Structurally Asymmetric Nonplanar π‐Conjugated Naphthoquinone Derivatives Modified from Natural Lawsone for High‐Stability Aqueous Redox Flow Batteries
Abstract
Abstract Aqueous organic redox flow batteries (AORFBs) have attracted growing interest for grid‐scale energy storage by reducing reliance on scarce mineral resources used in transition metal‐based systems. Natural naphthoquinone derivatives, while environmentally friendly and abundant, suffer from poor solubility and electrochemical instability, hindering their practical use in AORFBs. To address these challenges, we report the functionalization of a naturally abundant dye, lawsone (i.e., 2‐HNQ), through non‐planar π‐conjugation extension and asymmetric intramolecular charge distribution, yielding a non‐planar π‐conjugated polar naphthoquinone derivative (namely BANQ) with enhanced water solubility and redox reversibility. Computational simulations and spectroscopic analysis confirmed that the introduction of benzoic acid group imparts a polar π‐conjugation extended structure with asymmetric charge distribution. This structural modification efficiently enhances aqueous solubility and suppresses degradation pathways, such as Michael addition and irreversible keto‐enol tautomerism. Compared with 2‐HNQ precursor, BANQ exhibits lower sensitivity to nucleophilic and electrophilic attacks. The BANQ anolyte exhibited a very low‐capacity decay rate of merely 0.00018% per cycle (or 0.045% per day), representing a two‐order‐of‐magnitude reduction compared to that of 2‐HNQ (0.032% per cycle or 8.22% per day). This study highlights the potential of modifying natural‐derived products with rationally designed conjugated electron structure for green and sustainable energy storage solutions.
Article Details
Authors (15)
Pengbo Zhang
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Green Energy Catalysis and Intelligent Chemical Engineering, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technologies Research Center, Institute of Green Chemistry and Engineering, School of Chemistry and Chemical Engineering
Sheng Wen
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Green Energy Catalysis and Intelligent Chemical Engineering, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technologies Research Center, Institute of Green Chemistry and Engineering, School of Chemistry and Chemical Engineering
Yongkang Chen
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Advanced Organic Materials, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technology Research Center, Institute of Green Chemistry and Engineering, School of Sustainable Energy and Resources, School of Chemistry and Chemical Engineering
Yuzhu Liu
Jie Wei
College of Energy, College of Materials, State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, School of Life Sciences, College of Physical Science and Technology, Discipline of Intelligent Instrument and Equipment, iChEM, Fujian Key Laboratory of Advanced Materials
Zuoao Wu
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Advanced Organic Materials, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technology Research Center, Institute of Green Chemistry and Engineering, School of Sustainable Energy and Resources, School of Chemistry and Chemical Engineering
Guochun Ding
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Advanced Organic Materials, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technology Research Center, Institute of Green Chemistry and Engineering, School of Sustainable Energy and Resources, School of Chemistry and Chemical Engineering
Xinmei Song
Key Laboratory of Luminescence Analysis and Molecular Sensing, Ministry of Education, School of Chemistry and Chemical Engineering
Tengfei Dai
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Advanced Organic Materials, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technology Research Center, Institute of Green Chemistry and Engineering, School of Sustainable Energy and Resources, School of Chemistry and Chemical Engineering
Zhihu You
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Green Energy Catalysis and Intelligent Chemical Engineering, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technologies Research Center, Institute of Green Chemistry and Engineering, School of Chemistry and Chemical Engineering
Qingbo Guo
State Key Laboratory of Coordination Chemistry MOE Key Laboratory of Mesoscopic Chemistry MOE Key Laboratory of High Performance Polymer Materials and Technology Jiangsu Key Laboratory of Green Energy Catalysis and Intelligent Chemical Engineering Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices Tianchang New Materials and Energy Technologies Research Center Institute of Green Chemistry and Engineering School of Chemistry and Chemical Engineering Nanjing...
Peng Liu
Jianwen Guo
Zuoxiu Tie
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Green Energy Catalysis and Intelligent Chemical Engineering, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technologies Research Center, Institute of Green Chemistry and Engineering, School of Chemistry and Chemical Engineering
Zhong Jin
State Key Laboratory of Coordination Chemistry, MOE Key Laboratory of Mesoscopic Chemistry, MOE Key Laboratory of High Performance Polymer Materials and Technology, Jiangsu Key Laboratory of Green Energy Catalysis and Intelligent Chemical Engineering, Suzhou Key Laboratory of Green Intelligent Manufacturing of New Energy Materials and Devices, Tianchang New Materials and Energy Technologies Research Center, Institute of Green Chemistry and Engineering, School of Chemistry and Chemical Engineering