title: First Occurrence of Tetrazines in Aqueous Solution: Electrochemistry and Fluorescence.
abstract: The photophysical and electrochemical properties of tetrazines substituted by linear 2,3-naphtalimide antennas and/or adamantane groups specifically dedicated to host-guest interactions with cyclodextrins are studied both in organic and aqueous media. In acetonitrile solvent, the reduction potential of tetrazine leading to the anion radical is shifted, depending on the electron-withdrawing power of the substituent of the tetrazines. Due to the hydrophobic character of these compounds, their solubilization in aqueous solution is achieved successively in presence of either β-cyclodextrins or gold nanoparticules modified by β-cyclodextrins. We demonstrate that the formation of the inclusion compound tetrazine-cyclodextrin allows the solubilization of the tetrazines in aqueous solution. The supramolecular assemblies obtained in water retain tetrazine's emission properties, yielding a yellow fluorescence.
authors.affiliation: DCM UMR 5250, University Grenoble Alpes, F-38000, Grenoble, France.|Analytical Chemistry Department, Faculty of Pharmacy, "Iuliu Haţieganu", University of Medicine and Pharmacy, 4 Pasteur, 400349, Cluj-Napoca, Romania.
authors.forename: Luminiţa
authors.initials: L
authors.lastname: Fritea
authors.affiliation: PPSM, CNRS UMR 8531, ENS Cachan, 61 Avenue du Président Wilson, 94235, Cachan, France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Audebert
authors.affiliation: PPSM, CNRS UMR 8531, ENS Cachan, 61 Avenue du Président Wilson, 94235, Cachan, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Galmiche
authors.affiliation: DCM UMR 5250, University Grenoble Alpes, F-38000, Grenoble, France.
authors.forename: Karine
authors.initials: K
authors.lastname: Gorgy
authors.affiliation: DCM UMR 5250, University Grenoble Alpes, F-38000, Grenoble, France.
authors.forename: Alan
authors.initials: A
authors.lastname: Le Goff
authors.affiliation: Dpto de Química Analítica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040, Madrid, Spain.
authors.forename: Reynaldo
authors.initials: R
authors.lastname: Villalonga
authors.affiliation: Analytical Chemistry Department, Faculty of Pharmacy, "Iuliu Haţieganu", University of Medicine and Pharmacy, 4 Pasteur, 400349, Cluj-Napoca, Romania.
authors.forename: Robert
authors.initials: R
authors.lastname: Săndulescu
authors.affiliation: DCM UMR 5250, University Grenoble Alpes, F-38000, Grenoble, France. serge.cosnier@ujf-grenoble.fr.
authors.forename: Serge
authors.initials: S
authors.lastname: Cosnier
keywords: cyclodextrin; gold nanoparticles; host-guest interactions; supramolecular assembly; tetrazine