Issue 20, 2019

Emergent supramolecular assembly properties of a recognition-encoded oligoester


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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Article information

Article type
Edge Article
04 Apr 2019
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
Creative Commons BY license

Chem. Sci., 2019,10, 5397-5404

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

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