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Amide naphthotubes:Biomimetic macrocycles for selective molecular recognition

Chinese Chemical Letters 2024年第4期35卷 124-131页

作者： Cheng-Da Zhao Huan Yao Shi-Yao Li Fangfang Du Li-Li Wang Liu-Pan Yang School of Pharmaceutical Science Postdoctoral Research Station of Basic MedicineHengyang Medical SchoolUniversity of South ChinaHengyang 421001China

Selective molecular recognition in water is routine for bioreceptors,but remains challenging for synthetic hosts.This is principally because noncovalent interactions are usually less efficient in aqueous environments.By mimicking the cavity feature of bioreceptors,Prof.Wei Jiang proposed and clarified the concept of“endo-functionalized cavity”.Through situating polar binding sites into a deep hydrophobic cavity,we designed and synthesized several macrocyclic hosts,among which amide naphthotubes are the most representative.The hosts can selectively recognize various polar molecules including organic micropollutants,drug molecules,and chiral molecules in water by employing the hydrophobic effect and shielded hydrogen bonding.In addition,these biomimetic hosts have been applied in spectroscopic analysis,adsorptive separation and self-assembly.In this review,we provide an overview of recent advances on amide naphthotubes with special emphasis on the efforts of Jiang's group.We are convinced that these biomimetic macrocycles will make further contributions to supramolecular chemistry and beyond.

关键词： Molecular recognition Supramolecular chemistry Amide naphthotube endo-functionalized cavity Biomimetic macrocycle

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Selective recognition of methyl viologen by an endo-functionalized naphthobox

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Chinese Chemical Letters 2022年第11期33卷 4896-4899页

作者： Weier Liu Linghui Kong Mao Quan Huan Yao Liupan Yang Ho Yu Au-Yeung Wei Jiang Guangdong Provincial Key Laboratory of Catalysis and Department of Chemistry Shenzhen Grubbs InstituteSouthern University of Science and TechnologyShenzhen 518055China Department of Chemistry The University of Hong KongHong KongChina

Highly selective binding of structurally similar substrates is common for biomolecular recognition,but is often challenging to realize in synthetic hosts.Herein,we report highly selective binding of methyl viologen over other analogues by an endo-functionalized naphthobox.X-ray single crystal structure and Density Functional Theory(DFT)calculations revealed that the endo-functionalized groups in the cavity of the naphthobox is important for the high binding selectivity through the formation of multiple C-H…N,C-H…π,andπ…πinteractions with methyl viologen.

关键词： Molecular recognition Host-guest chemistry endo-functionalized cavity Hydrogen bond Naphthobox

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