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Emergent Supramolecular Assembly Properties of Recognition-Encoded Oligoesters

submitted on 02.03.2019, 16:01 and posted on 04.03.2019, 19:40 by Filip Szczypiński, Luca Gabrielli, Christopher Hunter
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 leads 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.


ERC-2012-AdG 320539-DUPLEX

H2020-MSCA-IF-2016 745730


Email Address of Submitting Author


University of Cambridge


United Kingdom

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest.

Version Notes

Added further funding acknowledgement.