Intra- and intermolecular hydrogen bonds in pyrrolylindandione derivatives and their interaction with fluoride and acetate: possible anion sensing properties.

The series of push-pull compounds containing the pyrrole ring as a donor and the 1,3-indandione derived moieties as the acceptor unit were synthesized, and strong intramolecular hydrogen bonding in their molecules was studied. In the presence of fluoride and acetate anions their solutions undergo color changes. It was shown by NMR, UV-vis, and quantum chemical calculations including AIM analysis that all these compounds undergo solvent-assisted rupture of the intramolecular hydrogen bond followed by the formation of a strong intermolecular hydrogen bond with fluoride and acetate anions which finally abstract a proton from the pyrrole ring. The insensitivity of the studied compounds to other anions (Cl, Br, HSO4, PF6) is consequence of the instability of the corresponding hydrogen-bonded complexes.