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Synthesis and Characterization of New Ferrocene‐Containing Ionic Liquids
Author(s) -
Gharib Bhasem,
Hirsch Andreas
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400061
Subject(s) - ferrocene , chemistry , moiety , amide , acylation , alkyl , counterion , ionic liquid , nuclear magnetic resonance spectroscopy , organic chemistry , triflic acid , methanol , polymer chemistry , catalysis , electrochemistry , ion , electrode
A series of several new families of ferrocene‐containing imidazolium salts were synthesized by etherification of ferrocene methanol, acylation of ferrocene, and amide coupling of ferrocene carboxylic acid. The etherification was achieved by an acid‐catalyzed procedure and very good yields of between 86–93 % were obtained. Next to the nature of the linkage itself, the lengths of the alkyl chains linking the ferrocenyl moiety and the imidazolium group and the nature of the counterions were also varied. Interestingly, a γ‐effect can be observed for the ether compounds but this effect was only visible in 13 C NMR spectroscopy. These new redox‐active ionic liquids were fully characterized by FTIR, 1 H, 19 F, and 13 C NMR spectroscopy, and by MS, HRMS and elemental analysis.