Synthesis of Macrocyclic Aryl Ethers Containing the Tetraphenylbenzene Moiety

Cyclic aryl ether ketone oligomers containing the 1,2-dibenzoyl-3,4,5,6-tetraphenylbenzene moiety were synthesized in high yield by reaction of 1,2-bis(4-fluorobenzoyl)-3,4,5,6-tetraphenylbenzene with bisphenols in DMF in the presence of potassium carbonate. The diketone monomer has low solubility in DMF, and high dilution conditions were obtained by adding the solid reactants in portions during the course of the reaction. The cyclic ether ketone oligomers were also transformed into cyclic ether phthalazines by reaction with hydrazine. The cyclics formed are crystalline and have lower T g s than their amorphous linear counterparts.