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An expedient regioselectivesynthesis of novel mono, C2-symmetric bis-triazole and acridinedione bridged macromolecules has been achieved in good yields employing intermolecular Cu(I) catalyzed azide and alkyne click reaction. Synthesis of O-propargyl acridinedione was achieved in three good yielding steps starting from dimedone, while the symmetrical aliphatic and aryl bis-azides were derived from appropriate dibromides in the presence of sodium azide in dry DMF. The synthesized mono and C2-symmetric bis-macromolecules have been elucidated by 1H, 13C, elemental and mass spectroscopic analysis. The antioxidant activity of synthesized compounds has also been investigated.