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Stabilization of Naphthalene Diimide Anions by Ion Pair Formation in Nonaqueous Organic Redox Flow Batteries

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Title
Stabilization of Naphthalene Diimide Anions by Ion Pair Formation in Nonaqueous Organic Redox Flow Batteries
Author(s)
Ahn, Seongmo; Mina Son; Singh, Vikram; Yun, Ariyeong; Mu-Hyun Baik; Byon, Hye Ryung
Publication Date
2024-02
Journal
Journal of the American Chemical Society, v.146, no.7, pp.4521 - 4531
Publisher
American Chemical Society
Abstract
In redox flow batteries, a compelling strategy for enhancing the charge capacity of redox-active organic molecules involves storing multiple electrons within a single molecule. However, this approach poses unique challenges such as chemical instability by forming radicals, elevated energy requirements, and unsustainable charge concentration. Ion pairing is a possible solution to achieve charge neutrality and engineer redox potential shifts but has received limited attention. In this study, we demonstrate that Li+ can stabilize naphthalene diimide (NDI) anions dissolved in acetonitrile and significantly shift the second cathodic potential close to the first. Our findings, supported by density functional theory calculations and Fourier transform infrared spectroscopy, indicate that dimeric NDI species form stable ion pairs with Li+. Conversely, K+ ions exhibit weak interactions, and cyclic voltammograms confirm significant potential shifts when stronger Lewis acids and solvents with lower donor numbers are employed. Galvanostatic examinations reveal a single voltage plateau with Li+, which indicates a rapid redox process involving doubly charged NDI2- with Li+. These aggregated ion pairs offer the additional benefits of hindering crossover events, contributing to excellent cyclability, and suppressing undesirable side reactions even after 1000 redox cycles.
URI
https://pr.ibs.re.kr/handle/8788114/15017
DOI
10.1021/jacs.3c11176
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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