Polymers containing polynuclear aromatics linked by one-carbon bridges

The conversion of naphthalene, anthracene, and phenanthrene to polymeric material via Friedel-Crafts chemistry was investigated. Synthesis of the polymers was accomplished by: (1) self-condensation of the chloromethylated aromatic substrate in the presence of AlCl₃ or SnCl₄ or (2) treatment with chloromethyl ethyl ether (CMEE) and SnCl₄, producing the chloromethylated substrate in situ, followed by self-condensation polymerization. Soluble or insoluble polymers were preferentially produced by varying the stoichiometry, time, or temperature of the reaction. The resulting polymers consisted of the polycyclic aromatic nuclei bridged by methylene groups. The regiochemistry of the polymer linkages was determined through the use of IR, ¹H- and ¹³C-NMR. The polymers showed relatively high thermal and thermo-oxidative stabilities (380–495°C). © 1992 John Wiley & Sons, Inc.