An Adaptable N‐Heterocyclic Carbene Macrocycle Hosting Copper in Three Oxidation States
Abstract
A neutral hybrid macrocycle with two trans-positioned N-heterocyclic carbenes (NHCs) and two pyridine donors hosts copper in three oxidation states (+I–+III) in a series of structurally characterized complexes (1–3). Redox interconversion of [LCu]+/2+/3+ is electrochemically (quasi)reversible and occurs at moderate potentials (E1/2=-0.45 V and +0.82 V (vs. Fc/Fc+)). A linear CNHC-Cu-CNHC arrangement and hemilability of the two pyridine donors allows the ligand to adapt to the different stereoelectronic and coordination requirements of CuI versus CuII/CuIII. Analytical methods such as NMR, UV/Vis, IR, electron paramagnetic resonance, and Cu Kβ high-energy-resolution fluorescence detection X-ray absorption spectroscopies, as well as DFT calculations, give insight into the geometric and electronic structures of the complexes. The XAS signatures of 1–3 are textbook examples for CuI, CuII, and CuIII species. Facile 2-electron interconversion combined with the exposure of two basic pyridine N sites in the reduced CuI form suggest that [LCu]+/2+/3+ may operate in catalysis via coupled 2 e-/2 H+ transfer.
- Authors:
-
[1];
[1];
[1]
- Institute of Inorganic Chemistry University of Göttingen Tammannstrasse 4 37077 Göttingen Germany
- Department of Inorganic Spectroscopy Max Planck Institute for Chemical Energy Conversion Stiftstrasse 34–36 45470 Mülheim an der Ruhr Germany
- Department of Chemistry & Catalysis Research Center Technische Universität München Lichtenbergstrasse 4 85748 Garching bei München Germany
- Publication Date:
- Research Org.:
- SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1605641
- Alternate Identifier(s):
- OSTI ID: 1605644; OSTI ID: 1623491
- Grant/Contract Number:
- AC02-76SF00515
- Resource Type:
- Published Article
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition) Journal Volume: 59 Journal Issue: 14; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- Germany
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; chemistry; copper(III); macrocyclic ligands; n-heterocyclic carbenes; oxidation states; x-ray absorption spectroscopy
Citation Formats
Liu, Yang, Resch, Stefan G., Klawitter, Iris, Cutsail, George E., Demeshko, Serhiy, Dechert, Sebastian, Kühn, Fritz E., DeBeer, Serena, and Meyer, Franc. An Adaptable N‐Heterocyclic Carbene Macrocycle Hosting Copper in Three Oxidation States. Germany: N. p., 2020.
Web. doi:10.1002/anie.201912745.
Liu, Yang, Resch, Stefan G., Klawitter, Iris, Cutsail, George E., Demeshko, Serhiy, Dechert, Sebastian, Kühn, Fritz E., DeBeer, Serena, & Meyer, Franc. An Adaptable N‐Heterocyclic Carbene Macrocycle Hosting Copper in Three Oxidation States. Germany. https://doi.org/10.1002/anie.201912745
Liu, Yang, Resch, Stefan G., Klawitter, Iris, Cutsail, George E., Demeshko, Serhiy, Dechert, Sebastian, Kühn, Fritz E., DeBeer, Serena, and Meyer, Franc. Fri .
"An Adaptable N‐Heterocyclic Carbene Macrocycle Hosting Copper in Three Oxidation States". Germany. https://doi.org/10.1002/anie.201912745.
@article{osti_1605641,
title = {An Adaptable N‐Heterocyclic Carbene Macrocycle Hosting Copper in Three Oxidation States},
author = {Liu, Yang and Resch, Stefan G. and Klawitter, Iris and Cutsail, George E. and Demeshko, Serhiy and Dechert, Sebastian and Kühn, Fritz E. and DeBeer, Serena and Meyer, Franc},
abstractNote = {A neutral hybrid macrocycle with two trans-positioned N-heterocyclic carbenes (NHCs) and two pyridine donors hosts copper in three oxidation states (+I–+III) in a series of structurally characterized complexes (1–3). Redox interconversion of [LCu]+/2+/3+ is electrochemically (quasi)reversible and occurs at moderate potentials (E1/2=-0.45 V and +0.82 V (vs. Fc/Fc+)). A linear CNHC-Cu-CNHC arrangement and hemilability of the two pyridine donors allows the ligand to adapt to the different stereoelectronic and coordination requirements of CuI versus CuII/CuIII. Analytical methods such as NMR, UV/Vis, IR, electron paramagnetic resonance, and Cu Kβ high-energy-resolution fluorescence detection X-ray absorption spectroscopies, as well as DFT calculations, give insight into the geometric and electronic structures of the complexes. The XAS signatures of 1–3 are textbook examples for CuI, CuII, and CuIII species. Facile 2-electron interconversion combined with the exposure of two basic pyridine N sites in the reduced CuI form suggest that [LCu]+/2+/3+ may operate in catalysis via coupled 2 e-/2 H+ transfer.},
doi = {10.1002/anie.201912745},
journal = {Angewandte Chemie (International Edition)},
number = 14,
volume = 59,
place = {Germany},
year = {Fri Jan 24 00:00:00 EST 2020},
month = {Fri Jan 24 00:00:00 EST 2020}
}
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Figure 1: Examples of previously reported organocopper(III) complexes.
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Die Vermeidung der Oxidationsstufe CuIII im Komplex [CuI(CF3)4]− durch Oxidation einer Trifluormethylgruppe
journal, January 1995
- Snyder, James P.
- Angewandte Chemie, Vol. 107, Issue 1
Synthesis and Structure of Surprisingly Stable Tetrakis(trifluoromethyl)cuprate(III) Salts
journal, October 1993
- Naumann, Dieter; Roy, Thomas; Tebbe, Karl-Friedrich
- Angewandte Chemie International Edition in English, Vol. 32, Issue 10
Copper(II) complexes of a heterotopic N- heterocyclic carbene ligand: Preparation and catalytic application
journal, March 2018
- Aaron Lin, Shih-Chieh; Liu, Yi-Hung; Peng, Shie-Ming
- Journal of Organometallic Chemistry, Vol. 859
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.