Unusual Stability of a Bacteriochlorin Electrocatalyst under Reductive Conditions. A Case Study on CO2 Conversion to CO

Jiang, Jianbing; Matula, Adam J.; Swierk, John R.; Romano, Neyen; Wu, Yueshen; Batista, Victor S.; Crabtree, Robert H.; Lindsey, Jonathan S.; Wang, Hailiang; Brudvig, Gary W.

doi:10.1021/acscatal.8b02991

Title: Unusual Stability of a Bacteriochlorin Electrocatalyst under Reductive Conditions. A Case Study on CO₂ Conversion to CO

Journal Article · Thu Sep 20 00:00:00 EDT 2018 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.8b02991· OSTI ID:1543706

Jiang, Jianbing ^[1]; Matula, Adam J. ^[1];

^[1]; Romano, Neyen ^[1]; Wu, Yueshen ^[1];

^[1];

^[2];

^[1];

^[1]

Yale Univ., New Haven, CT (United States). Dept. of Chemistry; Yale Univ., West Haven, CT (United States). Energy Sciences Inst.
North Carolina State Univ., Raleigh, NC (United States). Dept. of Chemistry

Photosynthetic CO₂ fixation is mediated by the enzyme RuBisCo, which employs a nonredox-active metal (Mg²⁺) to bind CO₂ adjacent to an organic ligand that provides reducing equivalents for CO₂ fixation. Attempts to use porphyrins as ligands in reductive catalysis have typically encountered severe stability issues owing to ligand reduction. Here, a synthetic zinc–bacteriochlorin is reported as an effective and robust electrocatalyst for CO₂ reduction to CO with an overpotential of 330 mV, without undergoing porphyrin-like ligand degradation (or demetalation) even after prolonged bulk electrolysis. The reaction has a CO Faradaic efficiency of 92% and sustains a total current density of 2.3 mA/cm² at -1.9 V vs Ag/AgCl. DFT calculations highlight the molecular origin of the observed stability and provide insights into catalytic steps. Here, this bioinspired study opens avenues for the application of bacteriochlorin compounds for reductive electrocatalysis with extended life beyond that seen with porphyrin counterparts.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC); Washington Univ., St. Louis, MO (United States); Yale Univ., New Haven, CT (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-05ER15661; FG02-07ER15909

OSTI ID:: 1543706

Journal Information:: ACS Catalysis, Vol. 8, Issue 11; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 20 works

Citation information provided by
Web of Science

References (41)

A Local Proton Source Enhances CO ₂ Electroreduction to CO by a Molecular Fe Catalyst Costentin, Cyrille; Drouet, Samuel; Robert, Marc Science, Vol. 338, Issue 6103 https://doi.org/10.1126/science.1224581	journal	October 2012
Efficient and selective molecular catalyst for the CO ₂ -to-CO electrochemical conversion in water Costentin, Cyrille; Robert, Marc; Savéant, Jean-Michel Proceedings of the National Academy of Sciences, Vol. 112, Issue 22 https://doi.org/10.1073/pnas.1507063112	journal	May 2015
Turnover Numbers, Turnover Frequencies, and Overpotential in Molecular Catalysis of Electrochemical Reactions. Cyclic Voltammetry and Preparative-Scale Electrolysis Costentin, Cyrille; Drouet, Samuel; Robert, Marc Journal of the American Chemical Society, Vol. 134, Issue 27, p. 11235-11242 https://doi.org/10.1021/ja303560c	journal	June 2012
Electrocatalytic reduction of carbon dioxide to carbon monoxide and methane at an immobilized cobalt protoporphyrin Shen, Jing; Kortlever, Ruud; Kas, Recep Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms9177	journal	September 2015
Fe-Porphyrin-Based Metal–Organic Framework Films as High-Surface Concentration, Heterogeneous Catalysts for Electrochemical Reduction of CO ₂ Hod, Idan; Sampson, Matthew D.; Deria, Pravas ACS Catalysis, Vol. 5, Issue 11 https://doi.org/10.1021/acscatal.5b01767	journal	September 2015
Water splitting–biosynthetic system with CO ₂ reduction efficiencies exceeding photosynthesis Liu, Chong; Colón, Brendan C.; Ziesack, Marika Science, Vol. 352, Issue 6290 https://doi.org/10.1126/science.aaf5039	journal	June 2016
Electrochemical CO ₂ Reduction to Hydrocarbons on a Heterogeneous Molecular Cu Catalyst in Aqueous Solution Weng, Zhe; Jiang, Jianbing; Wu, Yueshen Journal of the American Chemical Society, Vol. 138, Issue 26 https://doi.org/10.1021/jacs.6b04746	journal	June 2016
Enhanced Catalytic Activity of Cobalt Porphyrin in CO ₂ Electroreduction upon Immobilization on Carbon Materials Hu, Xin-Ming; Rønne, Magnus H.; Pedersen, Steen U. Angewandte Chemie International Edition, Vol. 56, Issue 23 https://doi.org/10.1002/anie.201701104	journal	May 2017
Electroreduction of CO ₂ Catalyzed by a Heterogenized Zn–Porphyrin Complex with a Redox-Innocent Metal Center Wu, Yueshen; Jiang, Jianbing; Weng, Zhe ACS Central Science, Vol. 3, Issue 8 https://doi.org/10.1021/acscentsci.7b00160	journal	July 2017
Efficient Visible-Light-Driven Carbon Dioxide Reduction by a Single-Atom Implanted Metal-Organic Framework Zhang, Huabin; Wei, Jing; Dong, Juncai Angewandte Chemie International Edition, Vol. 55, Issue 46 https://doi.org/10.1002/anie.201608597	journal	October 2016
Synthesis of meso -Substituted ABCD-Type Porphyrins by Functionalization Reactions Senge, Mathias O.; Shaker, Yasser M.; Pintea, Monica European Journal of Organic Chemistry, Vol. 2010, Issue 2 https://doi.org/10.1002/ejoc.200901113	journal	January 2010
Synthetic Routes to meso -Patterned Porphyrins Lindsey, Jonathan S. Accounts of Chemical Research, Vol. 43, Issue 2 https://doi.org/10.1021/ar900212t	journal	February 2010
Stirring the porphyrin alphabet soup—functionalization reactions for porphyrins Senge, Mathias O. Chemical Communications, Vol. 47, Issue 7 https://doi.org/10.1039/c0cc03984e	journal	January 2011
Post-Synthetic Modification of Porphyrin-Encapsulating Metal-Organic Materials by Cooperative Addition of Inorganic Salts to Enhance CO ₂ / CH ₄ Selectivity Zhang, Zhenjie; Gao, Wen-Yang; Wojtas, Lukasz Angewandte Chemie International Edition, Vol. 51, Issue 37 https://doi.org/10.1002/anie.201203594	journal	August 2012
Through-Space Charge Interaction Substituent Effects in Molecular Catalysis Leading to the Design of the Most Efficient Catalyst of CO ₂ -to-CO Electrochemical Conversion Azcarate, Iban; Costentin, Cyrille; Robert, Marc Journal of the American Chemical Society, Vol. 138, Issue 51 https://doi.org/10.1021/jacs.6b07014	journal	December 2016
Nickel phlorin intermediate formed by proton-coupled electron transfer in hydrogen evolution mechanism Solis, Brian H.; Maher, Andrew G.; Dogutan, Dilek K. Proceedings of the National Academy of Sciences, Vol. 113, Issue 3 https://doi.org/10.1073/pnas.1521834112	journal	December 2015
Stereoselective reduction, methylation, and phenylation of the 13-carbonyl group in chlorophyll derivatives Tamiaki, Hitoshi; Monobe, Rie; Koizumi, Shun Tetrahedron: Asymmetry, Vol. 24, Issue 15-16 https://doi.org/10.1016/j.tetasy.2013.06.010	journal	August 2013
Origin of the Regioselective Reduction of Chlorins Bruhn, Torsten; Brückner, Christian The Journal of Organic Chemistry, Vol. 80, Issue 10 https://doi.org/10.1021/acs.joc.5b00137	journal	March 2015
Comparison of rhenium–porphyrin dyads for CO ₂ photoreduction: photocatalytic studies and charge separation dynamics studied by time-resolved IR spectroscopy Windle, Christopher D.; George, Michael W.; Perutz, Robin N. Chemical Science, Vol. 6, Issue 12 https://doi.org/10.1039/C5SC02099A	journal	January 2015
Antimony Complexes for Electrocatalysis: Activity of a Main‐Group Element in Proton Reduction Jiang, Jianbing; Materna, Kelly L.; Hedström, Svante Angewandte Chemie International Edition, Vol. 56, Issue 31 https://doi.org/10.1002/anie.201704700	journal	July 2017
Mechanisms for CO Production from CO ₂ Using Reduced Rhenium Tricarbonyl Catalysts Agarwal, Jay; Fujita, Etsuko; Schaefer, Henry F. Journal of the American Chemical Society, Vol. 134, Issue 11 https://doi.org/10.1021/ja2105834	journal	March 2012
Solvent and substituent effects on UV-vis spectra and redox properties of zinc p-hydroxylphenylporphyrins Lu, Guifen; Jiang, Xiaoqin; Ou, Zhongping Journal of Porphyrins and Phthalocyanines, Vol. 21, Issue 07n08 https://doi.org/10.1142/S1088424617500456	journal	July 2017
Porphyrins as Photoredox Catalysts: Experimental and Theoretical Studies Rybicka-Jasińska, Katarzyna; Shan, Wenqian; Zawada, Katarzyna Journal of the American Chemical Society, Vol. 138, Issue 47 https://doi.org/10.1021/jacs.6b09036	journal	November 2016
Multiporphyrin Arrays with π–π Interchromophore Interactions Terazono, Yuichi; Kodis, Gerdenis; Chachisvilis, Mirianas Journal of the American Chemical Society, Vol. 137, Issue 1 https://doi.org/10.1021/ja510267c	journal	December 2014
Toward more efficient photochemical CO2 reduction: Use of scCO2 or photogenerated hydrides Doherty, Mark D.; Grills, David C.; Muckerman, James T. Coordination Chemistry Reviews, Vol. 254, Issue 21-22 https://doi.org/10.1016/j.ccr.2009.12.013	journal	November 2010
Separating Annihilation and Excitation Energy Transfer Dynamics in Light Harvesting Systems Vengris, Mikas; Larsen, Delmar S.; Valkunas, Leonas The Journal of Physical Chemistry B, Vol. 117, Issue 38 https://doi.org/10.1021/jp403301c	journal	April 2013
Expanded Scope of Synthetic Bacteriochlorins via Improved Acid Catalysis Conditions and Diverse Dihydrodipyrrin-Acetals Krayer, Michael; Ptaszek, Marcin; Kim, Han-Je The Journal of Organic Chemistry, Vol. 75, Issue 4, p. 1016-1039 https://doi.org/10.1021/jo9025572	journal	February 2010
Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures Reddy, Kanumuri Ramesh; Jiang, Jianbing; Krayer, Michael Chemical Science, Vol. 4, Issue 5 https://doi.org/10.1039/c3sc22317e	journal	January 2013
De Novo Synthesis of Stable Tetrahydroporphyrinic Macrocycles: Bacteriochlorins and a Tetradehydrocorrin Kim, Han-Je; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 70, Issue 14 https://doi.org/10.1021/jo050467y	journal	July 2005
Amphiphilic, hydrophilic, or hydrophobic synthetic bacteriochlorins in biohybrid light-harvesting architectures: consideration of molecular designs Jiang, Jianbing; Reddy, Kanumuri Ramesh; Pavan, M. Phani Photosynthesis Research, Vol. 122, Issue 2 https://doi.org/10.1007/s11120-014-0021-9	journal	July 2014
Near-infrared tunable bacteriochlorins equipped for bioorthogonal labeling Jiang, Jianbing; Taniguchi, Masahiko; Lindsey, Jonathan S. New Journal of Chemistry, Vol. 39, Issue 6 https://doi.org/10.1039/C5NJ00209E	journal	January 2015
Biohybrid Photosynthetic Antenna Complexes for Enhanced Light-Harvesting Springer, Joseph W.; Parkes-Loach, Pamela S.; Reddy, Kanumuri Ramesh Journal of the American Chemical Society, Vol. 134, Issue 10 https://doi.org/10.1021/ja207390y	journal	February 2012
In Vitro Photodynamic Therapy and Quantitative Structure−Activity Relationship Studies with Stable Synthetic Near-Infrared-Absorbing Bacteriochlorin Photosensitizers Huang, Ying-Ying; Mroz, Pawel; Zhiyentayev, Timur Journal of Medicinal Chemistry, Vol. 53, Issue 10 https://doi.org/10.1021/jm901908s	journal	May 2010
A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging Panchenko, Pavel A.; Grin, Mikhail A.; Fedorova, Olga A. Physical Chemistry Chemical Physics, Vol. 19, Issue 44 https://doi.org/10.1039/C7CP04449F	journal	January 2017
Activatable Organic Near-Infrared Fluorescent Probes Based on a Bacteriochlorin Platform: Synthesis and Multicolor in Vivo Imaging with a Single Excitation Harada, Toshiko; Sano, Kohei; Sato, Kazuhide Bioconjugate Chemistry, Vol. 25, Issue 2 https://doi.org/10.1021/bc4005238	journal	January 2014
Synthesis and Physicochemical Properties of Metallobacteriochlorins Chen, Chih-Yuan; Sun, Erjun; Fan, Dazhong Inorganic Chemistry, Vol. 51, Issue 17 https://doi.org/10.1021/ic301262k	journal	August 2012
Reduction of Systematic Uncertainty in DFT Redox Potentials of Transition-Metal Complexes Konezny, Steven J.; Doherty, Mark D.; Luca, Oana R. The Journal of Physical Chemistry C, Vol. 116, Issue 10 https://doi.org/10.1021/jp300485t	journal	March 2012
Ruthenium complexes with non-innocent ligands: Electron distribution and implications for catalysis Boyer, Julie L.; Rochford, Jonathan; Tsai, Ming-Kang Coordination Chemistry Reviews, Vol. 254, Issue 3-4 https://doi.org/10.1016/j.ccr.2009.09.006	journal	February 2010
Theoretical studies of the mechanism of catalytic hydrogen production by a cobaloxime Muckerman, James T.; Fujita, Etsuko Chemical Communications, Vol. 47, Issue 46 https://doi.org/10.1039/c1cc15330g	journal	January 2011
Spectra of porphyrins Gouterman, Martin; Wagnière, Georges H.; Snyder, Lawrence C. Journal of Molecular Spectroscopy, Vol. 11, Issue 1-6 https://doi.org/10.1016/0022-2852(63)90011-0	journal	January 1963
De Novo Synthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World Lindsey, Jonathan S. Chemical Reviews, Vol. 115, Issue 13 https://doi.org/10.1021/acs.chemrev.5b00065	journal	June 2015

Cited By (3)

A bacteriochlorin-diketopyrrolopyrrole triad as a donor for solution-processed bulk heterojunction organic solar cells Ponsot, Flavien; Bucher, Léo; Desbois, Nicolas Journal of Materials Chemistry C, Vol. 7, Issue 31 https://doi.org/10.1039/c9tc02724f	journal	January 2019
Heterogeneous molecular catalysts for electrocatalytic CO2 reduction Corbin, Nathan; Zeng, Joy; Williams, Kindle Nano Research, Vol. 12, Issue 9 https://doi.org/10.1007/s12274-019-2403-y	journal	May 2019
A new polypyridyl‐based Ru (II) complex as a highly efficient electrocatalyst for CO ₂ reduction Daryanavard, Marzieh; Masoumpour, Marziyeh Sadat Applied Organometallic Chemistry, Vol. 34, Issue 3 https://doi.org/10.1002/aoc.5389	journal	January 2020

Figures / Tables (6)

Similar Records

Electroreduction of CO ₂ Catalyzed by a Heterogenized Zn–Porphyrin Complex with a Redox-Innocent Metal Center

Journal Article · Wed Jul 26 00:00:00 EDT 2017 · ACS Central Science · OSTI ID:1543706

Wu, Yueshen; Jiang, Jianbing; Weng, Zhe; +6 more

Electroreduction of CO ₂ Catalyzed by a Heterogenized Zn–Porphyrin Complex with a Redox-Innocent Metal Center

Journal Article · Wed Jul 26 00:00:00 EDT 2017 · ACS Central Science · OSTI ID:1543706

Wu, Yueshen; Jiang, Jianbing; Weng, Zhe; +6 more

Investigation of a bacteriochlorin-containing pentad array for panchromatic light-harvesting and charge separation

Journal Article · Wed Jan 04 00:00:00 EST 2023 · Physical Chemistry Chemical Physics. PCCP · OSTI ID:1543706

Jing, Haoyu; Magdaong, Nikki Cecil M.; Diers, James R.; +4 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
chemistry
bacteriochlorin
Co2 conversion
electrocatalysis
hydrogenation
porphyrin

Title: Unusual Stability of a Bacteriochlorin Electrocatalyst under Reductive Conditions. A Case Study on CO2 Conversion to CO

Citation Formats