H-Bonded Duplexes based on a Phenylacetylene Backbone

Change log
Swain, Jonathan 
Hunter, CA 

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.

0303 Macromolecular and Materials Chemistry
Journal Title
Journal of the American Chemical Society
Conference Name
Journal ISSN
Volume Title
American Chemical Society (ACS)
European Research Council (320539)
EPSRC (EP/J008044/4)
Engineering and Physical Sciences Research Council (EP/J008044/2), European Research Council (ERC-2012-AdG 320539-duplex)