The intramolecular cyclization of alpha-carboxyl, omega-amino heterodifunctional polystyrene was carried out to obtain cyclic polystyrene having an amide moiety in the main chain. The amide moiety was reduced with lithium aluminum hydride to give macrocyclic amine. The reactions of the macrocyclic amine with carboxylic-terminated polystyrene and glutaric acid gave tadpole- and eight-shaped polystyrenes, respectively. These macromolecular architectures were characterized by NMR, IR, and GPC analysis.