Yan Jijun, Kang Chuanqing, Bian Zheng, Ma Xiaoye, Jin Rizhe, Du Zhijun, Gao Lianxun
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, 130022, P. R. China.
University of Chinese Academy of Sciences, Beijing, 100049, P. R. China.
Chemistry. 2017 Apr 27;23(24):5824-5829. doi: 10.1002/chem.201700617. Epub 2017 Apr 10.
Recognition of enantiomers of chiral acids by anion-π or lone pair-π interactions has not yet been investigated but is a significant and attractive challenge. This study reports an optically active polymer-based supramolecular system with capabilities of discriminating enantiomers of various chiral acids. The polymer featuring alternate π-acidic naphthalenediimides (NDIs) and methyl l-phenylalaninates in the backbone exhibits an unprecedented slow self-assembly process that is susceptible to perturbation by various chiral acids. Thus, the combination of anion-π or lone pair-π interactions and sensitivity of the polymeric self-assembly process to external chiral species endows the system with recognition capabilities. This is the first time that anion-π or lone pair-π interactions have been applied in the recognition of enantiomers of various chiral acids with a single system. The results shed light on new strategies for material design by integrating π-acidic aromatic systems and chiral building blocks to afford relevant advanced functions.
通过阴离子-π或孤对-π相互作用识别手性酸对映体的研究尚未开展，但这是一项重大且具有吸引力的挑战。本研究报道了一种基于光学活性聚合物的超分子体系，它能够区分各种手性酸的对映体。该聚合物主链中交替排列着π-酸性萘二酰亚胺（NDIs）和L-苯丙氨酸甲酯，呈现出前所未有的缓慢自组装过程，该过程易受各种手性酸的干扰。因此，阴离子-π或孤对-π相互作用与聚合物自组装过程对外部手性物种的敏感性相结合，赋予了该体系识别能力。这是首次将阴离子-π或孤对-π相互作用应用于单一体系中识别各种手性酸的对映体。这些结果为通过整合π-酸性芳香体系和手性结构单元来提供相关先进功能的材料设计新策略提供了思路。
