Long Range Electronic Effects on the Host–Guest Complexation within the Oxygen Depleted 5,5′-Bicalixarene Cavities

[Image: see text] We report the synthesis of a series of the oxygen-depleted conjugated 5,5′-Bicalix[4]arene compounds bearing various substituents at the terminal positions of the conjugated chain and their fluorescence response to the presence of a cationic N-methylpyridinium guest. The complexation of this cation within the bicalixarene cavity results in the fluorescence quenching, with the host molecules bearing electron-donating groups demonstrating a stronger fluorescence response. These results show the importance of the electronic effects on the host–guest complexation within the hydrophobic calixarene scaffolds.