A novel chiroptical phenomenon named "chiroptical rhythmicity" is described. Chiroptical rhythmicity consists of multiple reversible circular dichroism Cotton effect sign inversions that follow a rhythmical pattern with respect to the continuous addition of a ligand (L-His) to the sample (a septi(p-phenylene)-based receptor bound to phosphatidylcholine bilayers). Decrease and blue-shift of the 1La absorption of the oligophenylene chromophore indicated that partial "H" aggregation occurs during chiroptical rhythmicity. Based on stereochemical considerations for monomeric and tetrameric oligophenylenes, a hypothetical mechanism is discussed.