Département de chimie moléculaire

Novel synthetic approaches toward redox active calixarene-based receptors are described wherein ferrocene fragments have been introduced at the lower rim through anion-binding urea or amide connections. A thorough 1H NMR investigation on macrocycles was performed in order to est. their hydrogen bonding-driven self-assocn. properties and improve our understanding of the correlation between mol. structures and redox properties. The anion-binding properties of these artificial receptors have also been revealed by NMR spectroscopy and thoroughly investigated by electrochem. methods. We esp. assessed the importance of the urea-phosphate bonds in the obsd. electrochem. response upon studying receptors wherein the ferrocene reporters and binding fragments are intimately assocd. or fully disconnected through a long alkyl chain. The exptl. results clearly showed the utmost importance of ion pairing effects in the electrochem. recognition process accounting for most of the transduction signal in org. apolar media. [on SciFinder(R)]