Show simple item record

dc.contributor.authorSwain, Jonathan
dc.contributor.authorIadevaia, Giulia
dc.contributor.authorHunter, CA
dc.date.accessioned2018-11-14T00:30:34Z
dc.date.available2018-11-14T00:30:34Z
dc.date.issued2018-09-12
dc.identifier.issn1520-5126
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/285023
dc.description.abstractComplementary 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.
dc.description.sponsorshipEngineering and Physical Sciences Research Council (EP/J008044/2), European Research Council (ERC-2012-AdG 320539-duplex)
dc.publisherAmerican Chemical Society (ACS)
dc.rightsAttribution 4.0 International
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.titleH-Bonded Duplexes based on a Phenylacetylene Backbone
dc.typeArticle
prism.endingPage11536
prism.issueIdentifier36
prism.publicationNameJournal of the American Chemical Society
prism.startingPage11526
prism.volume140
dc.identifier.doi10.17863/CAM.32393
dcterms.dateAccepted2018-08-20
rioxxterms.versionofrecord10.1021/jacs.8b08087
rioxxterms.licenseref.urihttp://creativecommons.org/licenses/by/4.0/
rioxxterms.licenseref.startdate2018-08-20
dc.contributor.orcidIadevaia, Giulia [0000-0002-1182-0341]
dc.contributor.orcidHunter, Christopher [0000-0002-5182-1859]
dc.identifier.eissn1520-5126
rioxxterms.typeJournal Article/Review
pubs.funder-project-idEuropean Research Council (320539)
pubs.funder-project-idEPSRC (EP/J008044/4)
cam.issuedOnline2018-09-04


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record

Attribution 4.0 International
Except where otherwise noted, this item's licence is described as Attribution 4.0 International