Unusual Reactivity and Metal Affinity of Water-Soluble Dipyrrins.

ABSTRACT: Dipyrrins are a versatile class of organic ligands capable of fluorogenic complexation of metal ions. The primary goal of our study was to evaluate dipyrrins functionalized with ester and amide groups in 2,2'-positions in sensing applications. While developing the synthesis, we found that 3,3',4,4'-tetraalkyldipyrrins 2,2'-diesters as well as 2,2'-diamides can undergo facile addition of water at the meso-bridge, transforming into colorless meso-hydroxydipyrromethanes. Spectroscopic and computational investigation revealed that this transformation proceeds via dipyrrin cations, which exist in equilibrium with the hydroxydipyrromethanes. While trace amounts of acid favor conversion of dipyrrins to hydroxydipyrromethanes, excess acid shifts the equilibrium toward the cations. Si

SUBMITTER: El Khatib M 

PROVIDER: S-EPMC10178602 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature