Enantioselective recognition in water remains an ongoing challenge in supramolecular chemistry but is routine in nature. Herein, we report the first enantiopure pair of biomimetic macrocyclic receptors with hydrogen bonding donors in their deep hydrophobic cavities. The chiral naphthotubes can be efficiently synthesized through a chirality-directed macrocyclization strategy and are able to discriminate the enantiomers of neutral chiral molecules in water. Density functional theory calculations reveal that the “three-point contact” model effectively explains their enantioselectivity. The differential noncovalent interactions inside the hydrophobic cavity are responsible for the enantioselective recognition. Moreover, these chiral naphthotubes are both fluorescent and circular dichroism (CD)-active. In CD spectroscopy, they have been demonstrated to have the ability to detect nonchromophoric, achiral molecules in water. And, the use of fluorescence spectroscopy has aided in the determination of the enantiomeric excess (ee) values of chiral molecules. The results and conclusions obtained with these chiral biomimetic receptors can be used to better understand enantioselective recognition in biological systems.

中文翻译：

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一对手性仿生大环受体对水中的中性分子的对映选择性识别。

水中的对映选择性识别在超分子化学中仍然是一个持续的挑战，但实际上是常规的。在这里，我们报告的第一个对映纯对的仿生大环受体对在其深疏水腔中具有氢键供体。手性萘管可以通过手性导向的大环化策略有效合成，并且能够区分水中的中性手性分子的对映异构体。密度泛函理论计算表明，“三点接触”模型有效地解释了其对映选择性。疏水腔内部的差异性非共价相互作用负责对映选择性识别。此外，这些手性萘管具有荧光和圆二色性（CD）活性。在CD光谱学中，已证明它们具有检测水中非发色的非手性分子的能力。并且，荧光光谱法的使用有助于确定手性分子的对映体过量（ee）值。这些手性仿生受体获得的结果和结论可用于更好地理解生物系统中的对映选择性识别。