Chloride Binding Modulated by Anion Receptors Bearing Tetrazine and Urea

Romain Plais (1, 2, 3, 4) , Guy Gouarin (1, 2, 3, 4) , Amélie Bournier (2, 5, 6, 7, 4) , Olfa Zayene (2, 1, 3, 4) , Vanessa Mussard (2, 1, 3, 4) , Flavien Bourdreux (2, 1, 3, 4) , Jérome A Marrot (2, 1, 3, 4) , Arnaud Brosseau (2, 8, 9, 4) , Anne Gaucher (2, 3, 1, 4) , Gilles Clavier (2, 9, 8, 4) , Jean‐yves Salpin (2, 5, 6, 7, 4) , Damien Prim (2, 1, 3, 4)

1 ILV - Institut Lavoisier de Versailles
2 Université Paris-Saclay
3 UVSQ - Université de Versailles Saint-Quentin-en-Yvelines
4 CNRS - Centre National de la Recherche Scientifique
5 LAMBE - UMR 8587 - Laboratoire Analyse, Modélisation et Matériaux pour la Biologie et l'Environnement
6 UEVE - Université d'Évry-Val-d'Essonne
7 CY - CY Cergy Paris Université
8 PPSM - Photophysique et Photochimie Supramoléculaires et Macromoléculaires
9 ENS Paris Saclay - Ecole Normale Supérieure Paris-Saclay

Modulation and fine-tuning of the strength of weak interactions to bind anions are described in a series of synthetic receptors. The general design of the receptors includes both a urea motif and a tetrazine motif. The synthetic sequence towards three receptors is detailed. Impacts of H-bond strength and linker length between urea and tetrazine on chloride complexation are studied. Binding properties of the chloride anion are examined in both the ground and excited states using a panel of analytical methods (NMR spectroscopy, mass spectrometry, UV/Visible spectroscopies, and fluorescence). A ranking of the receptors by complexation strength has been determined, allowing a better understanding of the structure-properties relationship on these compounds.

Domains: Theoretical and/or physical chemistry; Analytical chemistry; Cheminformatics; Chemical Sciences; Chemical Physics [physics.chem-ph]

Romain Plais, Guy Gouarin, Amélie Bournier, Olfa Zayene, Vanessa Mussard, et al.. Chloride Binding Modulated by Anion Receptors Bearing Tetrazine and Urea. ChemPhysChem, 2022, ⟨10.1002/cphc.202200524⟩. ⟨hal-03854582⟩