Proton‐Resistant <i>N</i> ‐Heterocycle‐Linked TEMPO Catholytes for Long‐Lasting Neutral Aqueous Organic Redox Flow Batteries

Y Yujie Zhao (Department of Chemistry) X Xu Liu Z Zengrong Wang (Frontier 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) J Jiapeng Huang J Junjie Huang X Xiaotong Deng (Frontier Institute of Science and Technology Interdisciplinary Research Center of Frontier science and technology State Key Laboratory for Strength and Vibration of Mechanical Structures Institute of New Concept Sensors and Molecular Materials Shaanxi Key Laboratory of New Conceptual Sensors and Molecular Materials Engineering Research Center of Key Materials for Efficient Utilization of Clean Energy of Shaanxi Province National innovation Platform (Center) for Industry‐Education Integration of...) X Xuri Zhang (Frontier 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) H Heng Zhang H Haiyan Yu (State Key Laboratory of Tropical Oceanography, South China Sea Institute of Oceanology, Guangdong Provincial Key Laboratory of Applied Marine Biology, Chinese Academy of Sciences) Y Ya‐Ke Li (MOE Key Laboratory for Non‐Equilibrium Synthesis and Modulation of Condensed Matter School of Physics Xi'an Jiao tong University Xi'an Shaanxi Province 710049 P.R. China) G Gao‐Lei Hou (MOE Key Laboratory for Non‐Equilibrium Synthesis and Modulation of Condensed Matter School of Physics Xi'an Jiao tong University Xi'an Shaanxi Province 710049 P.R. China) G Gang He

Abstract

Abstract TEMPO is a widely studied catholyte for aqueous organic redox flow batteries (AORFBs) but suffers from proton‐induced ring‐opening degradation when its solubility is enhanced via hydrophilic substitution at the 4‐position, leading to structural failure and rapid capacity fade. To address this issue, five TEMPO derivatives were synthesized through N ‐acetylamino bridging and nitrogen‐containing heterocycle grafting strategy. Combined analyses using atomic dipole moment‐corrected Hirshfeld (ADCH) charges, Fukui functions, and linear ion trap mass spectrometry (LTQ‐XL) reveal that aromatic heterocycle functionalization enables favorable charge redistribution during redox cycling, enhancing both redox kinetics and molecular stability. In particular, dimethylaminopyridine‐functionalized TEMPO (DMA‐TEMPO) exhibits enhanced π‐conjugation and basicity, which suppresses proton‐driven ring‐opening and significantly improves structural resilience. 1 M DMA‐TEMPO catholyte delivers exceptional cycling performance, retaining 99.98% of its capacity after 560 cycles, while 2 M system maintains 97% capacity over 100 cycles. Compared to its structural analog 1 M PA‐TEMPO, the cycle life is improved 18‐fold. This study offers a robust molecular design strategy for developing proton‐resistant catholytes, advancing the practical deployment of long‐lasting AORFBs for grid‐scale energy storage.

Article Details

Volume / Issue Vol. 64, Issue 47
Published November 17, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (12)

Y

Yujie Zhao

Department of Chemistry

X

Xu Liu

Z

Zengrong Wang

Frontier 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

J

Jiapeng Huang

J

Junjie Huang

X

Xiaotong Deng

Frontier Institute of Science and Technology Interdisciplinary Research Center of Frontier science and technology State Key Laboratory for Strength and Vibration of Mechanical Structures Institute of New Concept Sensors and Molecular Materials Shaanxi Key Laboratory of New Conceptual Sensors and Molecular Materials Engineering Research Center of Key Materials for Efficient Utilization of Clean Energy of Shaanxi Province National innovation Platform (Center) for Industry‐Education Integration of...

X

Xuri Zhang

Frontier 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

H

Heng Zhang

H

Haiyan Yu

State Key Laboratory of Tropical Oceanography, South China Sea Institute of Oceanology, Guangdong Provincial Key Laboratory of Applied Marine Biology, Chinese Academy of Sciences

Y

Ya‐Ke Li

MOE Key Laboratory for Non‐Equilibrium Synthesis and Modulation of Condensed Matter School of Physics Xi'an Jiao tong University Xi'an Shaanxi Province 710049 P.R. China

G

Gao‐Lei Hou

MOE Key Laboratory for Non‐Equilibrium Synthesis and Modulation of Condensed Matter School of Physics Xi'an Jiao tong University Xi'an Shaanxi Province 710049 P.R. China

G

Gang He