Sulphate binding by a quinolinyl-functionalised tripodal tris-urea receptor

Yongjing Hao; Chuandong Jia; Shaoguang Li; Xiaojuan Huang; Xiao Juan Yang; Christoph Janiak; Biao Wu

doi:10.1080/10610278.2011.622389

Sulphate binding by a quinolinyl-functionalised tripodal tris-urea receptor

Yongjing Hao, Chuandong Jia, Shaoguang Li, Xiaojuan Huang, Xiao Juan Yang, Christoph Janiak, Biao Wu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A quinolinyl-functionalised tripodal tris(urea) receptor (L) has been designed for sulphate binding. The neutral receptor formed the 1:1 binding mode with sulphate ion (as tetrabutylammonium salt). However, when L interacted with H ₂SO ₄, a 2:1 (host/guest) complex (HL) ₂SO ₄EtOH12.5H ₂O (1) was isolated. Crystal structural analysis showed that the tertiary amine N atom of L is protonated, and the sulphate ion is located outside the receptor rather than inside the tripodal cleft. ¹H NMR studies revealed that the 2:1 binding ratio was persistent in solution. Interestingly, the protonated receptor displayed an unusual enhanced binding for sulphate ion in aqueous environments because of the stronger electrostatic effect in the presence of water.

Original language	English
Pages (from-to)	88-94
Number of pages	7
Journal	Supramolecular Chemistry
Volume	24
Issue number	2
DOIs	https://doi.org/10.1080/10610278.2011.622389
Publication status	Published - 1 Feb 2012
Externally published	Yes

Keywords

protonation
quinolinyl
sulphate binding
tripodal tris-urea receptor

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10.1080/10610278.2011.622389

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title = "Sulphate binding by a quinolinyl-functionalised tripodal tris-urea receptor",

abstract = "A quinolinyl-functionalised tripodal tris(urea) receptor (L) has been designed for sulphate binding. The neutral receptor formed the 1:1 binding mode with sulphate ion (as tetrabutylammonium salt). However, when L interacted with H 2SO 4, a 2:1 (host/guest) complex (HL) 2SO 4EtOH12.5H 2O (1) was isolated. Crystal structural analysis showed that the tertiary amine N atom of L is protonated, and the sulphate ion is located outside the receptor rather than inside the tripodal cleft. 1H NMR studies revealed that the 2:1 binding ratio was persistent in solution. Interestingly, the protonated receptor displayed an unusual enhanced binding for sulphate ion in aqueous environments because of the stronger electrostatic effect in the presence of water.",

keywords = "protonation, quinolinyl, sulphate binding, tripodal tris-urea receptor",

author = "Yongjing Hao and Chuandong Jia and Shaoguang Li and Xiaojuan Huang and Yang, {Xiao Juan} and Christoph Janiak and Biao Wu",

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AU - Hao, Yongjing

AU - Jia, Chuandong

AU - Li, Shaoguang

AU - Huang, Xiaojuan

AU - Yang, Xiao Juan

AU - Janiak, Christoph

AU - Wu, Biao

PY - 2012/2/1

Y1 - 2012/2/1

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AB - A quinolinyl-functionalised tripodal tris(urea) receptor (L) has been designed for sulphate binding. The neutral receptor formed the 1:1 binding mode with sulphate ion (as tetrabutylammonium salt). However, when L interacted with H 2SO 4, a 2:1 (host/guest) complex (HL) 2SO 4EtOH12.5H 2O (1) was isolated. Crystal structural analysis showed that the tertiary amine N atom of L is protonated, and the sulphate ion is located outside the receptor rather than inside the tripodal cleft. 1H NMR studies revealed that the 2:1 binding ratio was persistent in solution. Interestingly, the protonated receptor displayed an unusual enhanced binding for sulphate ion in aqueous environments because of the stronger electrostatic effect in the presence of water.

KW - protonation

KW - quinolinyl

KW - sulphate binding

KW - tripodal tris-urea receptor

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Sulphate binding by a quinolinyl-functionalised tripodal tris-urea receptor

Abstract

Keywords

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