Fluorophore-Appendant 5,5′-Bicalixarene Scaffolds for Host–Guest Sensing of Nitric Oxide

[Image: see text] Conjugated 5,5′-Bicalixarene scaffolds having fluorophores at the chain termini have been prepared and tested in the supramolecular detection of nitric oxide. Scaffolds bearing electron-rich fluorophores demonstrated a stronger turn-off response to the presence of NO than the fluorophore-free analogue in both organic and aqueous media, while no fluorescence quenching happened when the electron-deficient fluorophores were employed. Unprecedented ratiometric supramolecular sensing was observed when fluorophores of the opposite electronic demands were placed at the scaffold’s termini.