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

Sara De Ornellas, John M. Slattery, Robert M. Edkins, Andrew Beeby, Christoph G. Baumann, Ian J.S. Fairlamb

Research output: Contribution to journalArticle

6 Citations (Scopus)

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. This journal is

Original languageEnglish
Pages (from-to)68-72
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number1
DOIs
Publication statusPublished - 7 Jan 2015

Keywords

  • fluorescent 7-deazaadenosine nucleosides
  • cross-coupling approaches

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