Many bioenergetic processes require the coupled transfer of multiple electrons and protons. We investigate diarylamine synthetic models that are able to transfer 2H+ and 2e-. A Buchwald-Hartwig cross-coupling strategy affords a new series of diarylamines varying Hammett substituent parameters and the electronic coupling between the redox centers. Electrochemical studies in the presence of bases of different strengths allow us to investigate the dependence on substituent parameters, electronic coupling, and base strength of the extent and onset of redox potential inversion.

Synthesis & electrochemical studies of diarylamines

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