NHC Versus Pyridine: How “Teeth” Change the Redox Behavior of Iron(II) Complexes

Daniel T. Weiss; Markus R. Anneser; Stefan Haslinger; Alexander Pöthig; Mirza Cokoja; Jean-Marie Basset; Fritz E. Kühn

doi:10.1021/acs.organomet.5b00732

NHC Versus Pyridine: How “Teeth” Change the Redox Behavior of Iron(II) Complexes

Daniel T. Weiss, Markus R. Anneser, Stefan Haslinger, Alexander Pöthig, Mirza Cokoja, Jean-Marie Basset, Fritz E. Kühn

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

A series of octahedral iron(II) complexes with tetradentate NHC/pyridine hybrid ligands containing up to three pyridyl units was designed to study the influence of NHC and pyridine donors on the electronic structure of the metal center. Structural analysis of the iron complexes by NMR spectroscopy and single-crystal X-ray diffraction reveals different coordination modes of the ligand depending on the linkage of the different donor moieties. The oxidation potentials of all complexes correlate linearly with the number of NHC moieties coordinated to iron, as shown by cyclic voltammetry. The influence, although minor, of structural properties on the oxidation potential and (in one case) the influence of the oxidation state of the coordination geometry of the hybrid ligand are also demonstrated.

Original language	English (US)
Pages (from-to)	5155-5166
Number of pages	12
Journal	Organometallics
Volume	34
Issue number	20
DOIs	https://doi.org/10.1021/acs.organomet.5b00732
State	Published - Oct 6 2015

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CCDC 1420289: Experimental Crystal Structure Determination : (2,2'-(methylenebis(1H-imidazol-2-ylidene-3,1(2H)-diylmethylene))dipyridine)-tris(acetonitrile)-iron bis(hexafluorophosphate) diethyl ether solvate
Weiss, D. T. (Creator), Anneser, M. R. (Creator), Haslinger, S. (Creator), Pöthig, A. (Creator), Cokoja, M. (Creator), Basset, J. (Creator), Kühn, F. E. (Creator), Weiss, D. T. (Creator), Anneser, M. R. (Creator), Haslinger, S. (Creator), Pöthig, A. (Creator), Cokoja, M. (Creator) & Kühn, F. E. (Creator), Cambridge Crystallographic Data Centre, Oct 28 2015
DOI: 10.5517/cc1jnxsw, http://hdl.handle.net/10754/624468
Dataset
CCDC 1420290: Experimental Crystal Structure Determination : (6,6'-bis((3-methyl-2,3-dihydro-1H-imidazol-2-ylidene-1-yl)methyl)-2,2'-bipyridine)-bis(acetonitrile)-iron bis(hexafluorophosphate) acetonitrile solvate
Weiss, D. T. (Creator), Anneser, M. R. (Creator), Haslinger, S. (Creator), Pöthig, A. (Creator), Cokoja, M. (Creator), Basset, J. (Creator), Kühn, F. E. (Creator), Weiss, D. T. (Creator), Anneser, M. R. (Creator), Haslinger, S. (Creator), Pöthig, A. (Creator), Cokoja, M. (Creator) & Kühn, F. E. (Creator), Cambridge Crystallographic Data Centre, Oct 28 2015
DOI: 10.5517/cc1jnxtx, http://hdl.handle.net/10754/624469
Dataset
CCDC 1420291: Experimental Crystal Structure Determination : (2-(3-((3-((3-methyl-2,3-dihydro-1H-imidazol-2-ylidene-1-yl)methyl)-2,3-dihydro-1H-imidazol-2-ylidene-1-yl)methyl)-2,3-dihydro-1H-imidazol-2-ylidene-1-yl)pyridine)-bis(acetonitrile)-iron bis(hexa
Weiss, D. T. (Creator), Anneser, M. R. (Creator), Haslinger, S. (Creator), Pöthig, A. (Creator), Cokoja, M. (Creator), Basset, J. (Creator), Kühn, F. E. (Creator), Weiss, D. T. (Creator), Anneser, M. R. (Creator), Haslinger, S. (Creator), Pöthig, A. (Creator), Cokoja, M. (Creator) & Kühn, F. E. (Creator), Cambridge Crystallographic Data Centre, Oct 28 2015
DOI: 10.5517/cc1jnxvy, http://hdl.handle.net/10754/624470
Dataset

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title = "NHC Versus Pyridine: How “Teeth” Change the Redox Behavior of Iron(II) Complexes",

abstract = "A series of octahedral iron(II) complexes with tetradentate NHC/pyridine hybrid ligands containing up to three pyridyl units was designed to study the influence of NHC and pyridine donors on the electronic structure of the metal center. Structural analysis of the iron complexes by NMR spectroscopy and single-crystal X-ray diffraction reveals different coordination modes of the ligand depending on the linkage of the different donor moieties. The oxidation potentials of all complexes correlate linearly with the number of NHC moieties coordinated to iron, as shown by cyclic voltammetry. The influence, although minor, of structural properties on the oxidation potential and (in one case) the influence of the oxidation state of the coordination geometry of the hybrid ligand are also demonstrated.",

author = "Weiss, {Daniel T.} and Anneser, {Markus R.} and Stefan Haslinger and Alexander P{\"o}thig and Mirza Cokoja and Jean-Marie Basset and K{\"u}hn, {Fritz E.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: D.T.W. and S.H. gratefully acknowledge support from the TUM Graduate School.",

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AU - Weiss, Daniel T.

AU - Anneser, Markus R.

AU - Haslinger, Stefan

AU - Pöthig, Alexander

AU - Cokoja, Mirza

AU - Basset, Jean-Marie

AU - Kühn, Fritz E.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: D.T.W. and S.H. gratefully acknowledge support from the TUM Graduate School.

PY - 2015/10/6

Y1 - 2015/10/6

N2 - A series of octahedral iron(II) complexes with tetradentate NHC/pyridine hybrid ligands containing up to three pyridyl units was designed to study the influence of NHC and pyridine donors on the electronic structure of the metal center. Structural analysis of the iron complexes by NMR spectroscopy and single-crystal X-ray diffraction reveals different coordination modes of the ligand depending on the linkage of the different donor moieties. The oxidation potentials of all complexes correlate linearly with the number of NHC moieties coordinated to iron, as shown by cyclic voltammetry. The influence, although minor, of structural properties on the oxidation potential and (in one case) the influence of the oxidation state of the coordination geometry of the hybrid ligand are also demonstrated.

AB - A series of octahedral iron(II) complexes with tetradentate NHC/pyridine hybrid ligands containing up to three pyridyl units was designed to study the influence of NHC and pyridine donors on the electronic structure of the metal center. Structural analysis of the iron complexes by NMR spectroscopy and single-crystal X-ray diffraction reveals different coordination modes of the ligand depending on the linkage of the different donor moieties. The oxidation potentials of all complexes correlate linearly with the number of NHC moieties coordinated to iron, as shown by cyclic voltammetry. The influence, although minor, of structural properties on the oxidation potential and (in one case) the influence of the oxidation state of the coordination geometry of the hybrid ligand are also demonstrated.

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UR - https://pubs.acs.org/doi/10.1021/acs.organomet.5b00732

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JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 20

ER -

NHC Versus Pyridine: How “Teeth” Change the Redox Behavior of Iron(II) Complexes

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CCDC 1420289: Experimental Crystal Structure Determination : (2,2'-(methylenebis(1H-imidazol-2-ylidene-3,1(2H)-diylmethylene))dipyridine)-tris(acetonitrile)-iron bis(hexafluorophosphate) diethyl ether solvate

CCDC 1420290: Experimental Crystal Structure Determination : (6,6'-bis((3-methyl-2,3-dihydro-1H-imidazol-2-ylidene-1-yl)methyl)-2,2'-bipyridine)-bis(acetonitrile)-iron bis(hexafluorophosphate) acetonitrile solvate

CCDC 1420291: Experimental Crystal Structure Determination : (2-(3-((3-((3-methyl-2,3-dihydro-1H-imidazol-2-ylidene-1-yl)methyl)-2,3-dihydro-1H-imidazol-2-ylidene-1-yl)methyl)-2,3-dihydro-1H-imidazol-2-ylidene-1-yl)pyridine)-bis(acetonitrile)-iron bis(hexa

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