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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 M2+ 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 M2+ ions, remarking Ni2+ as the most interesting phenomenon. These results project the compounds as potential colorimetric receptors for nickel ions in complex solutions.

Instituto de Investigaciones Químico Biológicas. Doctorado en Ciencias Químicas Natural occurring products are an enormous source of chemical structures. These fine and intricate molecules are an inspiration for synthetic researchers not only by their bioactive properties but also because of the distribution of their functional groups that allow them to be used as a chemical template for more complex compounds. In this sense, we can build synthetic hybrids with a “bottom-up” order that can accomplish functions at the nanoscale as molecular switches, interacting with specific energetic stimuli and resulting in a work response. This work is an effort to synthesize molecular switches by hybridization with natural occurring quinones such as perezone and synthetic azobenzene photochromic species, or even molecular blocks with proved supramolecular properties, such as pyrrole and its derivatives. Los compuestos de origen natural son una gran fuente de estructuras químicas. Estas intrincadas y finas estructuras inspiran a los químicos sintéticos, no sólo por la bioactividad que presentan, sino por la distribución de sus grupos funcionales que permiten su empleo como plantillas moleculares. En este sentido podemos construir híbridos con un orden de construcción “desde abajo” que puedan desempeñar funciones a nanoescala como interruptores moleculares, interactuando con estímulos energéticos específicos y traduciendo estos en trabajo como respuesta. Este trabajo es un intento de llevar a síntesis interruptores moleculares por hibridación entre quinonas de origen natural como la perezona y especies fotocrómicas sintéticas como los azobencenos, así como bloques sintéticos de probadas propiedades supramoleculares como el pirrol y sus derivados.

We describe the synthesis of the novel 2-(1,5-dimethyl-4-oxo-hexyl)-3-hydroxy-5-methyl-6-pyrrolyl-1,4-benzoquinone 2 from the natural product perezone 1. The anion–guest properties of the new compound were evaluated in the presence of fluoride, chloride, bromide and iodide tetrabutylammonium salts using 1H NMR titration techniques in deuterated dichloromethane or dimethylformamide. The title compound showed interesting colorimetric behavior in the presence of inorganic salts.