Quinone-Containing Poly(arylene) Synthesis for Gas Separation

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Solution Overview

Problem

Current methods for electroswing adsorption, such as those using Ni(0)-catalyzed Yamamoto polymerization for quinone-containing poly(arylene)s, are costly and lack efficient synthetic alternatives, limiting their application in electrochemical gas separations and energy storage.

Innovation Solution

Development of quinone-containing poly(arylene)s using dihalogenated naphthoquinones and benzoquinones with palladium catalysts, enabling efficient Suzuki polycondensation for improved conductivity and reactivity, suitable for electrochemical applications like gas separation and energy storage.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If Ni(0)-catalyzed Yamamoto polymerization is used to synthesize quinone-containing poly(arylene)s, then the polymer can be produced, but the synthesis cost is high and productivity is low

Engineering Contradiction:
Improvesynthesis costVSAvoidsynthesis efficiency
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent changes the catalytic system from Ni(0) to Pd-catalyzed Suzuki polycondensation, altering the reaction parameters to achieve both cost-effectiveness and high productivity. The Pd catalyst enables milder reaction conditions and faster polymerization kinetics while maintaining polymer quality

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the Yamamoto polymerization mechanism with Suzuki polycondensation mechanism, substituting one chemical synthesis pathway with another that offers superior economic and efficiency characteristics while achieving the same polymerization objective

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

2Reliability

If conventional electroactive materials are used in electroswing adsorption, then gas capture function is achieved, but conductivity and reactivity are insufficient

Engineering Contradiction:
Improvegas capture functionVSAvoidconductivity and reactivity
Core Design Contradiction:
ReliabilityVSPower

Solution Approach 1:

The patent creates composite electrode structures by disposing quinone-containing poly(arylene) on conductive substrates such as carbon paper or carbon cloth. This composite approach combines the gas capture capability of quinone moieties with the electrical conductivity of carbon substrates, achieving both required functions simultaneously

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies different functional properties to different parts of the electrode system: the quinone-containing polymer provides localized gas capture function at the electrode surface, while the carbon substrate provides distributed electrical conductivity throughout the electrode structure

Inventive Principle:
Principle #3Local quality

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

The new approach provides a cost-effective and efficient synthesis of quinone-containing poly(arylene)s with favorable reduction potentials, enhancing their application in electrochemical gas separations and energy storage by improving conductivity and processability.

Implementation Method 1

combining a dihalogenated naphthoquinone, a dihalogenated benzoquinone, or a combination thereof; and a substituted or unsubstituted C6-20 aryl diboronic acid or diboronic ester; in the presence of a palladium catalyst under conditions effective to provide the quinone-containing poly(arylene)

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

quinone-containing poly(arylene)s with favorable reduction potentials, enhancing their application in electrochemical gas separations and energy storage

Methodology Applied
Scientific EffectRedox reactions: Redox Reactions

Data Source

PatentUS12162980B2Quinone-containing poly(arylene), methods for the manufacture thereof, and use for electrochemical gas separation
Publication Date: 2024.12.10 VERDOX INC
  • US12162980B2 patent drawing
  • US12162980B2 patent drawing
  • US12162980B2 patent drawing

AI summary

A quinone-containing poly(arylene) includes repeating units of formula (I), (II), (III), (IV), (V), or (VI) as defined herein. The quinone-containing poly(arylene) can be useful in composites, electrode assemblies, electrochemical cells, gas separation systems, energy storage devices, and electrochromic devices.