternary ammonium salts are known to complex anions, selectivity is not simply introduced. Macrocyclic and acyclic ligands that contain Lewis acidic binding sites such as boron, silicon, tin, and mercury bind anions, but these structures lack the possibility of subtle structural variation that is the basis for the selectivity in cation complexation. In this communication we report a novel class of neutral receptors for anions that contain an immobilized Lewis acidic binding site (UO{sub 2}){sup 2+} and in which there are ample opportunities to introduce specific secondary binding sites. This concept leads to high thermodynamic stabilities combined with high selectivities. Neutral anion receptors are very important for application in sensors and membrane transport experiments. This unique combination of a Lewis acidic uranyl center and the presence of amide NH groups which can form a favorable H-bond with a coordinated anion guest, in a preorganized receptor, can lead to highly specific anion recognition. 20 refs., 2 figs., 1 tab.

Authors:
; ;  [1]
  1. Univ. of Twente, Enschede (Netherlands); and others
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
269188
Resource Type:
Journal Article
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 114; Journal Issue: 24; Other Information: PBD: 18 Nov 1992
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; URANIUM OXIDES; CHEMICAL PREPARATION; STRUCTURAL CHEMICAL ANALYSIS; URANIUM COMPLEXES; LEWIS BASES; MEMBRANE TRANSPORT; RECEPTORS

Citation Formats

Rudkevich, D M, Stauthamer, W P.V., and Verboom, W. UO{sub 2}-salenes: Neutral receptors for anions with a high selectivity for dihydrogen phosphate. United States: N. p., 1992. Web. doi:10.1021/ja00050a064.
Rudkevich, D M, Stauthamer, W P.V., & Verboom, W. UO{sub 2}-salenes: Neutral receptors for anions with a high selectivity for dihydrogen phosphate. United States. doi:10.1021/ja00050a064.
Rudkevich, D M, Stauthamer, W P.V., and Verboom, W. Wed . "UO{sub 2}-salenes: Neutral receptors for anions with a high selectivity for dihydrogen phosphate". United States. doi:10.1021/ja00050a064.
@article{osti_269188,
title = {UO{sub 2}-salenes: Neutral receptors for anions with a high selectivity for dihydrogen phosphate},
author = {Rudkevich, D M and Stauthamer, W P.V. and Verboom, W},
abstractNote = {The design and synthesis of neutral macrocyclic receptors that complex cations in apolar solvents with a high degree selectivity are based on the ability to organize nucleophilic binding sites (Lewis bases) in a complementary array. Although macrocycles with quaternary ammonium salts are known to complex anions, selectivity is not simply introduced. Macrocyclic and acyclic ligands that contain Lewis acidic binding sites such as boron, silicon, tin, and mercury bind anions, but these structures lack the possibility of subtle structural variation that is the basis for the selectivity in cation complexation. In this communication we report a novel class of neutral receptors for anions that contain an immobilized Lewis acidic binding site (UO{sub 2}){sup 2+} and in which there are ample opportunities to introduce specific secondary binding sites. This concept leads to high thermodynamic stabilities combined with high selectivities. Neutral anion receptors are very important for application in sensors and membrane transport experiments. This unique combination of a Lewis acidic uranyl center and the presence of amide NH groups which can form a favorable H-bond with a coordinated anion guest, in a preorganized receptor, can lead to highly specific anion recognition. 20 refs., 2 figs., 1 tab.},
doi = {10.1021/ja00050a064},
journal = {Journal of the American Chemical Society},
number = 24,
volume = 114,
place = {United States},
year = {1992},
month = {11}
}