Persistent Organic Nanopores Amenable to Structural and Functional Tuning

Journal of the American Chemical Society
Xiaoxi WeiBing Gong

Abstract

Rigid macrocycles 2, which share a hybrid backbone and the same set of side chains while having inner cavities with different inward-pointing functional groups, undergo similar nanotubular assembly as indicated by multiple techniques including (1)H NMR, fluorescence spectroscopy, and atomic force microscopy. The formation of tubular assemblies containing subnanometer pores is also attested by the different transmembrane ion-transport behavior observed for these macrocycles. Vesicle-based stopped-flow kinetic assay and single-channel electrophysiology with planar lipid bilayers show that the presence of an inward-pointing functional (X) group in the inner cavity of a macrocyclic building block exerts a major influence on the transmembrane ion-transporting preference of the corresponding self-assembling pore. Self-assembling pores with inward-pointing amino and methyl groups possess the surprising and remarkable capability of rejecting protons but are conducive to transporting larger ions. The inward-pointing groups also resulted in transmembrane pores with a different extent of positive electrostatic potentials, leading to channels having different preferences for transporting chloride ion. Results from this work demonstrate tha...Continue Reading

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Citations

Jul 20, 2016·Journal of the American Chemical Society·Sebastian BenzStefan Matile
Dec 10, 2016·Journal of the American Chemical Society·Tanmoy SahaPinaki Talukdar
Apr 6, 2017·Chemical Society Reviews·Philip A GaleRoberto Quesada
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May 6, 2017·Organic Letters·Ting HuBing Gong
Jun 22, 2018·Journal of the American Chemical Society·Changliang RenHuaqiang Zeng
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Jun 28, 2019·Journal of the American Chemical Society·Ethan N W Howe, Philip A Gale
Dec 23, 2017·Organic Letters·Thomas HjelmgaardSophie Faure

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