A Molecular Communication Channel Consisting of a Single Reversible Chain of Hydrogen Bonds in a Conformationally Flexible Oligomer

Overview

Journal Chem

Publisher Elsevier

Date 2021 Sep 23

PMID 34553103

Citations 11

Authors

David T J Morris

Steven M Wales

David P Tilly

Elliot H E Farrar

Matthew N Grayson

John W Ward

Jonathan Clayden

Affiliations

Soon will be listed here.

Abstract

Communication of information through the global switching of conformation in synthetic molecules has hitherto entailed the inversion of chirality. Here, we report a class of oligomer through which information may be communicated through a global reversal of polarity. Ethylene-bridged oligoureas are constitutionally symmetrical, conformationally flexible molecules organized by a single chain of hydrogen bonds running the full length of the oligomer. NMR reveals that this hydrogen-bonded chain may undergo a coherent reversal of directionality. The directional uniformity of the hydrogen-bond chain allows it to act as a channel for the spatial communication of information on a molecular scale. A binding site at the terminus of an oligomer detects local information about changes in pH or anion concentration and transmits that information-in the form of a directionality switch in the hydrogen-bond chain-to a remote polarity-sensitive fluorophore. This propagation of polarity-encoded information provides a new mechanism for molecular communication.

Citing Articles

Cooperative intra- and intermolecular hydrogen bonding in scaffolded squaramide arrays.

Martinez-Crespo L, Whitehead G, Vitorica-Yrezabal I, Webb S Chem Sci. 2024; .

PMID: 39345772 PMC: 11428187. DOI: 10.1039/d4sc04337e.

Dynamic and Persistent Cyclochirality in Hydrogen-Bonded Derivatives of Medium-Ring Triamines.

Morris D, Wales S, Echavarren J, Zabka M, Marsico G, Ward J J Am Chem Soc. 2023; 145(34):19030-19041.

PMID: 37594473 PMC: 10472504. DOI: 10.1021/jacs.3c06570.

Anion-Dependent Hydrogen-Bond Polarity Switching in Ethylene-bridged Urea Oligomers.

Tilly D, Morris D, Clayden J Chemistry. 2023; 29(62):e202302210.

PMID: 37589333 PMC: 10946793. DOI: 10.1002/chem.202302210.

Conformational preference in difluoroacetamide oligomers: probing the potential for foldamers with C-H⋯O hydrogen bonds.

Zabka M, Clayden J Org Biomol Chem. 2023; 21(29):5939-5943.

PMID: 37436098 PMC: 10369364. DOI: 10.1039/d3ob00811h.

Chemically Fueled Communication Along a Scaffolded Nanoscale Array of Squaramides.

Martinez-Crespo L, Vitorica-Yrezabal I, Whitehead G, Webb S Angew Chem Int Ed Engl. 2023; 62(38):e202307841.

PMID: 37429824 PMC: 10952809. DOI: 10.1002/anie.202307841.

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