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Abstract
New receptors based upon a carboxamidonaphthyridine unit derivatized with the polyaromatic segments [4-(1-pyrenyl)butyroylamino] and [3-(9-anthracenyl)propanoylamino] have been synthesized and studied by 1H NMR titration in their binding interaction to the guanosine-C8 adducts from the carcinogens 2-acetylaminofluorene and 2-aminofluorene. The high binding energy, in comparison with that of the non-derivatized analogues, is rationalized in terms of a bi-site interaction (hydrogen bonding and aromatic stacking). Although many factors may contribute to the strength of the host-guest complexes described herein, it appears that in some cases π-π interaction may induce a concomitant bending in the hydrogen bond system.