Synthesis of self-crosslinking poly(p-phenylene)s
Several functionalized rigid rod polyparaphenylenes that can undergo self-crosslinking via nucleophilic aromatic substitution were synthesized from 4′-methoxy-DBP (DBP = 2,5-dichlorobenzophenone) (1), 4′-aceto-DBP (2), 2,5-dichlorophenol acetate (3) and 4′-fluoro-DBP (4). Copolymers of 2 with 4 and 3 with 4 can be crosslinked in solution or as a film. Homopolymers of 2 gave only oligomers. However, a 50:50 copolymerization of 3 and 4 gave higher molecular weight with a glass transition of 196 °C. All ester functionality in the copolymers was completely hydrolyzed to the corresponding phenol during work-up. Self-crosslinking was carried out in basic N,N-dimethylformamide to give insoluble materials with good thermal stabilities.
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