The chemistry of Reissert compounds has been utilized to synthesize an activated difluorotetraketone monomer, 1 A-bis { 1-[ 4-(p-fluorobenzoyl)isoquinoly ] carbonyl } benzene (18). Two synthetic routes were explored in an attempt to find an efficient means of preparation. These routes entail preparation via a dibenzylic bis(isoquinoline) and a diketone bis(isoquinoline) system. These compounds were converted to their corresponding Reissert compounds. Reaction of the anion of the dibenzylic Reissert compound with p-fluorobenzaldehyde, followed by oxidation of both benzylic sites has produced the novel difluorotetraketone monomer. In addition, rearrangement of the dike tone Reissert compound has produced the novel difluorotetraketone monomer. This monomer offers a route to a novel family of poly(heteroarylene ethers). / Master of Science