Triazolylpyrenes: synthesis, fluorescence properties, and incorporation into DNA

Synthesis of 1,6- and 1,8-triazolylpyrenes and their incorporation into oligonucleotides is described. In hybrids, triazolylpyrenes adopt interstrand stacking interactions. Exciton coupling is observed for the duplex containing a pair of the 1,6-isomer indicating a well-defined helical arrangement o...

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Veröffentlicht in:	Organic letters 2008-05, Vol.10 (10), p.2011-2014
Hauptverfasser:	Werder, Sarah, Malinovskii, Vladimir L, Häner, Robert
Format:	Artikel
Sprache:	eng
Schlagworte:	DNA - chemistry Fluorescence Intercalating Agents - chemical synthesis Intercalating Agents - chemistry Molecular Structure Pyrenes - chemical synthesis Pyrenes - chemistry Temperature Triazoles - chemical synthesis Triazoles - chemistry
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Beschreibung
Zusammenfassung:	Synthesis of 1,6- and 1,8-triazolylpyrenes and their incorporation into oligonucleotides is described. In hybrids, triazolylpyrenes adopt interstrand stacking interactions. Exciton coupling is observed for the duplex containing a pair of the 1,6-isomer indicating a well-defined helical arrangement of the triazolylpyrene building blocks. Triazole substitution results in pronounced red-shifts of monomer as well as excimer fluorescence. Furthermore, quantum yields of the formed excimers are remarkably high.
ISSN:	1523-7060
DOI:	10.1021/ol8006474