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Chiral and Redox‐Active Room‐Temperature Ionic Liquids Based on Ferrocene and l ‐Proline
Author(s) -
Bouvet Carola B.,
Krautscheid Harald
Publication year - 2016
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201600585
Subject(s) - chemistry , ferrocene , iodide , ionic liquid , solvent , diastereomer , redox , electrochemistry , inorganic chemistry , methylene , alkyl , medicinal chemistry , ionic bonding , ion , organic chemistry , catalysis , electrode
The syntheses of room‐temperature ionic liquids (RTILs) combining the naturally occurring amino acid l ‐proline and ferrocene (Fc) building blocks are reported. After quaternization of ({[(2 S )‐ N ‐methylpyrrolidine‐2‐yl]methyleneoxy}carbonyl)ferrocene ( 1 ) with alkyl iodides and anion exchange, the resulting diastereomeric (1 S ,2 S )‐ and (1 R ,2 S )‐[(ferrocenylcarbonyl)oxy]methylene‐ N , N ‐dialkylpyrrolidine‐1‐ium RTILs are redox‐active and air‐ and water‐stable. They are also thermally stable up to 263 °C. The electrochemical Fe II /Fe III potential is shifted to +0.28 V versus Fc/Fc + . Before anion exchange, several iodide derivatives were obtained as crystalline products, and their crystal structures are reported. According to the NMR spectroscopic data cation–anion aggregates are present in the non‐coordinating solvent CDCl 3 . In contrast, in the polar solvent [D 6 ]dimethyl sulfoxide ([D 6 ]DMSO), the ion pairs are separated.