Abstract
Ferrocenediyl systems offer a motif that incorporates multiple functionality and redox-active centers, enabling these units to be used as molecular scaffolds in linear and cyclic compounds. Herein, we discuss a new modular methodology for the synthesis and incorporation of ferrocenediyl motifs within extended conjugated systems. We have synthesized a family of compounds featuring ferrocenediyl-ethynyl units with various para-substituted aromatic linkages. Extended linear, open-chain species have been isolated and understanding towards the analogous cyclic compounds gained. The new compounds have been probed using NMR, mass spectrometry, cyclic voltammetry and X-ray crystallography to gain further understanding of their structural and electronic properties.
Highlights
The stability and redox activity of ferrocene has made it an attractive structural component and lead to the incorporation of the motif into many organometallic structures
Each bridged diferrocenediyl species was synthesized through a Sonogashira of 1,10 -diiodoferrocene with the arene units terminated ethynylwith ligands utilizing the coupling of 1,1′-diiodoferrocene with linking the arene linking units with terminated ethynyl ligands t widely
The unfortunate lack of cyclisation reactions under these conditions could be due to a high energy cyclisation barrier, steric strain and/or the conformation of the starting ferrocenediyl unit making cyclisation reaction difficult
Summary
The stability and redox activity of ferrocene has made it an attractive structural component and lead to the incorporation of the motif into many organometallic structures. There has been a drive to incorporate ferrocene motifs within macrocyclic structures. These systems offer the potential to study interference effects, redox behavior and conductance. Cyclic structures have been developed that contain closely bound ferrocene units and those which are separated by linker groups. Within these systems, phenyl linker groups have been used with both the ortho and meta substitution patterns but a para derivative has not yet been reported [11,12,13].
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