Pyreno[2,1-b]pyrrole and bis(pyreno[2,1-b]pyrrole) as selective chemosensors of fluoride ion: a mechanistic study.

Pyreno[2,1-b]pyrrole and its dimeric derivative display excellent selectivity and sensitivity for detection of fluoride ion, in comparison with chloride, bromide, iodide, acetate, dihydrogen phosphate, hydrogen sulfate, perchlorate, nitrate, and thiocyanate ions. The hydrogen bonding with fluoride ion, both in formation and in subsequent dissociation, provides remarkable colorimetric and fluorescent changes in the visible region that are advantageous for real-time and on-site application. Detailed NMR and dynamic fluorescence spectroscopic analyses establish the associated mechanism.