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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 SO32−, NO32−, PO43−, SO42−, 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. [ABSTRACT FROM AUTHOR]

With increasing concerns over environmental impact and overall health of both the environment and its people, a need to quantify contaminants is of the utmost importance. Chemosensors with low detection limits and a relative ease of application can address this challenge. Nitrite ions are known to be detrimental to both the environment and human health. A new colorimetric chemodosimeter has been prepared from the homolytic photochemical cleavage of a reaction between pyrrole and pyridine. The product, 4-(pyrrol-1-yl)pyridine, yields a limit of detection of 0.330 (±0.09) ppm for the detection of nitrite in aqueous solution, employing a colorimetric change from yellow to pink. It is also highly selective for nitrite when various competitive anions such as SO 3 2- , NO 3 - , PO 4 3- , SO 4 -2 , Cl - , F - , I - , Br - , AcO - , and CN - are present in great excess. The molecule's especially high sensitivity to nitrite is apparently the result of a complex supramolecular mechanism, characterized by both dynamic light scattering of the aggregate and the Tyndall effect. Consequently, this new sensor provides a simple, low-cost way to rapidly detect nitrite anions in aqueous solution., Competing Interests: The authors declare no competing financial interest., (© 2024 The Authors. Published by American Chemical Society.)