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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]
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  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 Laboratory (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.
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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
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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.
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@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 = {Mon Jan 01 00:00:00 EST 2018},
month = {Mon Jan 01 00:00:00 EST 2018}
}
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Journal Article:
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https://doi.org/10.1039/C7SC04682K
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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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