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Issue 1, 2015
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Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing π-extended diarylacetylene motifs

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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.

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

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Publication details

The article was received on 30 Sep 2014, accepted on 30 Oct 2014 and first published on 10 Nov 2014


Article type: Communication
DOI: 10.1039/C4OB02081B
Citation: Org. Biomol. Chem., 2015,13, 68-72
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    Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing π-extended diarylacetylene motifs

    S. De Ornellas, J. M. Slattery, R. M. Edkins, A. Beeby, C. G. Baumann and I. J. S. Fairlamb, Org. Biomol. Chem., 2015, 13, 68
    DOI: 10.1039/C4OB02081B

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