An Investigation into Anion Sensing of the Molecular Aggregate of 4-(Pyrrol-1-yl)pyridine and Its Derivatives.

Recently, 4-(pyrrol-1-yl)pyridine has been found to act as a supramolecular chemodosimeter, sensing nitrite ions in an aqueous solution with naked eye detection and a low limit of detection of 0.330 ppm. This work explores the anion-sensing properties of related derivatives, 4-(2,5-dimethyl-pyrrol-1-yl)pyridine and 4-(2,4-dimethyl-pyrrol-1-yl)pyridine, and provides a comparison with the parent compound. These molecules are determined to be effective sensors for nitrite ions with limits of detection of 1.06 ppm and 1.05 ppm, respectively. The high sensitivity and selectivity to nitrite remain even in the presence of competing anions such as SO, NO, PO, SO, Cl, F, I, Br, AcO, and CN. Analogous to the 4-(pyrrol-1-yl)pyridine system, the sensing mechanism appears to be the result of changes in the supramolecular aggregate system upon the interaction of an anion; this is further explored through dynamic light scattering, the Tyndall effect, and NMR spectroscopy. The two methylated derivative systems reported herein, 4-(2,5-dimethyl-pyrrol-1-yl)pyridine and 4-(2,4-dimethyl-pyrrol-1-yl)pyridine, are shown to affect the size of the supramolecular system and provide further insight into the unique mechanism of action.