2,5‐Diphenyl‐3,4‐bis(2‐pyridyl)cyclopenta‐2,4‐dien‐1‐one as a Redox‐Active Chelating Ligand

Abstract

2,5-Diphenyl-3,4-bis(2-pyridyl)cyclopenta-2,4-dien-1-one (1), a close relative of tetraphenylcyclopentadienone, is a new ligand platform for use in redox switches and sensors. Compound 1 acts as a molecular electrochemical sensor towards a range of divalent metal ions and exhibits favourable two-wave behaviour. It forms chelates of the type [(1)MX2], whose stability is enhanced by five orders of magnitude upon one-electron reduction. The bite angle of 1 is close to 90 degrees in these complexes. The attachment of the 14-valence-electron Cp*Co fragment to the cyclopentadienone pi system reduces the bite angle and thus modulates the binding characteristics of 1.