Abstract A new conjugated Schiff base macrocycle containing 1,3,4-oxadiazole ring was prepared by elimination of a tosyl group from a sulfonamide under basic conditions. This synthetic method will provide access to a wide variety of novel conjugated Schiff base macrocycles. The reaction mechanism was examined. The macrocycle has a highly conjugated ring structure and high thermal stability and was doped with iodine to form a stable conducting complex with a conductivity of 10 −2 S/cm. It can be used as semiconductive material.