Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA UK.
Chemistry. 2010 Nov 22;16(44):13082-94. doi: 10.1002/chem.201002076.
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. (1)H 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 enhanced and tuned through the attachment of electron-withdrawing substituents and by increasing its positive charge. A dicationic rotaxane selectively binds chloride in 35% water, wherein 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.
一种新的、多功能的氯离子模板合成途径被用于制备一系列八个新的[2]轮烷主体分子，包括第一个磺酰胺互锁体系。（1）H NMR 光谱滴定研究表明，轮烷能够在竞争的水溶剂介质中选择性地识别氯离子。通过引入吸电子取代基和增加正电荷，可进一步增强和调节互锁主体的卤化物结合亲和力。一个二价轮烷在 35%的水中选择性地结合氯离子，其中没有观察到氧阴离子结合的证据。NMR 光谱、X 射线结构分析和计算分子动力学模拟用于解释轮烷形成产率、阴离子结合强度和选择性趋势。
