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Controlling π–π Interactions of Highly Soluble Naphthalene Diimide Derivatives for Neutral pH Aqueous Redox Flow Batteries

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Title
Controlling π–π Interactions of Highly Soluble Naphthalene Diimide Derivatives for Neutral pH Aqueous Redox Flow Batteries
Author(s)
Singh, Vikram; Seongyeon Kwon; Choi, Yunseop; Ahn, Seongmo; Gyumin Kang; Yi, Yelim; Lim, Mi Hee; Seo, Jongcheol; Mu-Hyun Baik; Byon, Hye Ryung
Publication Date
2023-03
Journal
ADVANCED MATERIALS, v.35, no.13
Publisher
WILEY-V C H VERLAG GMBH
Abstract
Organic redox-active molecules are a promising platform for designing sustainable, cheap, and safe charge carriers for redox flow batteries. However, radical formation during the electron-transfer process causes severe side reactions and reduces cyclability. This problem is mitigated by using naphthalene diimide (NDI) molecules and regulating their pi-pi interactions. The long-range pi-stacking of NDI molecules, which leads to precipitation, is disrupted by tethering four ammonium functionalities, and the solubility approaches 1.5 m in water. The gentle pi-pi interactions induce clustering and disassembling of the NDI molecules during the two-electron transfer processes. When the radical anion forms, the antiferromagnetic coupling develops tetramer and dimer and nullifies the radical character. In addition, short-range-order NDI clusters at 1 m concentration are not precipitated but inhibit crossover. They are disassembled in the subsequent electron-transfer process, and the negatively charged NDI core strongly interacts with ammonium groups. These behaviors afford excellent RFB performance, demonstrating 98% capacity retention for 500 cycles at 25 mA cm(-2) and 99.5% Coulombic efficiency with 2 m electron storage capacity.
URI
https://pr.ibs.re.kr/handle/8788114/13083
DOI
10.1002/adma.202210859
ISSN
0935-9648
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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