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Issue 20, 2019
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Emergent supramolecular assembly properties of a recognition-encoded oligoester

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Abstract

The sequences of oligomeric molecules equipped with interacting side-chains encode the three-dimensional structure, the supramolecular assembly properties, and ultimately function. In an attempt to replicate the duplex forming properties of nucleic acids, an oligoester containing an alternating sequence of hydrogen bonding donor (D) and acceptor (A) residues was synthesised. Characterisation of assembly properties of the ADAD oligomer revealed a supramolecular architecture that resembles the kissing stem-loops motif found in folded RNA. NMR dilution and melting experiments in chloroform and 1,1,2,2-tetrachloroethane show that intramolecular hydrogen bonding interactions between the terminal phenol and phosphine oxide recognition sites in the ADAD 4-mer lead to 1,4-folding. This folded stem-loop structure can be denatured to give the single strand by heating. At higher concentrations or lower temperatures, the stem-loop dimerises via intermolecular hydrogen bonding interactions between the two inner recognition sites, leading to a kissing stem-loops structure. The results suggest a rich supramolecular chemistry for these recognition-encoded oligoesters and lay strong foundations for the future development of new functional materials based on synthetic information molecules.

Graphical abstract: Emergent supramolecular assembly properties of a recognition-encoded oligoester

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Supplementary files

Article information


Submitted
04 Apr 2019
Accepted
25 Apr 2019
First published
02 May 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 5397-5404
Article type
Edge Article

Emergent supramolecular assembly properties of a recognition-encoded oligoester

F. T. Szczypiński, L. Gabrielli and C. A. Hunter, Chem. Sci., 2019, 10, 5397 DOI: 10.1039/C9SC01669D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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