Unusually Strong Long-Distance Metal-Metal Coupling in Bis(ferrocene)-Containing BOPHY: An Introduction to Organometallic BOPHYs
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Updated: Apr 1, 2026

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
Hannah M Rhoda1, Kullapa Chanawanno2, Alexander J King1
1Department of Chemistry and Biochemistry, University of Minnesota - Duluth, 1039 University Drive, Duluth, MN 55812 (USA).
Abstract:
The first organometallic BOPHY (BOPHY=bis(difluoroboron)-1,2-bis{(pyrrol-2-yl)methylene}hydrazine) containing two ferrocene substituents was prepared through a Knoevenagel condensation between tetramethyl substituted BOPHY and ferrocene carboxaldehyde. An unprecedentedly strong long-range (≈17.2 Å) metal-metal coupling in this new complex was investigated using electrochemical, spectroelectrochemical, and chemical oxidation methods. Electrochemical data is indicative of a 200 mV separation between the first and the second ferrocene-centered oxidation processes. Formation of the mixed-valence states and appearance and disappearance of two NIR bands were observed during stepwise oxidation of the first organometallic BOPHY. The electronic structure and the nature of the excited states in this new chromophore were studied by DFT and TDDFT calculations.
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