Poly(dibenzodiazocine)s, members of a new class of polyimines with high thermal stability and solubility in organic solvents, were synthesized from 2-amino-4'-fluorobenzophenone and three bisphenols. The high molecular weight polymers were shown by MALDI-TOF mass spectra to be accompanied by low molecular weight linear oligomers with the expected end group combinations and low molecular weight cyclic oligomers. The yields of the smaller cyclics were raised using a pseudo-dilution polymerization method.