H-Bonded Duplexes based on a Phenylacetylene Backbone
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Publication Date
2018-09-12Journal Title
Journal of the American Chemical Society
ISSN
1520-5126
Publisher
American Chemical Society (ACS)
Volume
140
Issue
36
Pages
11526-11536
Type
Article
Metadata
Show full item recordCitation
Swain, J., Iadevaia, G., & Hunter, C. (2018). H-Bonded Duplexes based on a Phenylacetylene Backbone. Journal of the American Chemical Society, 140 (36), 11526-11536. https://doi.org/10.1021/jacs.8b08087
Abstract
Complementary phenylacetylene oligomers equipped with phenol and phosphine oxide recognition sites form stable multiply H-bonded duplexes in toluene solution. Oligomers were prepared by Sonogashira coupling of diiodobenzene and bis-acetylene building blocks in the presence of mono-acetylene chain terminators. The product mixtures were separated by reverse phase preparative high-pressure liquid chromatography to give a series of pure oligomers up to seven recognition units in length. Duplex formation between length complemen-tary homo-oligomers was demonstrated by 31P NMR denaturation experiments using dimethyl sulfoxide as a competing H-bond accep-tor. The denaturation experiments were used to determine the association constants for duplex formation, which increase by nearly two orders of magnitude for every phenol-phosphine oxide base-pair added. These experiments show that the phenylacetylene backbone supports formation of extended duplexes with multiple cooperative intermolecular H-bonding interactions, and together with previous studies on the mixed sequence phenylacetylene 2-mer, suggest that this supramolecular architecture is a promising candidate for the de-velopment of synthetic information molecules that parallel the properties of nucleic acids.
Sponsorship
Engineering and Physical Sciences Research Council (EP/J008044/2), European Research Council (ERC-2012-AdG 320539-duplex)
Funder references
European Research Council (320539)
EPSRC (EP/J008044/4)
Identifiers
External DOI: https://doi.org/10.1021/jacs.8b08087
This record's URL: https://www.repository.cam.ac.uk/handle/1810/285023
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