Anion Recognition and Cation-Induced Molecular Motion in a Heteroditopic [2]Rotaxane

被引:23
作者
Leontiev, Alexandre V. [1 ]
Jemmett, Charlotte A. [1 ]
Beer, Paul D. [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
基金
英国工程与自然科学研究理事会;
关键词
anions; molecular motion; receptors; rotaxanes; template synthesis; INDUCED TRANSLATIONAL ISOMERISM; ION-PAIR RECOGNITION; ROTAXANE; CATENANE; TEMPLATE; PSEUDOROTAXANES; PORPHYRINS; RECEPTORS; STRENGTH; MOTORS;
D O I
10.1002/chem.201002405
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A heteroditopic [2]rotaxane consisting of a calix[4]diquinone-isophthalamide macrocycle and 3,5-bisamide pyridinium axle components with the capability of switching between two positional isomers in response to barium cation recognition is synthesised. The anion binding properties of the rotaxane's interlocked cavity together with Na+, K+, NH4+ and Ba2+ cation recognition capabilities are elucidated by H-1 NMR and UV-visible spectroscopic titration experiments. Upon binding of Ba2+, molecular displacement of the axle's positively charged pyridinium group from the rotaxane's macrocyclic cavity occurs, whereas the monovalent cations Na+, K+ and NH4+ are bound without causing significant co-conformational change. The barium cation induced shuttling motion can be reversed on addition of tetrabutylammonium sulfate.
引用
收藏
页码:816 / 825
页数:10
相关论文
共 70 条
[1]   Bipyrrole-based [2]catenane:: A new type of anion receptor [J].
Andrievsky, A ;
Ahuis, F ;
Sessler, JL ;
Vögtle, F ;
Gudat, D ;
Moini, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) :9712-9713
[2]  
[Anonymous], 2007, ANGEW CHE
[3]  
[Anonymous], 2005, ANGEW CHEM INT EDIT
[4]  
Asakawa M, 1999, EUR J ORG CHEM, V1999, P985, DOI 10.1002/(SICI)1099-0690(199905)1999:5<985::AID-EJOC985>3.0.CO
[5]  
2-O
[6]   Light powered molecular machines [J].
Balzani, Vincenzo ;
Credi, Alberto ;
Venturi, Margherita .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (06) :1542-1550
[7]   An Ion-Pair Template for Rotaxane Formation and its Exploitation in an Orthogonal Interaction Anion-Switchahle Molecular Shuttle [J].
Barrell, Michael J. ;
Leigh, David A. ;
Lusby, Paul J. ;
Slawin, Alexandra M. Z. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) :8036-8039
[8]  
BARRELL MJ, 2008, ANGEW CHEM, V120, P8156
[9]   Synthesis of a polypseudorotaxane, polyrotaxane, and polycatenane using 'click' chemistry [J].
Bria, Marc ;
Bigot, Julien ;
Cooke, Graeme ;
Lyskawa, Joel ;
Rabani, Gouher ;
Rotello, Vincent M. ;
Woisel, Patrice .
TETRAHEDRON, 2009, 65 (01) :400-407
[10]   Interlocked Host Anion Recognition by an Indolocarbazole-Containing [2]Rotaxane [J].
Brown, Asha ;
Mullen, Kathleen M. ;
Ryu, Jay ;
Chmielewski, Michal J. ;
Santos, Sergio M. ;
Felix, Vitor ;
Thompson, Amber L. ;
Warren, John E. ;
Pascu, Sofia I. ;
Beer, Paul D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) :4937-4952