Design of polyaromatic ethers using cyclopentadienyliron complexes

Nucleophilic aromatic substitution of cyclopentadienyliron complexes of chloroarenes with oxygen-containing nucleophiles led to the isolation of a number of aromatic ether complexes (2, 5a-e) in very good yields. Reactions of these complexes with l-naphthol, followed by removal of the cyclopentadienyliron moieties produced aromatic ether compounds with terminal naphthoxy groups (3, 7a-e). Polymerization of these monomers in the presence of ferric chloride gave the poly(aryl ethers) 4 and 8a-e. These materials were obtained with weight-average molecular weights up to 139 900 g/mol. Thermogravimetric analysis of the poly(aryl ethers) showed that these materials displayed no significant weight loss until 458-575 degrees C. The glass transition temperatures for these polymers ranged from 147 to 226 degrees C, as measured by differential scanning calorimetry.