Synthesis of chiral permanent fluorophoric biscyclic macrocycles incorporating anthraquinone and (S)-BINOL core is described. Interestingly, the biscyclic macrocycle 1 exhibited remarkable antibacterial activity against most of the pathogenic bacteria in the tested concentrations as compared to the other three compounds 2, 14 and 17 as well as the test control, tetracycline. Further biscyclophanes 1 and 2 exhibited permanent fluorescence sensing property even under highly acidic conditions.