Issue 2, 2020

Two-component assembly of recognition-encoded oligomers that form stable H-bonded duplexes

Abstract

A new family of recognition-encoded oligomers that form stable duplexes in chloroform have been prepared. Monomer building blocks composed of dialdehydes functionalised with either a trifluoromethylphenol or phosphine oxide H-bond recognition unit were prepared. The dialdehydes were coupled with diamines by imine formation and then reduction to give homo-oligomers between one and three recognition units in length. Duplex formation was characterised by 19F and 1H NMR titration experiments in toluene and in chloroform. For duplexes formed between length complementary H-bond donor and acceptor homo-oligomers, an order of magnitude increase in stability was observed for every base-pair added to the duplex in chloroform. The effective molarity for the intramolecular H-bonds responsible for zipping up the duplex is 30 mM, which results in the fully assembled duplex in all cases. The uniform increase in duplex stability with oligomer length suggests that the backbone structure and geometry is likely to be compatible with the formation of extended duplexes in longer oligomers.

Graphical abstract: Two-component assembly of recognition-encoded oligomers that form stable H-bonded duplexes

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Aug 2019
Accepted
19 Nov 2019
First published
29 Nov 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., 2020,11, 561-566

Two-component assembly of recognition-encoded oligomers that form stable H-bonded duplexes

L. Gabrielli, D. Núñez-Villanueva and C. A. Hunter, Chem. Sci., 2020, 11, 561 DOI: 10.1039/C9SC04250D

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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