Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing pi-extended diarylacetylene motifs

De Ornellas, S.; Slattery, J.M.; Edkins, R.M.; Beeby, A.; Baumann, C.G.; Fairlam, I.J.S.

Abstract

C-modified 7-deazaadenosines containing a diphenylacetylene moiety have been synthesised using cross-coupling approaches. The C-modified nucleosides exhibit remarkable fluorescence properties, including high quantum yields. Solvatochromic studies show a near linear correlation between the Stokes shift and solvent polarity which is indicative of intramolecular charge transfer. DFT calculations have allowed us to correlate the experimentally observed photophysical properties with the calculated HOMO–LUMO energy gaps within a series of real and model compounds.

Citation

De Ornellas, S., Slattery, J., Edkins, R., Beeby, A., Baumann, C., & Fairlam, I. (2015). Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing pi-extended diarylacetylene motifs. Organic and Biomolecular Chemistry, 13(1), 68-72. https://doi.org/10.1039/c4ob02081b

• Journal Article Type: Article
• Acceptance Date: Oct 30, 2014
• Online Publication Date: Nov 10, 2014
• Publication Date: 2015-01
• Deposit Date: Apr 15, 2016
• Journal: Organic and Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 13
• Issue: 1
• Pages: 68-72
• DOI: https://doi.org/10.1039/c4ob02081b