A series of polymeric chalcones based on 1,4-diacetylbenzene (1,4-DAB) and iso- and terephthaldehydes (iPhal and tPhal, respectively) were synthesized using both base and acid catalysts. The preferred route to date, based on the procedure of Ueda, utilizes methanesulfonic acid as solvent and catalyst. Model compounds containing two propenone linkages were synthesized from 1,4-DAB and benzaldehyde and from iPhal and tPhal and acetophenone. In some cases, based on GC-MS analysis, primarily mono adduct was formed in the model compound work. Yields of polymers and model compounds were generally in the 70-85% range. All tenaciously held water and were insoluble in the usual solvents precluding NMR analysis. IR showed some ketol functionality. Products have been characterized by IR, dsc and tga. The synthesis of amino, pyridyl, and hydroxy-substituted chalcones is underway with the goal of optimizing chalcone formation. It is hoped this wil permit synthesis of industrially useful polymers.