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Pyrrolinium-Substituted Persistent Zwitterionic Ferrocenate Derivative Enabling the Application of Ferrocene Anolyte

Song, Hayoung and Kwon, Giyun and Citek, Cooper and Jeon, Seungwon and Kang, Kisuk and Lee, Eunsung (2021) Pyrrolinium-Substituted Persistent Zwitterionic Ferrocenate Derivative Enabling the Application of Ferrocene Anolyte. ACS Applied Materials and Interfaces . ISSN 1944-8244. doi:10.1021/acsami.1c11571. (In Press) https://resolver.caltech.edu/CaltechAUTHORS:20210713-214314626

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Abstract

Here, we report the imidazolium-/pyrrolinium-substituted persistent zwitterionic ferrocenate derivatives, which were characterized by electron paramagnetic resonance (EPR) and 57Fe Mössbauer spectroscopy. Additional theoretical studies on these zwitterionic ferrocenate derivatives clearly explain the origin of their thermal stability and the orbital interactions between iron and imidazolium-/pyrrolinium-substituted zwitterionic cyclopentadienyl ligand. Exploiting the facile Fe(II/I) redox chemistry, we successfully demonstrated that the pyrrolinium-substituted ferrocene derivative can be applied as an example of derivatized ferrocene anolyte for redox-flow batteries. These zwitterionic ferrocenate derivatives will not only deepen our understanding of the intrinsic chemistry of ferrocenate but have the potential to open the way for the rational design of metallocenate derivatives for various applications.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acsami.1c11571DOIArticle
https://doi.org/10.26434/chemrxiv.12687416.v3DOIDiscussion Paper - version 3
https://doi.org/10.26434/chemrxiv.12687416.v2DOIDiscussion Paper - version 2
https://doi.org/10.26434/chemrxiv.12687416.v1DOIDiscussion Paper - version 1
ORCID:
AuthorORCID
Song, Hayoung0000-0002-9225-3528
Citek, Cooper0000-0001-9376-8200
Kang, Kisuk0000-0002-8696-1886
Lee, Eunsung0000-0002-1507-098X
Alternate Title:The First Isolable Low-valent Ferrocene Enabling the Application of Unprecedented Ferrocene Anolyte, Low-Valent Ferrocenes
Additional Information:© 2021 American Chemical Society. Received: June 21, 2021; Accepted: September 15, 2021. The X-ray crystallography analysis with synchrotron radiation was performed at the Pohang Accelerator Laboratory (PLS-II BL2D SMC beamline). This work was supported by (1) the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (No. NRF-2016H1A2A1907122 – Global Ph.D. Fellowship Program, NRF-2019R1A2C2010732, and NRF-2019M1A2A2067940), (2) Creative Materials Discovery Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2017M3D1A1039553), (3) Institute for Basic Science (IBS-R006-A2), (4) Korea Electric Power Corporation (R20XO02-31), and (5) the postdoctoral research fellowship of POSTECH Initiative for fostering Unicorn of Research & Innovation (PIURI) project. We thank Prof. Jonas C. Peters for use of the Mössbauer spectroscopy and Dr. Ewa Pietrasiak for helpful discussions. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
National Research Foundation of KoreaNRF-2016H1A2A1907122
National Research Foundation of KoreaNRF-2019R1A2C2010732
National Research Foundation of KoreaNRF-2019M1A2A2067940
National Research Foundation of KoreaNRF-2017M3D1A1039553
Institute for Basic Science (Korea)IBS-R006-A2
Korea Electric Power CorporationR20XO02-31
Pohang University of Science and Technology (POSTECH)UNSPECIFIED
Subject Keywords:ferrocenate, zwitterion, N-heterocyclic carbene, redox-flow battery, anolyte
DOI:10.1021/acsami.1c11571
Record Number:CaltechAUTHORS:20210713-214314626
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210713-214314626
Official Citation:Pyrrolinium-Substituted Persistent Zwitterionic Ferrocenate Derivative Enabling the Application of Ferrocene Anolyte. Hayoung Song, Giyun Kwon, Cooper Citek, Seungwon Jeon, Kisuk Kang, and Eunsung Lee. ACS Applied Materials & Interfaces. Article ASAP; DOI: 10.1021/acsami.1c11571
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:109795
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Jul 2021 22:00
Last Modified:28 Sep 2021 17:45

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