A Potent Halogen-Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis
A Potent Halogen-Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis
复制标题
DOI：
10.1002/anie.201907625
复制
发表时间：
2019-08-19
影响因子：
16.6
通讯作者：
Beer, Paul D.
中科院分区：
文献类型：
--
作者：
Bunchuay, Thanthapatra;Docker, Andrew;Beer, Paul D.
缺乏电子的全氟芳基取代基与双碘三唑吡啶基团的共价连接在水介质中产生了一个非常有效的卤素键供体基序，用于阴离子识别。这样的基序还建立了卤素键阴离子模板作为一种高效的方法，以前所未有的近定量产量构建机械互锁分子。所得到的含卤素键合[2]轮烷宿主物的双全氟芳基取代碘三唑吡啶轴在竞争性含50%水的水介质中表现出异常强的卤素键合亲和性，与氢键合轮烷宿主物类似物相比，其亲和性至少高出三个数量级。这些观察结果进一步支持和推进了卤素键作为识别水性介质阴离子的有力工具。
The covalent attachment of electron deficient perfluoroaryl substituents to a bis-iodotriazole pyridinium group produces a remarkably potent halogen bonding donor motif for anion recognition in aqueous media. Such a motif also establishes halogen bonding anion templation as a highly efficient method for constructing a mechanically interlocked molecule in unprecedented near quantitative yield. The resulting bis-perfluoroaryl substituted iodotriazole pyridinium axle containing halogen bonding [2]rotaxane host exhibits exceptionally strong halide binding affinities in competitive 50 % water containing aqueous media, by a factor of at least three orders of magnitude greater in comparison to a hydrogen bonding rotaxane host analogue. These observations further champion and advance halogen bonding as a powerful tool for recognizing anions in aqueous media.