An alkyne-containing multiple aromatic ether-linked phthalonitrile has been synthesized and characterized. The oligomeric phthalonitrile monomer was prepared from the reaction of an excess amount of bisphenol A with 4,4-dibromotolane in the presence of K2CO3 in a N,N-dimethylformamide/toluene solvent mixture, followed by end-capping with 4-nitrophthalonitrile in a two-step, one-pot reaction. After being cured in the presence of bis(4-[4-aminophenoxy]phenyl)sulfone, the polymeric properties of the alkyne- and non-alkyne-containing oligomeric phthalonitrile resins were compared. Rheometric measurements and thermogravimetric analysis showed that the alkyne-containing oligomeric phthalonitrile resin had better mechanical properties than an analogous non-alkyne-containing resin cured under identical conditions and exhibited excellent thermal and oxidative properties. (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4774-4778