Synthesis and Photophysical Characterisation of Fluorescent 8-(1H-1,2,3-Triazol-4-yl)adenosine Derivatives

A series of 8-(1H-1,2,3-triazol-4-yl)-substituted adenosine derivatives have been synthesised by using Sonogashira cross-coupling and click chemistry. The use of click chemistry enables an easy access to different substituents in the 4-position of the triazole ring. The modified nucleosides show high absorptivities due to a single strongly allowed electronic transition and, for some of the derivatives, high quantum yields in organic as well as in water solution making them promising as fluorescent probes in nucleic acid contexts. Furthermore, the different substituents of the 1,2,3-triazole makes the wavelength of emission tunable without changing the absorption properties substantially. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)