resumo
A new, versatile chloride anion templating synthetic pathway is exploited for the preparation of a series of eight new [2]rotaxane host molecules, including the first sulfonamide interlocked system H-1 NMR spectroscopic titration investigations demonstrate the rotaxanes' capability to selectively recognise the chloride anion in competitive aqueous solvent media The interlocked host's halide binding affinity can be further en hanced and tuned through the attachment of electron withdrawing substituents and by increasing its positive charge A dicationic rotaxane selectively binds chloride in 35% water, where in no evidence of oxoanion binding is observed NMR spectroscopy, X-ray structural analysis and computational molecular dynamics simulations are used to account for rotaxane formation yields, anion binding strengths and selectivity trends
palavras-chave
ANION RECEPTORS; PSEUDOPEPTIDIC MACROCYCLES; COORDINATION CHEMISTRY; TRANSITION-METAL; HYDROGEN-BONDS; RECOGNITION; COMPLEXES; BINDING; TEMPLATION; SENSORS
categoria
Chemistry
autores
Hancock, LM; Gilday, LC; Carvalho, S; Costa, PJ; Felix, V; Serpell, CJ; Kilah, NL; Beer, PD
nossos autores
Paulo Jorge Ferreira de Matos Costa
Bolseiro de pós-Doutoramento
Sílvia Cristina Ferreira de Carvalho
Bolseiro de pós-Doutoramento
Vítor Félix
Professor Associado com Agregaçãoagradecimentos
We thank the EPSRC for a studentship (L M) and Johnson Matthey for CASE studentship (C J S) N L K acknowledges the Royal Commission for the Exhibition of 1851 for a research fellowship P J C and S C thank FCT for the post doctoral grants SFRH/BPD/27082/2006 and SFRH/BPD/42357/2007 respectively VF acknowledges the FCT with co participation of the European Community fund FEDER for financial support under project PTDC/QUI/68582/2006 We also thank Diamond Light Source for an award of beam time on I19 (MT1880) the beamline instrument scientists for their assistance and Dr N H Rees for NMR advice