Cooperative Recognition of Ni²⁺ Triggered by Fluoride Ions in Naturally Occurring α-Hydroxyquinone Derivatives

Abstract

Perezone is a naturally occurring hydroxyquinone that has been deeply studied from different chemical aspects, such as therapeutics, electrochemistry, physical–chemical properties, or synthetic approaches that turn it an attractive template for new semisynthetic derivatives with a wide range of purposes. Herein, we describe a facile synthetic pathway to obtain new perezone derivatives by the addition of a pyrrole moiety that can be used for ion recognition. Compounds 2–4 showed the capability to interact with several anions and M 2+ cations as separate events that result in colorimetric changes. Moreover, the compounds can behave as heteroditopic receptors. Besides, a previous interaction between fluoride ions and perezone derivatives triggered a successful recognition of M 2+ ions, remarking Ni 2+ as the most interesting phenomenon. These results project the compounds as potential colorimetric receptors for nickel ions in complex solutions.