Side-Chain Symmetry Breaking in Naphthalene Diimides Decouples High Concentration From Cycling Stability in Neutral Aqueous Organic Redox Flow Batteries.

Heng Zhang, Zhikang Han, Xu Liu, Xuri Zhang, Zengrong Wang, Haiyan Yu, Yawen Li, Gang He

Abstract read

In one paragraph

Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

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4 · The record

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5 · Who and what money

Authors and funding

8 authors.

Heng ZhangFrontier Institute of Science and Technology, Interdisciplinary Research Center of Frontier science and technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Engineering Research Center of Key Materials For Efficient Utilization of Clean Energy of Shaanxi Province, Xi'an Key Laboratory of Electronic Devices and Material Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China.

Zhikang HanFrontier Institute of Science and Technology, Interdisciplinary Research Center of Frontier science and technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Engineering Research Center of Key Materials For Efficient Utilization of Clean Energy of Shaanxi Province, Xi'an Key Laboratory of Electronic Devices and Material Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China.

Xu LiuFrontier Institute of Science and Technology, Interdisciplinary Research Center of Frontier science and technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Engineering Research Center of Key Materials For Efficient Utilization of Clean Energy of Shaanxi Province, Xi'an Key Laboratory of Electronic Devices and Material Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China.

Xuri ZhangFrontier Institute of Science and Technology, Interdisciplinary Research Center of Frontier science and technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Engineering Research Center of Key Materials For Efficient Utilization of Clean Energy of Shaanxi Province, Xi'an Key Laboratory of Electronic Devices and Material Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China.

Zengrong WangFrontier Institute of Science and Technology, Interdisciplinary Research Center of Frontier science and technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Engineering Research Center of Key Materials For Efficient Utilization of Clean Energy of Shaanxi Province, Xi'an Key Laboratory of Electronic Devices and Material Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China.

Haiyan YuFrontier Institute of Science and Technology, Interdisciplinary Research Center of Frontier science and technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Engineering Research Center of Key Materials For Efficient Utilization of Clean Energy of Shaanxi Province, Xi'an Key Laboratory of Electronic Devices and Material Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China.

Yawen LiFrontier Institute of Science and Technology, Interdisciplinary Research Center of Frontier science and technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Engineering Research Center of Key Materials For Efficient Utilization of Clean Energy of Shaanxi Province, Xi'an Key Laboratory of Electronic Devices and Material Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China.

Gang HeFrontier Institute of Science and Technology, Interdisciplinary Research Center of Frontier science and technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Engineering Research Center of Key Materials For Efficient Utilization of Clean Energy of Shaanxi Province, Xi'an Key Laboratory of Electronic Devices and Material Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China.ORCID https://orcid.org/0000-0002-5319-7084

Funding

China Postdoctoral Science Foundation 2025M780145Fundamental Research Funds for the Central Universities xzy012025108Fundamental Research Funds for the Central Universities xzy022025058Key Research and Development Program of Shaanxi Province-Critical Core Technology Project 2024CY-GJHX-02Key Research and Development Program of Shaanxi Province-Critical Core Technology Project 2025CY-JJQ-125National Natural Science Foundation of China 22175138National Natural Science Foundation of China 22201228National Natural Science Foundation of China 22205172National Natural Science Foundation of China 52303267Shaanxi Province Technological Innovation Guidance Special 2022QFY08-01

6 · The paper itself

Abstract

Neutral aqueous organic redox flow batteries (AORFBs) offer a promising pathway for transitioning renewables from supplementary to primary energy sources. However, their advancement is constrained by the limited long-term cycling stability and sluggish redox kinetics of materials under high-concentration conditions. Although introducing hydrophilic groups can mitigate these issues, highly symmetric molecular architectures often impose performance penalties. In this study, a series of asymmetrically modified naphthalene diimide derivatives were synthesized via a one-pot symmetry-breaking strategy, which diol-dex-NDI achieves a high solubility of 1.82 M. Density functional theory and Molecular dynamics simulations reveal that diol-dex-NDI preferentially adopts a dynamic antiparallel π-π stacking mode, enhancing thermodynamic stability while effectively suppressing molecular aggregation. In situ Raman spectroscopy uncovers hydration shell dynamics during electron transfer, showing a 35% reduction in desolvation energy barrier compared to dex-NDI. Furthermore, π-π and dipole interactions with the electrode enhance adsorption energy and accelerate electron transfer. This molecular design also strengthens the key C─N bond, as evidenced by increased bond dissociation energy, thereby intrinsically improving resistance to electrochemical degradation. Leveraging these advantages, 1.0 M (2 M e

Indexed as

alkaline resistancereactivity kineticsside‐chain symmetry‐breaking strategysolvation effectπ–π interaction

Identifiers

PMID42189700

DOI10.1002/anie.8798664

PMCPMC13427136

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.