The synthesis of biaryl and terphenyl dicarboxaldehydes using Suzuki coupling methodology and their macrocyclisation reactions with 1R, 2R-diaminocyclohexane yielding novel polyimine macrocycles derived from the [2+ 2] and [3+ 3] cyclocondensation reactions is presented. The ratio of products was found to depend on the overall geometry of the dicarboxaldehydes.