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Adaptive Chirality of an Achiral Cage: Chirality Transfer, Induction, and Circularly Polarized Luminescence through Aqueous Host–Guest Complexation
CCS Chemistry ( IF 9.4 ) Pub Date : 2020-12-24 , DOI: 10.31635/ccschem.020.202000509
Lin Cheng 1 , Kai Liu 2 , Yanjuan Duan 1 , Honghong Duan 1 , Yawen Li 1 , Meng Gao 3, 4, 5 , Liping Cao 1, 3, 4
Affiliation  

Chirality transfer, induction, and circularly polarized luminescence (CPL) using supramolecular hosts, such as macrocycles and cages, have been explored for wide-ranging applications in chiral recognition, sensing, catalysis, and chiroptical functional materials. Herein, we report the adaptive chirality of an achiral tetraphenylethene (TPE)-based octacationic cage ( 1) induced by binding with enantiopure deoxynucleotides ( A, T, C, and G) through host–guest (H–G) complexation in water. The hydrophobic cavity of the cage efficiently stabilizes the hydrogen-bonded dimerization of deoxynucleotides ( A2, T2, C2, and G2) to form H–G complexes in 1∶2 ratios. Given the photophysical properties and dynamic rotational conformation of the TPE units of the cage, cage⸧deoxynucleotide complexes exhibited excellent chiroptical properties based on chirality transfer and induction from the chiral guest to the achiral host. For this supramolecular system, the cage showed a unique adaptive chirality of the double clockwise-typed (PP) rotational conformation of the two TPE units, which was induced by chiral guests (e.g., A2, T2, C2, and G2) through H–G complexation in water. Furthermore, the adaptive chirality of the cage⸧deoxynucleotide complexes successfully induced CPL signals in homogeneous aqueous solutions. This study provides insights for the construction of adaptive chirality from an achiral TPE-based octacationic cage with dynamic conformational nature, and might facilitate further design of chiral functional materials for several applications, such as chiral recognition, sensing, displays, catalysis, and other chiral fluorescent supramolecular systems based on aqueous H–G complexation.



中文翻译:

非手性笼的适应性手性:手性转移,诱导和圆偏振发光通过主机和客体之间的水性复合。

已经探索了使用超分子宿主(例如大环化合物和笼子)的手性转移,诱导和圆极化发光(CPL),在手性识别,传感,催化和手性功能材料中具有广泛的应用。在此,我们报告了基于非手性四苯基乙烯(TPE)的八阳离子笼的适应性手性( 1个)与对映体纯脱氧核苷酸( 一种 Ť C G)通过水中的主客体(H–G)络合。笼子的疏水腔有效地稳定了脱氧核苷酸的氢键二聚化( A 2 Ť 2 C 2 G 2)以1∶2的比例形成H–G络合物。考虑到笼中TPE单元的光物理性质和动态旋转构象,基于手性传递和从手性客体向非手性宿主的诱导,笼型脱氧核苷酸复合物表现出优异的手性。对于此超分子系统,笼子显示了两个TPE单元的双顺时针型(PP)旋转构象的独特适应性手性,这是由手性客人(例如, A 2 Ť 2 C 2 G 2)通过水中的H–G络合。此外,笼式脱氧核苷酸复合物的适应性手性在均相水溶液中成功诱导了CPL信号。这项研究提供了从具有动态构象性质的基于非手性TPE的八官能笼构建适应性手性的见解,并可能有助于进一步设计用于多种应用的手性功能材料,例如手性识别,传感,展示,催化和其他手性基于水-H络合的荧光超分子系统。

更新日期:2020-12-25
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