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

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JournalOrganic and Biomolecular Chemistry
DateE-pub ahead of print - 10 Nov 2014
DatePublished (current) - 7 Jan 2015
Issue number1
Volume13
Number of pages5
Pages (from-to)68-72
Early online date10/11/14
Original languageEnglish

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

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