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Title: Positional effects of second-sphere amide pendants on electrochemical CO 2 reduction catalyzed by iron porphyrins

Abstract

The development of catalysts for electrochemical reduction of carbon dioxide offers an attractive approach to transforming this greenhouse gas into value-added carbon products with sustainable energy input. Inspired by natural bioinorganic systems that feature precisely positioned hydrogen-bond donors in the secondary coordination sphere to direct chemical transformations occurring at redox-active metal centers, we now report the design, synthesis, and characterization of a series of iron tetraphenylporphyrin (Fe-TPP) derivatives bearing amide pendants at various positions at the periphery of the metal core. Proper positioning of the amide pendants greatly affects the electrocatalytic activity for carbon dioxide reduction to carbon monoxide. In particular, derivatives bearing proximal and distal amide pendants on the ortho position of the phenyl ring exhibit significantly larger turnover frequencies (TOF) compared to the analogous para-functionalized amide isomers or unfunctionalized Fe-TPP. Analysis of TOF as a function of catalyst standard reduction potential enables first-sphere electronic effects to be disentangled from second-sphere through-space interactions, suggesting that the ortho-functionalized porphyrins can utilize the latter second-sphere property to promote CO2 reduction. Indeed, the distally-functionalized ortho-amide isomer shows a significantly larger through-space interaction than its proximal ortho-amide analogue. These data establish that proper positioning of secondary coordination sphere groups is an effective designmore » element for breaking electronic scaling relationships that are often observed in electrochemical CO2 reduction.The development of catalysts for electrochemical reduction of carbon dioxide offers an attractive approach to transforming this greenhouse gas into value-added carbon products with sustainable energy input.« less

Authors:
 [1];  [1];  [2];  [1]; ORCiD logo [1]
  1. Department of Chemistry, University of California, Berkeley, USA, Chemical Sciences Division
  2. Department of Chemistry, University of California, Berkeley, USA
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1422003
Alternate Identifier(s):
OSTI ID: 1465425
Grant/Contract Number:  
101528-002; AC02-05CH11231
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 9 Journal Issue: 11; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Nichols, Eva M., Derrick, Jeffrey S., Nistanaki, Sepand K., Smith, Peter T., and Chang, Christopher J. Positional effects of second-sphere amide pendants on electrochemical CO 2 reduction catalyzed by iron porphyrins. United Kingdom: N. p., 2018. Web. doi:10.1039/C7SC04682K.
Nichols, Eva M., Derrick, Jeffrey S., Nistanaki, Sepand K., Smith, Peter T., & Chang, Christopher J. Positional effects of second-sphere amide pendants on electrochemical CO 2 reduction catalyzed by iron porphyrins. United Kingdom. https://doi.org/10.1039/C7SC04682K
Nichols, Eva M., Derrick, Jeffrey S., Nistanaki, Sepand K., Smith, Peter T., and Chang, Christopher J. Mon . "Positional effects of second-sphere amide pendants on electrochemical CO 2 reduction catalyzed by iron porphyrins". United Kingdom. https://doi.org/10.1039/C7SC04682K.
@article{osti_1422003,
title = {Positional effects of second-sphere amide pendants on electrochemical CO 2 reduction catalyzed by iron porphyrins},
author = {Nichols, Eva M. and Derrick, Jeffrey S. and Nistanaki, Sepand K. and Smith, Peter T. and Chang, Christopher J.},
abstractNote = {The development of catalysts for electrochemical reduction of carbon dioxide offers an attractive approach to transforming this greenhouse gas into value-added carbon products with sustainable energy input. Inspired by natural bioinorganic systems that feature precisely positioned hydrogen-bond donors in the secondary coordination sphere to direct chemical transformations occurring at redox-active metal centers, we now report the design, synthesis, and characterization of a series of iron tetraphenylporphyrin (Fe-TPP) derivatives bearing amide pendants at various positions at the periphery of the metal core. Proper positioning of the amide pendants greatly affects the electrocatalytic activity for carbon dioxide reduction to carbon monoxide. In particular, derivatives bearing proximal and distal amide pendants on the ortho position of the phenyl ring exhibit significantly larger turnover frequencies (TOF) compared to the analogous para-functionalized amide isomers or unfunctionalized Fe-TPP. Analysis of TOF as a function of catalyst standard reduction potential enables first-sphere electronic effects to be disentangled from second-sphere through-space interactions, suggesting that the ortho-functionalized porphyrins can utilize the latter second-sphere property to promote CO2 reduction. Indeed, the distally-functionalized ortho-amide isomer shows a significantly larger through-space interaction than its proximal ortho-amide analogue. These data establish that proper positioning of secondary coordination sphere groups is an effective design element for breaking electronic scaling relationships that are often observed in electrochemical CO2 reduction.The development of catalysts for electrochemical reduction of carbon dioxide offers an attractive approach to transforming this greenhouse gas into value-added carbon products with sustainable energy input.},
doi = {10.1039/C7SC04682K},
journal = {Chemical Science},
number = 11,
volume = 9,
place = {United Kingdom},
year = {2018},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1039/C7SC04682K

Citation Metrics:
Cited by: 12 works
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Figures / Tables:

Fig. 1 Fig. 1: Titration of 3,5-[bis(trifluoromethyl)phenyl]amide to Fe-TPP under CO2 showing current increases with increasing concentrations of amide. Conditions: 0.1 M TBAPF6 in DMF, 1 mM Fe-TPP.

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Works referencing / citing this record:

Structural and Spectroscopic Characterization of a Mononuclear Hydroperoxo-Copper(II) Complex with Tripodal Pyridylamine Ligands
journal, April 1998


[Mn(bipyridyl)(CO)3Br]: An Abundant Metal Carbonyl Complex as Efficient Electrocatalyst for CO2 Reduction
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Bio-inspired mechanistic insights into CO2 reduction
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Molecular Designs for Controlling the Local Environments around Metal Ions
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Activating Fe(I) Porphyrins for the Hydrogen Evolution Reaction Using Second-Sphere Proton Transfer Residues
journal, February 2017


Dissection of Electronic Substituent Effects in Multielectron–Multistep Molecular Catalysis. Electrochemical CO 2 -to-CO Conversion Catalyzed by Iron Porphyrins
journal, December 2016

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Homogenous Electrocatalytic Oxygen Reduction Rates Correlate with Reaction Overpotential in Acidic Organic Solutions
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journal, December 2009

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Frontiers, Opportunities, and Challenges in Biochemical and Chemical Catalysis of CO 2 Fixation
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Electrocatalytic reduction of carbon dioxide by 2,2'-bipyridine complexes of rhodium and iridium
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Modeling Substrate- and Inhibitor-Bound Forms of Liver Alcohol Dehydrogenase:  Chemistry of Mononuclear Nitrogen/Sulfur-Ligated Zinc Alcohol, Formamide, and Sulfoxide Complexes
journal, September 2002

  • Makowska-Grzyska, Magdalena M.; Jeppson, Peter C.; Allred, Russell A.
  • Inorganic Chemistry, Vol. 41, Issue 19
  • DOI: 10.1021/ic0255609

Steric and Hydrogen-Bonding Effects on the Stability of Copper Complexes with Small Molecules
journal, September 2004

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  • Inorganic Chemistry, Vol. 43, Issue 18
  • DOI: 10.1021/ic0496572

Studies of Cobalt-Mediated Electrocatalytic CO 2 Reduction Using a Redox-Active Ligand
journal, April 2014

  • Lacy, David C.; McCrory, Charles C. L.; Peters, Jonas C.
  • Inorganic Chemistry, Vol. 53, Issue 10
  • DOI: 10.1021/ic403122j

Role of the Secondary Coordination Sphere in Metal-Mediated Dioxygen Activation
journal, April 2010

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