Coordination Chemistry of a Bis(Tetrazine) Tweezer: A Case of Host-Guest Behavior with Silver Salts
| Autor: | Jean-Cyrille Hierso, Michel Meyer, Hélène Cattey, Charles H. Devillers, Paul Fleurat-Lessard, Taoufik Boubaker, Clève D. Mboyi, Ons Amamou, Julien Roger |
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| Přispěvatelé: | Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon] (ICMUB), Centre National de la Recherche Scientifique (CNRS)-Université de Bourgogne (UB)-Institut de Chimie du CNRS (INC), Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité [Monastir] (CHPNR), Département de Chimie [Monastir], Faculté des Sciences de Monastir (FSM), Université de Monastir - University of Monastir (UM)-Université de Monastir - University of Monastir (UM)-Faculté des Sciences de Monastir (FSM), Université de Monastir - University of Monastir (UM)-Université de Monastir - University of Monastir (UM) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
analytical_chemistry
coordination Absorption spectroscopy Pharmaceutical Science Crystal structure 010402 general chemistry Electrochemistry ligand 01 natural sciences Article XRD structure Analytical Chemistry Coordination complex Tetrazine chemistry.chemical_compound QD241-441 bis(tetrazine) Drug Discovery [CHIM.CRIS]Chemical Sciences/Cristallography [CHIM.COOR]Chemical Sciences/Coordination chemistry silver Physical and Theoretical Chemistry host-guest chemistry.chemical_classification 010405 organic chemistry Ligand Organic Chemistry Cationic polymerization 0104 chemical sciences Crystallography chemistry Chemistry (miscellaneous) Molecular Medicine Stoichiometry |
| Zdroj: | Molecules Molecules, Vol 26, Iss 2705, p 2705 (2021) Volume 26 Issue 9 Molecules, MDPI, 2021, 26 (9), pp.2705. ⟨10.3390/molecules26092705⟩ |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules26092705⟩ |
| Popis: | The carbon-carbon cross-coupling of phenyl s-tetrazine (Tz) units at their ortho-phenyl positions allows the formation of constrained bis(tetrazines) with original tweezer structures. In these compounds, the face-to-face positioning of the central tetrazine cores is reinforced by π-stacking of the electron-poor nitrogen-containing heteroaromatic moieties. The resulting tetra-aromatic structure can be used as a weak coordinating ligand with cationic silver. This coordination generates a set of bis(tetrazine)-silver(I) coordination complexes tolerating a large variety of counter anions of various geometries, namely, PF6−, BF4−, SbF6−, ClO4−, NTf2−, and OTf−. These compounds were characterized in the solid state by single-crystal X-ray diffraction (XRD) and diffuse reflectance spectroscopy, and in solution by 1H-NMR, mass spectrometry, electroanalysis, and UV-visible absorption spectrophotometry. The X-ray crystal structure of complexes {[Ag(3)][PF6]}∞ (4) and {[Ag(3)][SbF6]}∞ (6), where 3 is 3,3′-[(1,1′-biphenyl)-2,2′-diyl]-6,6′-bis(phenyl)-1,2,4,5-tetrazine, revealed the formation of 1D polymeric chains, characterized by an evolution to a large opening of the original tweezer and a coordination of silver(I) via two chelating nitrogen atom and some C=C π-interactions. Electrochemical and UV spectroscopic properties of the original tweezer and of the corresponding silver complexes are reported and compared. 1H-NMR titrations with AgNTf2 allowed the determination of the stoichiometry and apparent stability of two solution species, namely [Ag(3)]+ and [Ag(3)2]2+, that formed in CDCl3/CD3OD 2:1 v/v mixtures. |
| Databáze: | OpenAIRE |
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