Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts

被引：22

作者：

Cornes, Stuart P. ^{[1
]}

Davies, Charles H. ^{[1
]}

Blyghton, David ^{[1
]}

Sambrook, Mark R. ^{[2
]}

Beer, Paul D. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Dstl Porton Down, Detect Dept, Salisbury SP4 0JQ, Wilts, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 09期

关键词：

SUPRAMOLECULAR CHEMISTRY; AQUEOUS-MEDIA; RECEPTORS; CATENANES; DONOR; ION;

D O I：

10.1039/c4ob02547d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rotaxane host system containing a novel halogen bonding (XB) 5-iodo-1,2,3-triazole functionalised pyridinium motif, within its axle component, has been prepared via a ring closing metathesis reaction, using chloride as a template. Proton NMR titration experiments, in competitive 1 : 1 CDCl3-CD3OD solvent media, showed the XB rotaxane selectively bound halides over larger, more basic oxoanions. An all hydrogen bonding proto-triazole containing rotaxane analogue was also prepared, which in stark contrast demonstrated a reversal in the anion selectivity trend, with a preference for dihydrogen phosphate over the halides which is unprecedented for an interlocked host system.

引用

页码：2582 / 2587

页数：6

共 31 条

[1] Halogen bonding in solution: thermodynamics and applications [J].

Beale, Thomas M. ;

Chudzinski, Michael G. ;

Sarwar, Mohammed G. ;

Taylor, Mark S. .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (04) :1667-1680

[2] Synthesis of 5-lodo-1,4-disubstituted-1,2,3-triazoles Mediated by in Situ Generated Copper(I) Catalyst and Electrophilic Triiodide Ion [J].

Brotherton, Wendy S. ;

Clark, Ronald J. ;

Zhu, Lei .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15) :6443-6455

[3] Interlocked host molecules for anion recognition and sensing [J].

Caballero, Antonio ;

Zapata, Fabiola ;

Beer, Paul D. .

COORDINATION CHEMISTRY REVIEWS, 2013, 257 (17-18) :2434-2455

[4] A Halogen-Bonding Catenane for Anion Recognition and Sensing [J].

Caballero, Antonio ;

Zapata, Fabiola ;

White, Nicholas G. ;

Costa, Paulo J. ;

Felix, Vitor ;

Beer, Paul D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (08) :1876-1880

[5] A Bidentate Halogen-Bonding Bromoimidazoliophane Receptor for Bromide Ion Recognition in Aqueous Media [J].

Caballero, Antonio ;

White, Nicholas G. ;

Beer, Paul D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (08) :1845-1848

[6] 2-Iodo-imidazolium receptor binds oxoanions via charge-assisted halogen bonding [J].

Cametti, Massimo ;

Raatikainen, Kari ;

Metrangolo, Pierangelo ;

Pilati, Tullio ;

Terraneo, Giancarlo ;

Resnati, Giuseppe .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (07) :1329-1333

[7] Anion Receptors Composed of Hydrogen- and Halogen-Bond Donor Groups: Modulating Selectivity With Combinations of Distinct Noncovalent Interacitons [J].

Chudzinski, Michael G. ;

McClary, Corey A. ;

Taylor, Mark S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10559-10567

[8] Measurements of weak halogen bond donor abilities with tridentate anion receptors [J].

Dimitrijevic, Elena ;

Kvak, Olga ;

Taylor, Mark S. .

CHEMICAL COMMUNICATIONS, 2010, 46 (47) :9025-9027

[9] Advances in Anion Supramolecular Chemistry: From Recognition to Chemical Applications [J].

Evans, Nicholas H. ;

Beer, Paul D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (44) :11716-11754

[10] Progress in the synthesis and exploitation of catenanes since the Millennium [J].

Evans, Nicholas H. ;

Beer, Paul D. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4658-4683

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