Abstract
The Lewis acidic redox-active and photoactive ruthenium(II) bipyridyl moiety in combination with amide (CO−NH) groups has been incorporated into acyclic, macrocyclic, and lower rim calix[4]arene structural frameworks to produce a new class of anion receptor with the dual capability of sensing anionic guest species via electrochemical and optical methodologies. Single-crystal X-ray structures of (1)Cl and (11)H2PO4 reveal the importance of hydrogen bonding to the overall anion complexation process. In the former complex, six hydrogen bonds (two amide and four C−H groups) stabilize the Cl- anion and three hydrogen bonds (two amide and one calix[4]arene hydroxyl) effect H2PO4- complexation with 11. Proton NMR titration investigations in deuterated DMSO solutions reveal these receptors form strong and, in the case of the macrocyclic 5 and calix[4]arene-containing receptor 11, highly selective complexes with H2PO4-. Cyclic and square-wave voltammetric studies have demonstrated these receptors to electrochemica...
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