Friedel-crafts copolymerization of thiophene and p-di(chloromethyl)benzene. II. Products of the later stages of the reaction

Products of the copolymerization of thiophene and p-di(coloromethyl)benzene in presence of stannic chloride have been separated by using gel-permeation chromatography (GPC) and identified by using principally mass, infrared, and nuclear magnetic resonance spectroscopy. The GPC separation is not nearly as efficient as the separation of the products of the corresponding benzene–DCMB and diphenylmethane–DCMB reactions which have previously been described. A further complication which makes a kinetic analysis of this reaction more difficult is the occurrence of intramolecular condensation of certain of the earlier products leading to cyclic structures incorporating four aromatic rings. These investigations have made it possible to deduce some of the principal structural differences between the thiophene–DCMB and benzene–DCMB polymers which may have some bearing on the differences which have been found in their thermal stabilities.