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1,1′‐Ferrocenylene‐Bridged Bis(N‐Heterocyclic Olefin) Derivatives
Author(s) -
Guthardt Robin,
Mellin Johanna,
Bruhn Clemens,
Siemeling Ulrich
Publication year - 2022
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.202100903
Subject(s) - chemistry , imes , ferrocene , carbene , cyclic voltammetry , denticity , medicinal chemistry , olefin fiber , ligand (biochemistry) , redox , diastereomer , stereochemistry , electrochemistry , crystal structure , crystallography , organic chemistry , catalysis , electrode , biochemistry , receptor
The 1,1′‐ferrocenylene (fc)‐bridged bis(N‐heterocyclic olefin) compounds (IMes=CH) 2 fc ( 1 , IMes=1,3‐dimesitylimidazolin‐2‐ylidene) and (IPr=CH) 2 fc ( 2 , IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazolin‐2‐ylidene) were synthesised from (ICH 2 ) 2 fc ( 3 ) and the respective N‐heterocyclic carbene IMes or IPr. Ligand substitution reactions of 1 and 2 with [BH 3 (THF)] afforded the complexes [ 1 (BH 3 ) 2 ] and [ 2 (BH 3 ) 2 ] as mixtures of the rac ‐ and meso ‐diastereomers. The new ferrocene derivatives 1 – 3 and the complexes meso ‐[ 1 (BH 3 ) 2 ], rac ‐[ 1 (BH 3 ) 2 ] and rac ‐[ 2 (BH 3 ) 2 ] were structurally characterised by single‐crystal X‐ray diffraction. 1 and 2 represent a new class of ferrocene‐based, and hence redox‐active, bidentate ligands. The presence of three redox‐active moieties, viz. the ferrocene unit and the two NHO units, is reflected by three consecutive oxidations according to an electrochemical investigation exemplarily performed with 2 by cyclic voltammetry.