Synergistic Porosity and Charge Effects in a Supramolecular Porphyrin Cage Promote Efficient Photocatalytic CO2 Reduction**

An, Lun; De La Torre, Patricia; Smith, Peter T.; Narouz, Mina R.; Chang, Christopher J.

doi:10.1002/anie.202209396

Title: Synergistic Porosity and Charge Effects in a Supramolecular Porphyrin Cage Promote Efficient Photocatalytic CO₂ Reduction**

Journal Article · Tue Dec 20 00:00:00 EST 2022 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.202209396· OSTI ID:2246868

^[1]; De La Torre, Patricia ^[1];

^[1];

^[1]

Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Abstract We present a supramolecular approach to catalyzing photochemical CO ₂ reduction through second‐sphere porosity and charge effects. An iron porphyrin box ( PB ) bearing 24 cationic groups, FePB‐2(P) , was made via post‐synthetic modification of an alkyne‐functionalized supramolecular synthon. FePB‐2(P) promotes the photochemical CO ₂ reduction reaction (CO ₂ RR) with 97 % selectivity for CO product, achieving turnover numbers (TON) exceeding 7000 and initial turnover frequencies (TOF _max ) reaching 1400 min ⁻¹ . The cooperativity between porosity and charge results in a 41‐fold increase in activity relative to the parent Fe tetraphenylporphyrin ( FeTPP ) catalyst, which is far greater than analogs that augment catalysis through porosity ( FePB‐3(N ), 4‐fold increase) or charge (Fe p ‐tetramethylanilinium porphyrin ( Fe‐ p ‐TMA ), 6‐fold increase) alone. This work establishes that synergistic pendants in the secondary coordination sphere can be leveraged as a design element to augment catalysis at primary active sites within confined spaces.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB); USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR); National Institutes of Health (NIH)

Grant/Contract Number:: AC02-05CH11231; S10OD024998

OSTI ID:: 2246868

Alternate ID(s):: OSTI ID: 1905941

Journal Information:: Angewandte Chemie (International Edition), Vol. 62, Issue 5; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (127)

Atropisomeric Hydrogen Bonding Control for CO ₂ Binding and Enhancement of Electrocatalytic Reduction at Iron Porphyrins Gotico, Philipp; Roupnel, Loïc; Guillot, Regis Angewandte Chemie International Edition, Vol. 59, Issue 50 https://doi.org/10.1002/anie.202010859	journal	October 2020
Tuning Second Coordination Sphere Interactions in Polypyridyl–Iron Complexes to Achieve Selective Electrocatalytic Reduction of Carbon Dioxide to Carbon Monoxide Zee, David Z.; Nippe, Michael; King, Amanda E. Inorganic Chemistry, Vol. 59, Issue 7 https://doi.org/10.1021/acs.inorgchem.0c00455	journal	March 2020
Computational Study of an Iron(II) Polypyridine Electrocatalyst for CO ₂ Reduction: Key Roles for Intramolecular Interactions in CO ₂ Binding and Proton Transfer Loipersberger, Matthias; Zee, David Z.; Panetier, Julien A. Inorganic Chemistry, Vol. 59, Issue 12 https://doi.org/10.1021/acs.inorgchem.0c00454	journal	May 2020
Exchange Coupling Determines Metal-Dependent Efficiency for Iron- and Cobalt-Catalyzed Photochemical CO₂ Reduction De La Torre, Patricia; Derrick, Jeffrey S.; Snider, Andrew ACS Catalysis, Vol. 12, Issue 14 https://doi.org/10.1021/acscatal.2c02072	journal	July 2022
Beyond Platonic: How to Build Metal–Organic Polyhedra Capable of Binding Low-Symmetry, Information-Rich Molecular Cargoes McTernan, Charlie T.; Davies, Jack A.; Nitschke, Jonathan R. Chemical Reviews, Vol. 122, Issue 11 https://doi.org/10.1021/acs.chemrev.1c00763	journal	April 2022
Design and Applications of Water-Soluble Coordination Cages Percástegui, Edmundo G.; Ronson, Tanya K.; Nitschke, Jonathan R. Chemical Reviews, Vol. 120, Issue 24 https://doi.org/10.1021/acs.chemrev.0c00672	journal	November 2020
Electrochemical CO₂ Reduction on Metal Electrodes Hori, Y.; Vayenas, Constantinos G.; White, Ralph E. Modern Aspects of Electrochemistry, p. 89-189 https://doi.org/10.1007/978-0-387-49489-0_3	book	January 2008
Visible-Light-Driven Conversion of CO ₂ to CH ₄ with an Organic Sensitizer and an Iron Porphyrin Catalyst Rao, Heng; Lim, Chern-Hooi; Bonin, Julien Journal of the American Chemical Society, Vol. 140, Issue 51 https://doi.org/10.1021/jacs.8b09740	journal	December 2018
Porphyrin Boxes Mukhopadhyay, Rahul Dev; Kim, Younghoon; Koo, Jaehyoung Accounts of Chemical Research, Vol. 51, Issue 11 https://doi.org/10.1021/acs.accounts.8b00302	journal	October 2018
Retikuläre Chemie metall‐organischer Polyeder Tranchemontagne, David J.; Ni, Zheng; O'Keeffe, Michael Angewandte Chemie, Vol. 120, Issue 28 https://doi.org/10.1002/ange.200705008	journal	June 2008
Permanently Microporous Metal–Organic Polyhedra Gosselin, Eric J.; Rowland, Casey A.; Bloch, Eric D. Chemical Reviews, Vol. 120, Issue 16 https://doi.org/10.1021/acs.chemrev.9b00803	journal	June 2020
Organic cage compounds – from shape-persistency to function Zhang, Gang; Mastalerz, Michael Chem. Soc. Rev., Vol. 43, Issue 6 https://doi.org/10.1039/C3CS60358J	journal	January 2014
A Stable and Conductive Metallophthalocyanine Framework for Electrocatalytic Carbon Dioxide Reduction in Water Huang, Ning; Lee, Ka Hung; Yue, Yan Angewandte Chemie International Edition, Vol. 59, Issue 38 https://doi.org/10.1002/anie.202005274	journal	July 2020
Quick and Easy Method to Dramatically Improve the Electrochemical CO ₂ Reduction Activity of an Iron Porphyrin Complex Kosugi, Kento; Kondo, Mio; Masaoka, Shigeyuki Angewandte Chemie International Edition, Vol. 60, Issue 40 https://doi.org/10.1002/anie.202110190	journal	August 2021
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
Atomically Dispersed Metal Sites in MOF-Based Materials for Electrocatalytic and Photocatalytic Energy Conversion Liang, Zibin; Qu, Chong; Xia, Dingguo Angewandte Chemie International Edition, Vol. 57, Issue 31 https://doi.org/10.1002/anie.201800269	journal	June 2018
Metal–Organic Frameworks and Self-Assembled Supramolecular Coordination Complexes: Comparing and Contrasting the Design, Synthesis, and Functionality of Metal–Organic Materials Cook, Timothy R.; Zheng, Yao-Rong; Stang, Peter J. Chemical Reviews, Vol. 113, Issue 1 https://doi.org/10.1021/cr3002824	journal	November 2012
Porphyrin Boxes: Rationally Designed Porous Organic Cages Hong, Soonsang; Rohman, Md. Rumum; Jia, Jiangtao Angewandte Chemie International Edition, Vol. 54, Issue 45 https://doi.org/10.1002/anie.201505531	journal	August 2015
Transition metal catalysis in confined spaces Leenders, Stefan H. A. M.; Gramage-Doria, Rafael; de Bruin, Bas Chemical Society Reviews, Vol. 44, Issue 2 https://doi.org/10.1039/C4CS00192C	journal	January 2015
Facile Solvent-Free Synthesis of Thin Iron Porphyrin COFs on Carbon Cloth Electrodes for CO ₂ Reduction Cheung, Po Ling; Lee, Sze Koon; Kubiak, Clifford P. Chemistry of Materials, Vol. 31, Issue 6 https://doi.org/10.1021/acs.chemmater.8b04370	journal	June 2018
Mediated Inner‐Sphere Electron Transfer Induces Homogeneous Reduction of CO ₂ via Through‐Space Electronic Conjugation** Hooe, Shelby L.; Moreno, Juan J.; Reid, Amelia G. Angewandte Chemie International Edition, Vol. 61, Issue 1 https://doi.org/10.1002/anie.202109645	journal	November 2021
Activating a Low Overpotential CO ₂ Reduction Mechanism by a Strategic Ligand Modification on a Ruthenium Polypyridyl Catalyst Johnson, Ben A.; Maji, Somnath; Agarwala, Hemlata Angewandte Chemie International Edition, Vol. 55, Issue 5 https://doi.org/10.1002/anie.201508490	journal	December 2015
Controlling the Oxygen Reduction Selectivity of Asymmetric Cobalt Porphyrins by Using Local Electrostatic Interactions Zhang, Rui; Warren, Jeffrey J. Journal of the American Chemical Society, Vol. 142, Issue 31 https://doi.org/10.1021/jacs.0c03861	journal	July 2020
Second‐Sphere Biomimetic Multipoint Hydrogen‐Bonding Patterns to Boost CO ₂ Reduction of Iron Porphyrins Gotico, Philipp; Boitrel, Bernard; Guillot, Régis Angewandte Chemie, Vol. 131, Issue 14 https://doi.org/10.1002/ange.201814339	journal	February 2019
Supramolecular Tuning Enables Selective Oxygen Reduction Catalyzed by Cobalt Porphyrins for Direct Electrosynthesis of Hydrogen Peroxide Smith, Peter T.; Kim, Younghoon; Benke, Bahiru Punja Angewandte Chemie, Vol. 132, Issue 12 https://doi.org/10.1002/ange.201916131	journal	January 2020
Uniting biological and chemical strategies for selective CO2 reduction Shafaat, Hannah S.; Yang, Jenny Y. Nature Catalysis, Vol. 4, Issue 11 https://doi.org/10.1038/s41929-021-00683-1	journal	November 2021
Mediated Inner‐Sphere Electron Transfer Induces Homogeneous Reduction of CO₂ via Through‐Space Electronic Conjugation** Hooe, Shelby L.; Moreno, Juan J.; Reid, Amelia G. Angewandte Chemie, Vol. 134, Issue 1 https://doi.org/10.1002/ange.202109645	journal	November 2021
A Thiourea Tether in the Second Coordination Sphere as a Binding Site for CO ₂ and a Proton Donor Promotes the Electrochemical Reduction of CO ₂ to CO Catalyzed by a Rhenium Bipyridine-Type Complex Haviv, Eynat; Azaiza-Dabbah, Dima; Carmieli, Raanan Journal of the American Chemical Society, Vol. 140, Issue 39 https://doi.org/10.1021/jacs.8b05658	journal	September 2018
Visible-light-driven methane formation from CO2 with a molecular iron catalyst Rao, Heng; Schmidt, Luciana C.; Bonin, Julien Nature, Vol. 548, Issue 7665 https://doi.org/10.1038/nature23016	journal	July 2017
Molecular containers Ballester, Pablo; Fujita, Makoto; Rebek, Julius Chemical Society Reviews, Vol. 44, Issue 2 https://doi.org/10.1039/C4CS90101K	journal	January 2015
The chemistry of metal–organic frameworks for CO2 capture, regeneration and conversion Trickett, Christopher A.; Helal, Aasif; Al-Maythalony, Bassem A. Nature Reviews Materials, Vol. 2, Issue 8 https://doi.org/10.1038/natrevmats.2017.45	journal	July 2017
Dissection of Light‐Induced Charge Accumulation at a Highly Active Iron Porphyrin: Insights in the Photocatalytic CO ₂ Reduction Pugliese, Eva; Gotico, Philipp; Wehrung, Iris Angewandte Chemie International Edition, Vol. 61, Issue 14 https://doi.org/10.1002/anie.202117530	journal	February 2022
Covalent organic frameworks comprising cobalt porphyrins for catalytic CO ₂ reduction in water Lin, Song; Diercks, Christian S.; Zhang, Yue-Biao Science, Vol. 349, Issue 6253 https://doi.org/10.1126/science.aac8343	journal	August 2015
Progress and Perspectives of Electrochemical CO ₂ Reduction on Copper in Aqueous Electrolyte Nitopi, Stephanie; Bertheussen, Erlend; Scott, Soren B. Chemical Reviews, Vol. 119, Issue 12 https://doi.org/10.1021/acs.chemrev.8b00705	journal	April 2019
Enhancing a Molecular Electrocatalyst’s Activity for CO ₂ Reduction by Simultaneously Modulating Three Substituent Effects Nie, Weixuan; Tarnopol, Drew E.; McCrory, Charles C. L. Journal of the American Chemical Society, Vol. 143, Issue 10 https://doi.org/10.1021/jacs.0c09357	journal	March 2021
Pendant Hydrogen-Bond Donors in Cobalt Catalysts Independently Enhance CO ₂ Reduction Chapovetsky, Alon; Welborn, Matthew; Luna, John M. ACS Central Science, Vol. 4, Issue 3 https://doi.org/10.1021/acscentsci.7b00607	journal	February 2018
A Stable and Conductive Metallophthalocyanine Framework for Electrocatalytic Carbon Dioxide Reduction in Water Huang, Ning; Lee, Ka Hung; Yue, Yan Angewandte Chemie, Vol. 132, Issue 38 https://doi.org/10.1002/ange.202005274	journal	July 2020
Covalent Organic Framework Based Functional Materials: Important Catalysts for Efficient CO ₂ Utilization Lu, Meng; Zhang, Mi; Liu, Jiang Angewandte Chemie International Edition, Vol. 61, Issue 15 https://doi.org/10.1002/anie.202200003	journal	February 2022
An Iron Pyridyl-Carbene Electrocatalyst for Low Overpotential CO ₂ Reduction to CO Gonell, Sergio; Lloret-Fillol, Julio; Miller, Alexander J. M. ACS Catalysis, Vol. 11, Issue 2 https://doi.org/10.1021/acscatal.0c03798	journal	December 2020
Funktionale molekulare Reaktionskolben: neuartige Eigenschaften und Reaktionen in diskreten, selbstorganisierten Wirtmolekülen Yoshizawa, Michito; Klosterman, Jeremy K.; Fujita, Makoto Angewandte Chemie, Vol. 121, Issue 19 https://doi.org/10.1002/ange.200805340	journal	April 2009
Activating the Fe(I) State of Iron Porphyrinoid with Second-Sphere Proton Transfer Residues for Selective Reduction of CO ₂ to HCOOH via Fe(III/II)–COOH Intermediate(s) Amanullah, Sk; Saha, Paramita; Dey, Abhishek Journal of the American Chemical Society, Vol. 143, Issue 34 https://doi.org/10.1021/jacs.1c04392	journal	August 2021
A Supramolecular Porous Organic Cage Platform Promotes Electrochemical Hydrogen Evolution from Water Catalyzed by Cobalt Porphyrins Smith, Peter T.; Benke, Bahiru Punja; An, Lun ChemElectroChem, Vol. 8, Issue 9 https://doi.org/10.1002/celc.202100331	journal	May 2021
Boosting Electrochemical CO ₂ Reduction on Metal–Organic Frameworks via Ligand Doping Dou, Shuo; Song, Jiajia; Xi, Shibo Angewandte Chemie, Vol. 131, Issue 12 https://doi.org/10.1002/ange.201814711	journal	February 2019
Molecular catalysis of CO ₂ reduction: recent advances and perspectives in electrochemical and light-driven processes with selected Fe, Ni and Co aza macrocyclic and polypyridine complexes Boutin, E.; Merakeb, L.; Ma, B. Chemical Society Reviews, Vol. 49, Issue 16 https://doi.org/10.1039/D0CS00218F	journal	January 2020
Hybrid Catalysts for Artificial Photosynthesis: Merging Approaches from Molecular, Materials, and Biological Catalysis Smith, Peter T.; Nichols, Eva M.; Cao, Zhi Accounts of Chemical Research, Vol. 53, Issue 3 https://doi.org/10.1021/acs.accounts.9b00619	journal	March 2020
A stable covalent organic framework for photocatalytic carbon dioxide reduction Fu, Zhiwei; Wang, Xiaoyan; Gardner, Adrian M. Chemical Science, Vol. 11, Issue 2 https://doi.org/10.1039/C9SC03800K	journal	January 2020
Homogeneously Catalyzed Electroreduction of Carbon Dioxide—Methods, Mechanisms, and Catalysts Francke, Robert; Schille, Benjamin; Roemelt, Michael Chemical Reviews, Vol. 118, Issue 9 https://doi.org/10.1021/acs.chemrev.7b00459	journal	January 2018
Selectivity in Electrochemical CO ₂ Reduction Saha, Paramita; Amanullah, Sk; Dey, Abhishek Accounts of Chemical Research, Vol. 55, Issue 2 https://doi.org/10.1021/acs.accounts.1c00678	journal	January 2022
Regulating Photocatalysis by Spin-State Manipulation of Cobalt in Covalent Organic Frameworks Gong, Yun-Nan; Zhong, Wenhui; Li, Yang Journal of the American Chemical Society, Vol. 142, Issue 39 https://doi.org/10.1021/jacs.0c07206	journal	September 2020
A local hydrophobic environment in a metal–organic framework for boosting photocatalytic CO ₂ reduction in the presence of water Huang, Ning-Yu; Zhang, Xue-Wen; Xu, Yu-Zhi Chemical Communications, Vol. 55, Issue 98 https://doi.org/10.1039/C9CC08094E	journal	January 2019
Functional Molecular Flasks: New Properties and Reactions within Discrete, Self-Assembled Hosts Yoshizawa, Michito; Klosterman, Jeremy K.; Fujita, Makoto Angewandte Chemie International Edition, Vol. 48, Issue 19, p. 3418-3438 https://doi.org/10.1002/anie.200805340	journal	April 2009
Metal–Organic Frameworks as Platform Materials for Solar Fuels Catalysis Majewski, Marek B.; Peters, Aaron W.; Wasielewski, Michael R. ACS Energy Letters, Vol. 3, Issue 3 https://doi.org/10.1021/acsenergylett.8b00010	journal	February 2018
Boosting Electrochemical CO ₂ Reduction on Metal–Organic Frameworks via Ligand Doping Dou, Shuo; Song, Jiajia; Xi, Shibo Angewandte Chemie International Edition, Vol. 58, Issue 12 https://doi.org/10.1002/anie.201814711	journal	March 2019
Supramolecular Porphyrin Cages Assembled at Molecular–Materials Interfaces for Electrocatalytic CO Reduction Gong, Ming; Cao, Zhi; Liu, Wei ACS Central Science, Vol. 3, Issue 9 https://doi.org/10.1021/acscentsci.7b00316	journal	September 2017
Porous Shape-Persistent Organic Cage Compounds of Different Size, Geometry, and Function Mastalerz, Michael Accounts of Chemical Research, Vol. 51, Issue 10 https://doi.org/10.1021/acs.accounts.8b00298	journal	September 2018
Reticular Chemistry of Metal–Organic Polyhedra Tranchemontagne, David J.; Ni, Zheng; O'Keeffe, Michael Angewandte Chemie International Edition, Vol. 47, Issue 28, p. 5136-5147 https://doi.org/10.1002/anie.200705008	journal	June 2008
Inhibiting the Hydrogen Evolution Reaction (HER) with Proximal Cations: A Strategy for Promoting Selective Electrocatalytic Reduction Barlow, Jeffrey M.; Ziller, Joseph W.; Yang, Jenny Y. ACS Catalysis, Vol. 11, Issue 13 https://doi.org/10.1021/acscatal.1c01527	journal	June 2021
A Highly Efficient Method for the Reductive Etherification of Carbonyl Compounds with Triethylsilane and Alkoxytrimethylsilane Catalyzed by Iron(III) Chloride Oriyama, Takeshi; Iwanami, Katsuyuki; Seo, Hana Synthesis, Vol. 2005, Issue 02 https://doi.org/10.1055/s-2004-834942	journal	January 2005
Photochemistry Meets Porous Organic Cages Huang, Hsin-Hua; Šolomek, Tomáš CHIMIA, Vol. 75, Issue 4 https://doi.org/10.2533/chimia.2021.285	journal	April 2021
Utilization of Low-Concentration CO₂ with Molecular Catalysts Assisted by CO₂-Capturing Ability of Catalysts, Additives, or Reaction Media Yamazaki, Yasuomi; Miyaji, Masahiko; Ishitani, Osamu Journal of the American Chemical Society, Vol. 144, Issue 15 https://doi.org/10.1021/jacs.2c02245	journal	April 2022
Photocatalytic Reduction of Low Concentration of CO ₂ Nakajima, Takuya; Tamaki, Yusuke; Ueno, Kazuki Journal of the American Chemical Society, Vol. 138, Issue 42 https://doi.org/10.1021/jacs.6b08824	journal	October 2016
Metal–Organic Frameworks for Electrocatalytic Reduction of Carbon Dioxide Kornienko, Nikolay; Zhao, Yingbo; Kley, Christopher S. Journal of the American Chemical Society, Vol. 137, Issue 44 https://doi.org/10.1021/jacs.5b08212	journal	October 2015
Iron Porphyrins Embedded into a Supramolecular Porous Organic Cage for Electrochemical CO 2 Reduction in Water Smith, Peter T.; Benke, Bahiru Punja; Cao, Zhi Angewandte Chemie, Vol. 130, Issue 31 https://doi.org/10.1002/ange.201803873	journal	July 2018
Powering the planet: Chemical challenges in solar energy utilization Lewis, N. S.; Nocera, D. G. Proceedings of the National Academy of Sciences, Vol. 103, Issue 43, p. 15729-15735 https://doi.org/10.1073/pnas.0603395103	journal	October 2006
Porous organic cages: soluble, modular and molecular pores Hasell, Tom; Cooper, Andrew I. Nature Reviews Materials, Vol. 1, Issue 9 https://doi.org/10.1038/natrevmats.2016.53	journal	July 2016
Oriented electron transmission in polyoxometalate-metalloporphyrin organic framework for highly selective electroreduction of CO2 Wang, Yi-Rong; Huang, Qing; He, Chun-Ting Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-06938-z	journal	October 2018
Highly Selective CO₂ Electroreduction to C₂H₄ Using a Metal–Organic Framework with Dual Active Sites Qiu, Xiao-Feng; Zhu, Hao-Lin; Huang, Jia-Run Journal of the American Chemical Society, Vol. 143, Issue 19 https://doi.org/10.1021/jacs.1c01466	journal	May 2021
What would it take for renewably powered electrosynthesis to displace petrochemical processes? De Luna, Phil; Hahn, Christopher; Higgins, Drew Science, Vol. 364, Issue 6438 https://doi.org/10.1126/science.aav3506	journal	April 2019
Electrocatalytic CO ₂ Reduction to Formate with Molecular Fe(III) Complexes Containing Pendent Proton Relays Nichols, Asa W.; Hooe, Shelby L.; Kuehner, Joseph S. Inorganic Chemistry, Vol. 59, Issue 9 https://doi.org/10.1021/acs.inorgchem.9b03341	journal	April 2020
Diels-Alder in Aqueous Molecular Hosts: Unusual Regioselectivity and Efficient Catalysis Yoshizawa, M. Science, Vol. 312, Issue 5771 https://doi.org/10.1126/science.1124985	journal	April 2006
Stabilization of Labile Carbonyl Addition Intermediates by a Synthetic Receptor Iwasawa, T.; Hooley, R. J.; Rebek, J. Science, Vol. 317, Issue 5837 https://doi.org/10.1126/science.1143272	journal	July 2007
Multifunctional Charge and Hydrogen‐Bond Effects of Second‐Sphere Imidazolium Pendants Promote Capture and Electrochemical Reduction of CO ₂ in Water Catalyzed by Iron Porphyrins** Narouz, Mina R.; De La Torre, Patricia; An, Lun Angewandte Chemie International Edition, Vol. 61, Issue 37 https://doi.org/10.1002/anie.202207666	journal	August 2022
Ultraefficient homogeneous catalyst for the CO ₂ -to-CO electrochemical conversion Costentin, Cyrille; Passard, Guillaume; Robert, Marc Proceedings of the National Academy of Sciences, Vol. 111, Issue 42 https://doi.org/10.1073/pnas.1416697111	journal	October 2014
Porous Molecular Solids and Liquids Cooper, Andrew I. ACS Central Science, Vol. 3, Issue 6 https://doi.org/10.1021/acscentsci.7b00146	journal	May 2017
Post-synthetic modification of porous organic cages Wang, Hailong; Jin, Yinghua; Sun, Nana Chemical Society Reviews, Vol. 50, Issue 16 https://doi.org/10.1039/D0CS01142H	journal	January 2021
2D Covalent Organic Frameworks as Intrinsic Photocatalysts for Visible Light-Driven CO 2 Reduction Yang, Sizhuo; Hu, Wenhui; Zhang, Xin Journal of the American Chemical Society, Vol. 140, Issue 44 https://doi.org/10.1021/jacs.8b09705	journal	October 2018
A guide to secondary coordination sphere editing Drover, Marcus W. Chemical Society Reviews, Vol. 51, Issue 6 https://doi.org/10.1039/D2CS00022A	journal	January 2022
Supramolecular Tuning Enables Selective Oxygen Reduction Catalyzed by Cobalt Porphyrins for Direct Electrosynthesis of Hydrogen Peroxide Smith, Peter T.; Kim, Younghoon; Benke, Bahiru Punja Angewandte Chemie International Edition, Vol. 59, Issue 12 https://doi.org/10.1002/anie.201916131	journal	January 2020
Dissection of Light‐Induced Charge Accumulation at a Highly Active Iron Porphyrin: Insights in the Photocatalytic CO₂ Reduction Pugliese, Eva; Gotico, Philipp; Wehrung, Iris Angewandte Chemie, Vol. 134, Issue 14 https://doi.org/10.1002/ange.202117530	journal	February 2022
Supramolecular Catalysis in Metal–Ligand Cluster Hosts Brown, Casey J.; Toste, F. Dean; Bergman, Robert G. Chemical Reviews, Vol. 115, Issue 9 https://doi.org/10.1021/cr4001226	journal	April 2015
Oriented Electrostatic Effects on O₂ and CO₂ Reduction by a Polycationic Iron Porphyrin Martin, Daniel J.; Mayer, James M. Journal of the American Chemical Society, Vol. 143, Issue 30 https://doi.org/10.1021/jacs.1c03132	journal	July 2021
Covalent Organic Framework Based Functional Materials: Important Catalysts for Efficient CO₂Utilization Lu, Meng; Zhang, Mi; Liu, Jiang Angewandte Chemie, Vol. 134, Issue 15 https://doi.org/10.1002/ange.202200003	journal	February 2022
Catalysis of the electrochemical reduction of carbon dioxide Costentin, Cyrille; Robert, Marc; Savéant, Jean-Michel Chem. Soc. Rev., Vol. 42, Issue 6 https://doi.org/10.1039/C2CS35360A	journal	January 2013
Bioinspiration in light harvesting and catalysis Proppe, Andrew H.; Li, Yuguang C.; Aspuru-Guzik, Alán Nature Reviews Materials, Vol. 5, Issue 11 https://doi.org/10.1038/s41578-020-0222-0	journal	August 2020
Synthesis and Applications of Porous Organic Cages Evans, Jack D.; Sumby, Christopher J.; Doonan, Christian J. Chemistry Letters, Vol. 44, Issue 5 https://doi.org/10.1246/cl.150021	journal	May 2015
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V. Angewandte Chemie International Edition, Vol. 41, Issue 14, p. 2596-2599 https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4	journal	July 2002
Second-Sphere Biomimetic Multipoint Hydrogen-Bonding Patterns to Boost CO ₂ Reduction of Iron Porphyrins Gotico, Philipp; Boitrel, Bernard; Guillot, Régis Angewandte Chemie International Edition, Vol. 58, Issue 14 https://doi.org/10.1002/anie.201814339	journal	February 2019
Efficient electron transmission in covalent organic framework nanosheets for highly active electrocatalytic carbon dioxide reduction Zhu, Hong-Jing; Lu, Meng; Wang, Yi-Rong Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-019-14237-4	journal	January 2020
Metallosupramolecular cages: from design principles and characterisation techniques to applications McConnell, Anna J. Chemical Society Reviews, Vol. 51, Issue 8 https://doi.org/10.1039/D1CS01143J	journal	January 2022
Enzyme Mimics: Advances and Applications Kuah, Evelyn; Toh, Seraphina; Yee, Jessica Chemistry - A European Journal, Vol. 22, Issue 25 https://doi.org/10.1002/chem.201504394	journal	April 2016
Dissection of Electronic Substituent Effects in Multielectron–Multistep Molecular Catalysis. Electrochemical CO ₂ -to-CO Conversion Catalyzed by Iron Porphyrins Azcarate, Iban; Costentin, Cyrille; Robert, Marc The Journal of Physical Chemistry C, Vol. 120, Issue 51 https://doi.org/10.1021/acs.jpcc.6b09947	journal	December 2016
Earth-Abundant Photocatalytic CO ₂ Reduction by Multielectron Chargeable Cobalt Porphyrin Catalysts: High CO/H ₂ Selectivity in Water Based on Phase Mismatch in Frontier MO Association Zhang, Xian; Yamauchi, Kosei; Sakai, Ken ACS Catalysis, Vol. 11, Issue 16 https://doi.org/10.1021/acscatal.1c02475	journal	August 2021
Post-synthetic modifications of metal–organic cages Liu, Jinjin; Wang, Zhifang; Cheng, Peng Nature Reviews Chemistry, Vol. 6, Issue 5 https://doi.org/10.1038/s41570-022-00380-y	journal	April 2022
Quick and Easy Method to Dramatically Improve the Electrochemical CO ₂ Reduction Activity of an Iron Porphyrin Complex Kosugi, Kento; Kondo, Mio; Masaoka, Shigeyuki Angewandte Chemie, Vol. 133, Issue 40 https://doi.org/10.1002/ange.202110190	journal	August 2021
Atropisomeric Hydrogen Bonding Control for CO ₂ Binding and Enhancement of Electrocatalytic Reduction at Iron Porphyrins Gotico, Philipp; Roupnel, Loïc; Guillot, Regis Angewandte Chemie, Vol. 132, Issue 50 https://doi.org/10.1002/ange.202010859	journal	October 2020
A Supramolecular Strategy for Selective Catalytic Hydrogenation Independent of Remote Chain Length Bender, Trandon A.; Bergman, Robert G.; Raymond, Kenneth N. Journal of the American Chemical Society, Vol. 141, Issue 30 https://doi.org/10.1021/jacs.9b05604	journal	July 2019
Secondary-Sphere Effects in Molecular Electrocatalytic CO2 Reduction Nichols, Asa W.; Machan, Charles W. Frontiers in Chemistry, Vol. 7 https://doi.org/10.3389/fchem.2019.00397	journal	June 2019
Reticular Electronic Tuning of Porphyrin Active Sites in Covalent Organic Frameworks for Electrocatalytic Carbon Dioxide Reduction Diercks, Christian S.; Lin, Song; Kornienko, Nikolay Journal of the American Chemical Society, Vol. 140, Issue 3 https://doi.org/10.1021/jacs.7b11940	journal	January 2018
Consistent inclusion of continuum solvation in energy decomposition analysis: theory and application to molecular CO ₂ reduction catalysts Mao, Yuezhi; Loipersberger, Matthias; Kron, Kareesa J. Chemical Science, Vol. 12, Issue 4 https://doi.org/10.1039/D0SC05327A	journal	January 2021
Atomar dispergierte Metallzentren in Metall-organischen Gerüststrukturen für die elektrokatalytische und photokatalytische Energieumwandlung Liang, Zibin; Qu, Chong; Xia, Dingguo Angewandte Chemie, Vol. 130, Issue 31 https://doi.org/10.1002/ange.201800269	journal	June 2018
Multifunctional Charge and Hydrogen‐Bond Effects of Second‐Sphere Imidazolium Pendants Promote Capture and Electrochemical Reduction of CO₂in Water Catalyzed by Iron Porphyrins** Narouz, Mina R.; De La Torre, Patricia; An, Lun Angewandte Chemie, Vol. 134, Issue 37 https://doi.org/10.1002/ange.202207666	journal	August 2022
Electrocatalytic reduction of low concentration CO ₂ Kumagai, Hiromu; Nishikawa, Tetsuya; Koizumi, Hiroki Chemical Science, Vol. 10, Issue 6 https://doi.org/10.1039/C8SC04124E	journal	January 2019
Enhanced Hydrogenation of Carbon Dioxide to Methanol by a Ruthenium Complex with a Charged Outer-Coordination Sphere Erickson, Jeremy D.; Preston, Andrew Z.; Linehan, John C. ACS Catalysis, Vol. 10, Issue 13 https://doi.org/10.1021/acscatal.0c02268	journal	June 2020
Towards molecular understanding of local chemical environment effects in electro- and photocatalytic CO2 reduction Wagner, Andreas; Sahm, Constantin D.; Reisner, Erwin Nature Catalysis, Vol. 3, Issue 10 https://doi.org/10.1038/s41929-020-00512-x	journal	September 2020
Quantitative Electro-Reduction of CO₂ to Liquid Fuel over Electro-Synthesized Metal–Organic Frameworks Kang, Xinchen; Wang, Bin; Hu, Kui Journal of the American Chemical Society, Vol. 142, Issue 41 https://doi.org/10.1021/jacs.0c05913	journal	September 2020
Activating a Low Overpotential CO ₂ Reduction Mechanism by a Strategic Ligand Modification on a Ruthenium Polypyridyl Catalyst Johnson, Ben A.; Maji, Somnath; Agarwala, Hemlata Angewandte Chemie, Vol. 128, Issue 5 https://doi.org/10.1002/ange.201508490	journal	December 2015
Metal-Organic Frameworks for CO ₂ Chemical Transformations He, Hongming; Perman, Jason A.; Zhu, Guangshan Small, Vol. 12, Issue 46 https://doi.org/10.1002/smll.201602711	journal	October 2016
Selective and Efficient Photocatalytic CO ₂ Reduction to CO Using Visible Light and an Iron-Based Homogeneous Catalyst Bonin, Julien; Robert, Marc; Routier, Mathilde Journal of the American Chemical Society, Vol. 136, Issue 48 https://doi.org/10.1021/ja510290t	journal	November 2014
An NADH-Inspired Redox Mediator Strategy to Promote Second-Sphere Electron and Proton Transfer for Cooperative Electrochemical CO ₂ Reduction Catalyzed by Iron Porphyrin Smith, Peter T.; Weng, Sophia; Chang, Christopher J. Inorganic Chemistry, Vol. 59, Issue 13 https://doi.org/10.1021/acs.inorgchem.0c01162	journal	June 2020
Iodide-Selective Synthetic Ion Channels Based on Shape-Persistent Organic Cages Benke, Bahiru Punja; Aich, Pulakesh; Kim, Younghoon Journal of the American Chemical Society, Vol. 139, Issue 22 https://doi.org/10.1021/jacs.7b02708	journal	May 2017
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
CO ₂ Reduction: From Homogeneous to Heterogeneous Electrocatalysis Zhang, Sheng; Fan, Qun; Xia, Rong Accounts of Chemical Research, Vol. 53, Issue 1 https://doi.org/10.1021/acs.accounts.9b00496	journal	December 2019
Iron Porphyrins Embedded into a Supramolecular Porous Organic Cage for Electrochemical CO 2 Reduction in Water Smith, Peter T.; Benke, Bahiru Punja; Cao, Zhi Angewandte Chemie International Edition, Vol. 57, Issue 31 https://doi.org/10.1002/anie.201803873	journal	July 2018
Synergistic electroreduction of carbon dioxide to carbon monoxide on bimetallic layered conjugated metal-organic frameworks Zhong, Haixia; Ghorbani-Asl, Mahdi; Ly, Khoa Hoang Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-15141-y	journal	March 2020
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
Metal–Ligand Cooperativity via Exchange Coupling Promotes Iron- Catalyzed Electrochemical CO ₂ Reduction at Low Overpotentials Derrick, Jeffrey S.; Loipersberger, Matthias; Chatterjee, Ruchira Journal of the American Chemical Society, Vol. 142, Issue 48 https://doi.org/10.1021/jacs.0c10664	journal	November 2020
Templating Bicarbonate in the Second Coordination Sphere Enhances Electrochemical CO ₂ Reduction Catalyzed by Iron Porphyrins Derrick, Jeffrey S.; Loipersberger, Matthias; Nistanaki, Sepand K. Journal of the American Chemical Society, Vol. 144, Issue 26 https://doi.org/10.1021/jacs.2c02972	journal	June 2022
Maximizing Electroactive Sites in a Three‐Dimensional Covalent Organic Framework for Significantly Improved Carbon Dioxide Reduction Electrocatalysis Han, Bin; Jin, Yucheng; Chen, Baotong Angewandte Chemie, Vol. 134, Issue 1 https://doi.org/10.1002/ange.202114244	journal	November 2021
Urea-Based Multipoint Hydrogen-Bond Donor Additive Promotes Electrochemical CO ₂ Reduction Catalyzed by Nickel Cyclam Nichols, Eva M.; Chang, Christopher J. Organometallics, Vol. 38, Issue 6 https://doi.org/10.1021/acs.organomet.8b00308	journal	July 2018
Positional effects of second-sphere amide pendants on electrochemical CO ₂ reduction catalyzed by iron porphyrins Nichols, Eva M.; Derrick, Jeffrey S.; Nistanaki, Sepand K. Chemical Science, Vol. 9, Issue 11 https://doi.org/10.1039/C7SC04682K	journal	January 2018
Electrocatalytic and homogeneous approaches to conversion of CO ₂ to liquid fuels Benson, Eric E.; Kubiak, Clifford P.; Sathrum, Aaron J. Chem. Soc. Rev., Vol. 38, Issue 1 https://doi.org/10.1039/B804323J	journal	January 2009
Synergistic Effects of Imidazolium-Functionalization on fac -Mn(CO) ₃ Bipyridine Catalyst Platforms for Electrocatalytic Carbon Dioxide Reduction Sung, Siyoung; Li, Xiaohui; Wolf, Lucienna M. Journal of the American Chemical Society, Vol. 141, Issue 16 https://doi.org/10.1021/jacs.8b13657	journal	March 2019
Metal–Organic Framework‐Based Electrocatalysts for CO ₂ Reduction Shah, Syed Shoaib Ahmad; Najam, Tayyaba; Wen, Ming Small Structures, Vol. 3, Issue 5 https://doi.org/10.1002/sstr.202100090	journal	September 2021
Maximizing Electroactive Sites in a Three‐Dimensional Covalent Organic Framework for Significantly Improved Carbon Dioxide Reduction Electrocatalysis Han, Bin; Jin, Yucheng; Chen, Baotong Angewandte Chemie International Edition, Vol. 61, Issue 1 https://doi.org/10.1002/anie.202114244	journal	November 2021
Porphyrin Boxes: Rationally Designed Porous Organic Cages Hong, Soonsang; Rohman, Md. Rumum; Jia, Jiangtao Angewandte Chemie, Vol. 127, Issue 45 https://doi.org/10.1002/ange.201505531	journal	August 2015
Frontiers, Opportunities, and Challenges in Biochemical and Chemical Catalysis of CO ₂ Fixation Appel, Aaron M.; Bercaw, John E.; Bocarsly, Andrew B. Chemical Reviews, Vol. 113, Issue 8 https://doi.org/10.1021/cr300463y	journal	June 2013
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V. Angewandte Chemie, Vol. 114, Issue 14, p. 2708-2711 https://doi.org/10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0	journal	July 2002

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Carbon Dioxide Reduction
Electrocatalysis
Photocatalysis
Porous Cage
Second-Sphere

Title: Synergistic Porosity and Charge Effects in a Supramolecular Porphyrin Cage Promote Efficient Photocatalytic CO2 Reduction**

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