《Unusual Reactivity and Metal Affinity of Water-Soluble Dipyrrins》 was written by El Khatib, Mirna; Cheprakov, Andrei V.; Vinogradov, Sergei A.. Recommanded Product: 26153-38-8This research focused onwater soluble dipyrrin preparation metal affinity. The article conveys some information:
The primary goal of the study was to evaluate dipyrrins functionalized with ester and amide groups in 2,2′-positions in sensing applications. While developing the synthesis, it was 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. Similarly, the presence of Zn2+ facilitates elimination of water from hydroxydipyrromethanes with chromogenic regeneration of the dipyrrin system. In organic solutions in the presence of Zn2+, dipyrrin-2,2′-diesters exist as mixtures of mono-(LZnX) and bis-(L2Zn) complexes. In L2Zn, the dipyrrin ligands are oriented in a nonorthogonal fashion, causing strong exciton coupling. In aqueous solutions, dipyrrins bind Zn2+ in a 1:1 stoichiometry, forming mono-dipyrrinates (LZnX). Unexpectedly, dipyrrins with more electron-rich 2,2′-carboxamide groups revealed ~20-fold lower affinity for Zn2+ than the corresponding 2,2′-diesters. D. Functional Theory (DFT) calculations with explicit inclusion of water reproduced the observed trends and allowed to trace the low affinity of the dipyrrin-diamides to the stabilization of the corresponding free bases via hydrogen bonding with water mols. Overall, the results reveal unusual trends in the reactivity of dipyrrins and provide clues for the design of dipyrrin-based sensors for biol. applications.3,5-Dihydroxybenzaldehyde(cas: 26153-38-8Recommanded Product: 26153-38-8) was used in this study.
3,5-Dihydroxybenzaldehyde(cas: 26153-38-8) is a building block. It has been used in the synthesis of 2,4-dimethylbenzoylhydrazones with antileishmanial and antioxidant activities.Recommanded Product: 26153-38-8
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