A molecular communication channel consisting of a single reversible chain of hydrogen bonds in a conformationally flexible oligomer

David T.j. Morris, Steven M. Wales, David P. Tilly, Elliot H.e. Farrar, Matthew N. Grayson, John W. Ward, Jonathan Clayden

Research output: Contribution to journalArticlepeer-review

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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.
Original languageEnglish
Pages (from-to)2460-2472
JournalChem
Early online date28 Jul 2021
DOIs
Publication statusPublished - 9 Sept 2021

Bibliographical note

We acknowledge the support of the EPSRC through the Bristol Chemical Synthesis Centre for Doctoral Training (studentship to D.T.J.M.), Programme grant EP/P027067/1 (Molecular Robotics), and DTP funding (studentship to E.H.E.F.); the ERC through advanced grant 883786 (DOGMATRON); the Europen Commission through a Marie Sklodowska Curie fellowship to D.T.; the Leverhulme Trust; and Dr Hazel Sparkes for X-ray crystallographic analysis. This research made use of the Balena High Performance Computing (HPC) Service at the University of Bath.

Data and code availability
Crystallographic data for the structure reported in this article have been deposited at the Cambridge Crystallographic Data Centre, under deposition number CCDC: 1993164. Copies of the data can be obtained free of charge from https://www.ccdc.cam.ac.uk/structures/.

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