It has been shown that it is possible to significantly perturb hydrogen bonding between organic molecules using oxidation or reduction. This study focuses on supramolecular complexes based on bis-dimethylaminophenylurea and a 2-methoxyethyl derivative of that urea which is more soluble in methylene chloride. In cyclic voltammetry (CV), these �hosts� (electroactive species) undergo two reversible oxidations which shift negative in potential with the addition of a cyclic diamide �guest� (non-electroactive species) indicating stronger hydrogen bonding to the oxidized form. Using the negative shift, we estimate that the binding constants increase by more than 1x105 upon oxidation. Currently CV simulations and NMR titrations are being performed to better understand this system.

Very strong redox-dependent hydrogen bonding between bis-dialkylaminophenylureas and a cyclic diamide

243rd National Meeting (2012)

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