Abstract
Bisfunctional biphenylene monomers were designed, synthesized, and inspected as building blocks for aromatic polyketone synthesis. Starting from 2,2′-dimethoxybiphenylene ( 1), a highly activated acyl-acceptant biphenylene monomer affording high molecular weight polyketones, two types of biphenylene monomers were developed: 5,5′-bis(3[4]-chlorobenzoyl)-2,2′-dimethoxybiphenylenes ( 6) which readily gave the corresponding polyketones by nickel-catalyzed aromatic coupling polymerization and 2,2′-bis(trifluoromethyl)-4,4′-biphenylenedicarboxylic acid ( 27) which reacted with biphenylene 1 in P 2O 5CH 3SO 3H to give the corresponding fluorinated aromatic polyketone, selectively. The related model reactions for both monomer synthesis and polymerization were also investigated.
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