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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
2,5-Diphenyl-3,4-bis(2-pyridyl)cyclopenta-2,4-dien-1-one as a redox-active chelating ligand
Ulrich Siemeling1, Imke Scheppelmann, Jürgen Heinze
1Science Department and Center for Interdisciplinary, Nanostructure Science and Technology (CINSaT), University of Kassel, 34109 Kassel, Germany. siemeling@uni-kassel.de
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.
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