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Issue 3, 2016
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Mix and match backbones for the formation of H-bonded duplexes

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Abstract

The formation of well-defined supramolecular assemblies involves competition between intermolecular and intramolecular interactions, which is quantified by effective molarity. Formation of a duplex between two oligomers equipped with recognition sites displayed along a non-interacting backbone requires that once one intermolecular interaction has been formed, all subsequent interactions take place in an intramolecular sense. The efficiency of this process is governed by the geometric complementarity and conformational flexibility of the backbone linking the recognition sites. Here we report a series of phosphine oxide H-bond acceptor AA 2-mers and phenol H-bond donor DD 2-mers, where the two recognition sites are connected by isomeric backbone modules that vary in geometry and flexibility. All AA and DD combinations form stable AA·DD duplexes, where two cooperative H-bonds lead to an increase in stability of an order of magnitude compared with the corresponding A·D complexes that can only form one H-bond. For all six possible backbone combinations, the effective molarity for duplex formation is approximately constant (7–20 mM). Thus strict complementarity and high degrees of preorganisation are not required for efficient supramolecular assembly. Provided there is some flexibility, quite different backbone modules can be used interchangeably to construct stable H-bonded duplexes.

Graphical abstract: Mix and match backbones for the formation of H-bonded duplexes

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The article was received on 20 Nov 2015, accepted on 18 Dec 2015 and first published on 07 Jan 2016


Article type: Edge Article
DOI: 10.1039/C5SC04467G
Chem. Sci., 2016,7, 1760-1767
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Mix and match backbones for the formation of H-bonded duplexes

    G. Iadevaia, A. E. Stross, A. Neumann and C. A. Hunter, Chem. Sci., 2016, 7, 1760
    DOI: 10.1039/C5SC04467G

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