Sulfonated Polyphenylene Membranes With Controlled Ionic Group Placement

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

The challenge lies in synthesizing well-defined polymer backbones with sterically-encumbered, rigid aryl-aryl linkages for hydrocarbon-based proton exchange membranes, as existing methods face difficulties in achieving precise control over the placement of ionic functionalities and structural organization, leading to inefficient ionic conductivity and stability.

Innovation Solution

The development of a polymer with a repeating unit that allows for precise control of ionic group placement, utilizing a combination of aryl and heteroaryl substituents and linking heteroatoms to form a stable and organized polymer structure, enabling the synthesis of sulfonated phenylene oligomers and polymers with enhanced chemical and mechanical stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If post-sulfonation of polyphenylenes is used to introduce ionic functionality, then ionic conductivity is improved, but manufacturing precision and structural definition deteriorate due to random distribution of sulfonic acid groups

Engineering Contradiction:
Improveionic conductivityVSAvoidstructural definition
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent applies preliminary action by pre-installing directing groups (such as halogen atoms or other substituents) on the polyphenylene backbone at specific positions before introducing ionic functionality. These directing groups guide the subsequent sulfonation or other ionic group introduction reactions to occur at predetermined locations, ensuring precise spatial control over ionic group placement rather than random distribution. This preliminary structuring enables both high ionic conductivity through organized channels and well-defined polymer structure.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses intermediary directing groups as mediators between the polyphenylene backbone and the ionic functionality. These intermediary groups (such as halogen substituents, boronic acid groups, or other handle groups) serve as temporary placeholders that direct the introduction of ionic groups at specific positions. After the ionic groups are installed, the intermediary groups can be removed or transformed, leaving behind precisely positioned ionic functionality on the polymer backbone.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Strength

If rigid aryl-aryl linkages are used in polymer backbone, then mechanical strength is improved, but ease of manufacture deteriorates due to steric encumbrance and difficulty in forming linkages

Engineering Contradiction:
Improvemechanical strengthVSAvoidsynthesis difficulty
Core Design Contradiction:
StrengthVSEase of manufacture

Solution Approach 1:

The patent applies segmentation by dividing the polymer synthesis into distinct modular stages: first synthesizing well-defined oligomeric building blocks with controlled aryl-aryl linkages and specific functional groups, then assembling these pre-characterized modules into larger polymer structures. This segmentation allows each stage to be optimized independently, making the overall synthesis more manageable despite the presence of rigid aryl-aryl linkages. The modular approach enables precise control over backbone structure while maintaining ease of manufacture through standardized building block synthesis.

Inventive Principle:
Principle #1Segmentation

Data Source

PatentUS11802187B2Polyphenylenes, methods, and uses thereof
Publication Date: 2023.10.31 SIMON FRASER UNIVERSITY
  • US11802187B2 patent drawing
  • US11802187B2 patent drawing
  • US11802187B2 patent drawing

AI summary

Described herein are anionic phenylene oligomers and polymers, and devices including these materials. The oligomers and polymers can be prepared in a convenient and well-controlled manner, and can be used in cation exchange 5 membranes. Also described is the controlled synthesis of anionic phenylene monomers and their use in synthesizing anionic oligomers and polymers, with precise control of the position and number of anionic groups.