Synthesis and Ring-Opening Metathesis Polymerization of Aryl-Substituted 1,1‘-(1,3-Butadienylene)ferrocenes
Citations Over TimeTop 12% of 2005 papers
Abstract
The unsaturated aryl-substituted ferrocenophanes 1,1‘-(1-phenylbuta-1,3-diene-1,4-diyl)ferrocene and 1,1‘-(1-mesitylbuta-1,3-diene-1,4-diyl)ferrocene were synthesized and used to prepare high molecular weight conjugated polymers by ring-opening metathesis polymerization. X-ray crystal structures of the phenyl- and mesityl-substituted monomers showed substantial bond angle strain in the butadiene bridge. The monomers were readily polymerized upon exposure to a tungsten-based initiator to give high molecular weight polymers that were soluble in common organic solvents. UV/vis spectral analysis indicated that the aryl moieties gave rise to enhanced conjugation when compared to related alkyl-substituted ferrocene-containing polymers. The enhanced conjugation was further supported by electrochemical analysis. The thermal stability of the new ferrocene-containing polymers was similar to that of oligomeric poly(ferrocenylene), and the conductivities upon doping were on the order of 10-5 S cm-1.