一种手性卤键[3]轮烷用于识别和检测生物相关二羧酸阴离子。
A Chiral Halogen-Bonding [3]Rotaxane for the Recognition and Sensing of Biologically Relevant Dicarboxylate Anions.
机构信息
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
Department of Chemistry, CICECO-Aveiro Institute of Materials and Department of Medical Sciences, iBiMED-Institute of Biomedicine, University of Aveiro, 3810-193, Aveiro, Portugal.
出版信息
Angew Chem Int Ed Engl. 2018 Jan 8;57(2):584-588. doi: 10.1002/anie.201711176. Epub 2017 Dec 8.
The unprecedented application of a chiral halogen-bonding [3]rotaxane host system for the discrimination of stereo- and E/Z geometric isomers of a dicarboxylate anion guest is described. Synthesised by a chloride anion templation strategy, the [3]rotaxane host recognises dicarboxylates through the formation of 1:1 stoichiometric sandwich complexes. This process was analysed by molecular dynamics simulations, which revealed the critical synergy of halogen and hydrogen bonding interactions in anion discrimination. In addition, the centrally located chiral (S)-BINOL motif of the [3]rotaxane axle component facilitates the complexed dicarboxylate species to be sensed via a fluorescence response.
描述了手性卤键[3]轮烷主体系统在识别羧酸根阴离子客体的立体和 E/Z 几何异构体方面的前所未有的应用。通过氯离子模板策略合成的[3]轮烷主体通过形成 1:1 化学计量的夹心配合物来识别羧酸根。这一过程通过分子动力学模拟进行了分析，该模拟揭示了卤键和氢键相互作用在阴离子识别中的关键协同作用。此外，[3]轮烷轴组件中位于中心的手性(S)-BINOL 模体有助于通过荧光响应来感应被配合的羧酸根物种。
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