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A series of copolymers containing oxadiazole and fluorene cromophores was synthesized by polycondensation of a diacid chloride incorporating one diphenylsilane linkage and a mixture of aromatic diamines containing oxadiazole and fluorene moieties. The solubility, thermal behavior, and photoluminescence ability of the thin polymer films were studied and compared with related heterocyclic polymers. These polymers are semicrystalline and form plastic mesophases in the first heating run, which brings about new ordered melted state processing opportunities. They exhibited blue photoluminescence in nanometric films, thus being promising candidates for manufacturing electroluminescent devices.