Bridged-Ring Nitroxy Organic Materials for Flow Battery Energy Density

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Solution Overview

Problem

Organic active materials for electrochemical cells face challenges in achieving high stability and energy density due to their large molecular size and low redox potential, particularly in flow batteries which suffer from low energy density and frequent refueling needs.

Innovation Solution

The use of bridged-ring organic molecules with a nitroxy moiety, capable of existing in three redox states, combined with fluoroalkylsulfonyl salts to form solvate-ionic liquids, enabling high coulombic efficiency and energy density, and allowing the organic active material to be used as a fluid in flow batteries.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If organic active materials are used in flow batteries, then the battery can be quickly recharged by refueling, but the energy density is low requiring frequent refueling

Engineering Contradiction:
Improverecharging speedVSAvoidenergy density
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent changes the chemical parameters of the organic active material by introducing a nitroxy moiety capable of three redox states (aminoxy anion, nitroxide radical, oxoammonium cation). This enables a two-electron transfer process, effectively doubling the charge transfer capability per molecule and thus the energy density, while maintaining the liquid state necessary for rapid refueling in flow batteries

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining a bridged-ring organic framework with a nitroxy functional group. This composite structure integrates the stability of the bridged-ring system with the redox activity of the nitroxy moiety, achieving both high stability over multiple cycles and high energy density through two-electron transfer capability

Inventive Principle:
Principle #40Composite materials

2Adaptability or versatility

If organic active materials are designed with large molecular size, then chemical modification capability is improved, but energy density decreases

Engineering Contradiction:
Improvechemical modification capabilityVSAvoidenergy density
Core Design Contradiction:
Adaptability or versatilityVSQuantity of substance

Solution Approach 1:

The patent optimizes the molecular parameters by using a compact bridged-ring structure that minimizes molecular volume while incorporating a nitroxy group capable of two-electron transfer. This parameter optimization achieves high energy density despite the relatively large molecular size required for chemical versatility

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by concentrating the redox activity in the nitroxy moiety while keeping the bridged-ring framework relatively compact. The nitroxy group serves as the functional center for electron transfer, allowing the rest of the molecule to be optimized for stability and fluidity without excessive size

Inventive Principle:
Principle #3Local quality

3Weight of moving object

If organic active materials are used, then lightweight and chemical modification are achieved, but stability over multiple charge/discharge cycles is poor

Engineering Contradiction:
ImproveweightVSAvoidstability over charge/discharge cycles
Core Design Contradiction:
Weight of moving objectVSReliability

Solution Approach 1:

The patent creates a composite structure where the bridged-ring framework provides structural stability and resistance to degradation over multiple cycles, while the nitroxy moiety provides the necessary redox activity. This composite design maintains both lightweight properties and cycle stability

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The bridged-ring structure serves as a protective framework that stabilizes the nitroxy group during repeated oxidation and reduction cycles. This pre-designed stable framework cushions the nitroxy moiety from degradation, enabling long-term cycling stability

Inventive Principle:
Principle #11Beforehand cushioning (Prior cushioning)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This configuration supports high coulombic efficiency and energy density, enabling rapid recharging and extended operation in flow batteries with improved stability and energy storage capacity.

Implementation Method 1

The organic active material is configured to undergo reversible electrochemical reduction/oxidation between any redox state including aminoxy anion, nitroxide radical, and oxoammonium cation

Methodology Applied
Scientific EffectRedox reactions: Redox Reactions

Implementation Method 2

The electrolyte composition comprises a solvate-ionic liquid that includes a fluoroalkylsulfonyl salt and a bridged-ring, organic molecule having a nitroxy moiety

Methodology Applied
Scientific EffectSolvation: Solvation

Data Source

PatentUS9911978B2Organic active materials for rechargeable battery
Publication Date: 2018.03.06 KK TOYOTA CHUO KENKYUSHO
  • US9911978B2 patent drawing
  • US9911978B2 patent drawing
  • US9911978B2 patent drawing

AI summary

An organic active material, having good energy density and electrochemical stability, for use in an electrochemical cell is disclosed. Electrochemical cells that employ the organic active material are also disclosed. The organic active material is a bridged-ring organic molecule having a nitroxy moiety, the nitroxy moiety being capable of two-electron oxidation/reduction through three distinct redox states. In different implementations, the organic active material can be incorporated in a solid electrode or can be employed as a fluid active material such as is useful for a flow cell. In different variations, the organic active material can be employed as a cathodic active material or as an anodic active material.