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    Effect of Molecular Structure of Quinones and Carbon Electrode Surfaces on the Interfacial Electron Transfer Process
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    • Graziela C. Sedenho
      Graziela C. Sedenho
      São Carlos Institute of Chemistry, University of São Paulo (USP), São Carlos, São Paulo 13560-970, Brazil
      Harvard John A. Paulson School of Engineering and Applied Sciences, Cambridge, Massachusetts 02138, United States
      More by Graziela C. Sedenho
      Orcidhttp://orcid.org/0000-0001-8696-5978
    • Diana De Porcellinis
      Diana De Porcellinis
      Harvard John A. Paulson School of Engineering and Applied Sciences, Cambridge, Massachusetts 02138, United States
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    • Yan Jing
      Yan Jing
      Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States
      More by Yan Jing
      Orcidhttp://orcid.org/0000-0002-5669-4609
    • Emily Kerr
      Emily Kerr
      Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States
      More by Emily Kerr
    • Luis Martin Mejia-Mendoza
      Luis Martin Mejia-Mendoza
      Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States
      More by Luis Martin Mejia-Mendoza
    • Álvaro Vazquez-Mayagoitia
      Álvaro Vazquez-Mayagoitia
      Argonne Leadership Computing Facility, Argonne National Laboratory, Argonne, Illinois 60439, United States
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    • Alán Aspuru-Guzik
      Alán Aspuru-Guzik
      Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States
      Department of Chemistry and Department of Computer Science, University of Toronto, Toronto, Ontario M5S 3H6, Canada
      More by Alán Aspuru-Guzik
      Orcidhttp://orcid.org/0000-0002-8277-4434
    • Roy G. Gordon
      Roy G. Gordon
      Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States
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      Orcidhttp://orcid.org/0000-0001-5980-268X
    • Frank N. Crespilho*
      Frank N. Crespilho
      São Carlos Institute of Chemistry, University of São Paulo (USP), São Carlos, São Paulo 13560-970, Brazil
      Harvard John A. Paulson School of Engineering and Applied Sciences, Cambridge, Massachusetts 02138, United States
      *E-mail [email protected]
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      Orcidhttp://orcid.org/0000-0003-4830-652X
    • Michael J. Aziz*
      Michael J. Aziz
      Harvard John A. Paulson School of Engineering and Applied Sciences, Cambridge, Massachusetts 02138, United States
      *E-mail [email protected]
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      Orcidhttp://orcid.org/0000-0001-9657-9456
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    ACS Applied Energy Materials

    Cite this: ACS Appl. Energy Mater. 2020, 3, 2, 1933–1943
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    https://doi.org/10.1021/acsaem.9b02357
    Published January 28, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    Quinones can undergo thermodynamically reversible proton-coupled electron transfer reactions and are being applied as electroactive compounds in aqueous organic batteries. However, the electrochemical reversibility of these compounds is affected not only by their molecular structure but also by the properties of a carbon-based electrode surface. This study combines experimental and theoretical approaches to understand this dependence. We study the electron transfer kinetics of two synthesized quinone derivatives and two commercially available ones with a glassy carbon, a highly ordered pyrolytic graphite, and a high-edge-density graphite electrode (HEDGE). The electrochemical reversibility is notably improved on the HEDGE, which shows a higher density of defects and presents oxygenated functional groups at its surface. The electron transfer kinetics are controlled by adsorbed species onto the HEDGE. Molecular dynamics simulation and quantum mechanics calculations suggest defects with oxygen-containing functional groups, such as C–O and C═O, on HEDGE surfaces drive the interaction with the functional groups of the molecules, during physisorption from van der Waals forces. The presence of sulfonic acid side groups and a greater number of aromatic rings in the molecular structure may contribute to a higher stabilization of quinone derivatives on HEDGEs. We propose that high-performance carbon-based electrodes can be obtained without catalysts for organic batteries, by the engineering of carbon-based surfaces with edge-like defects and oxygenated functional groups.

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    • Synthesis and characterization of the FQ and CQ; detailed experimental procedures and computational calculations (PDF)

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    ACS Applied Energy Materials

    Cite this: ACS Appl. Energy Mater. 2020, 3, 2, 1933–1943
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsaem.9b02357
    Published January 28, 2020
    Copyright © 2020 American Chemical Society
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