The use of CO as a C1 carbon source for synthesis is raising increasing attention both as a strategy to bring value to carbon dioxide capture technologies and a sustainable approach towards chemicals and energy. The presented results focus on the application of electrochemical methods to incorporate CO into organic compounds using ionic liquids as electrolytes, which provides a green alternative to the formation of C-C bonds. In this sense, the current manuscript shows that Naproxen (6-Methoxy-α-methyl-2-naphthaleneacetic acid) can be synthetizing in high yield (89%) and conversion rates (90%) through an electrocarboxylation process using CO and ionic liquids.
View Article and Find Full Text PDFElectrocarboxylation of organic halides is one of the most widely used approaches for valorising CO. In this manuscript, we report a new greener synthetic route for synthesising 2-(4-isobutylphenyl)propanoic acid, Ibuprofen, one of the most popular non-steroidal anti-inflammatory drugs (NSAIDs). The joint use of electrochemical techniques and ionic liquids (ILs) allows CO to be used as a C-organic building block for synthesising Ibuprofen in high yields, with conversion ratios close to 100%, and under mild conditions.
View Article and Find Full Text PDFFluorescent switches based on spirocyclic zwitterionic Meisenheimer (SZMC) complexes are stimuli-responsive organic molecules with application in a variety of areas. To expand their functionality, novel switching mechanisms are herein reported for these systems: (a) acid- and redox-triggered formation of an additional protonation state with distinct optical properties, and (b) solvent-induced fluorescence modulation. We demonstrate that these new features, which enable both multistimuli and multistate operation of SZMC switches, can be exploited in the preparation of smart organic materials: wide-range pH optical probes, electrochromic and electrofluorochromic films, and polymer-based fluorescent detectors of organic liquids.
View Article and Find Full Text PDFThe binding and electrochemical properties of the complexes Cu -HAH, Cu -HWH, Cu -Ac-HWH, Cu -HHW, and Cu -WHH have been studied by using NMR and UV/Vis spectroscopies, CV, and density functional calculations. The results obtained highlight the importance of the peptidic sequence on the coordination properties and, consequently, on the redox properties of their Cu complexes. For Cu -HAH and Cu -HWH, no cathodic processes are observed up to -1.
View Article and Find Full Text PDFStable zwitterionic spirocyclic Meisenheimer compounds were synthesized using a one-step reaction between picric acid and diisopropyl (ZW1) or dicyclohexyl (ZW3) carbodiimide. A solution of these compounds displays intense orange fluorescence upon UV or visible light excitation, which can be quenched or "turned-off" by adding a mole equivalent amount of F or CN ions in acetonitrile. Fluorescence is not quenched in the presence of other ions such as Cl, Br, I, NO₂, NO₃, or H₂PO₄.
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