Synthetic access to calix[3]pyrroles via meso-expansion: hosts with diverse guest chemistry

Calix[3]pyrroles were synthesized for the first time. These macrocycles display versatile guest binding ability based on the bridges connecting the two alpha-positions of the tripyrrane moiety e.g. with an ethene bridge they showed colorimetric sensing of fluoride and cyanide ions, whereas with a phenylene spacer they exhibited fluorometric sensing of fluoride ions only, and the macrocycle with an ethylene unit acted as a host towards the water molecule with unique penta-coordinated oxygen in the solid state.