Methylazacalix[4]pyridine: en route to Zn2+-specific fluoresence sensors.

[structure: see text] Owing to the electronic nature of the bridging nitrogen atoms which can adopt different hybridizations and form various conjugations with the adjacent pyridine(s), methylazacalix[4]pyridine underwent conformation and cavity preorganization to highly selectively bind the Zn(2+) ion. Rigidification and coplanarity of the macrocyclic ring led to a great enhancement of fluorescence of the intrinsic fluorescent host molecule.