Tröger's Base Polymers for Gas Separation Membranes
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Solution Overview
Problem
The synthesis of ladder-type polymers of intrinsic microporosity (PIMs) is limited by the availability of sterically hindered contortion sites, which restricts the development of high-performance gas separation membranes with optimal permeability and selectivity.
Innovation Solution
Intrinsically microporous ladder-type Tröger's base polymers are developed, incorporating a combination of W-shaped CANAL-type and V-shaped Tröger's base building blocks, which provide high BET surface areas and bimodal pore size distributions, enabling the formation of robust and efficient gas separation membranes.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If sterically hindered contortion sites are incorporated to create microporosity and improve gas permeability, then gas separation performance is enhanced, but the availability of suitable building blocks is limited and synthesis becomes more difficult
Solution Approach 1:
The patent changes the chemical parameters by introducing Tröger's base units with specific stereochemistry and W-shaped CANAL motifs, creating a unique molecular architecture that achieves high microporosity while maintaining solution processability through controlled polymerization parameters
Solution Approach 2:
The patent creates a composite molecular structure combining two different building block types (Tröger's base and CANAL motifs) within the same polymer chain, achieving synergistic effects that improve both gas separation performance and mechanical properties compared to single-building-block polymers
2Manufacturing precision
If rigid contortion centers are used to frustrate polymer chain packing and create high surface area, then gas selectivity improves, but the polymer becomes more brittle and mechanically weaker
Solution Approach 1:
The patent applies local quality by distributing rigid contortion centers at specific intervals along the polymer chain rather than making the entire chain uniformly rigid, maintaining high surface area and selectivity while preserving chain flexibility and mechanical strength through softer connecting segments
Solution Approach 2:
The patent introduces asymmetry through the chiral Tröger's base units and W-shaped CANAL motifs, creating non-symmetric polymer chains that pack less efficiently to maintain microporosity while the asymmetric structure also provides unique gas transport pathways that enhance selectivity without sacrificing mechanical integrity
3Temperature
If ladder-type structure is adopted to achieve high thermal stability and rigidity, then thermal stability improves, but the polymer requires complex polycondensation reactions with limited building blocks
Solution Approach 1:
The patent segments the ladder-type polymer structure into repeating units based on Tröger's base and CANAL motifs, allowing systematic construction of the rigid ladder framework through controlled polycondensation while maintaining solution processability through appropriate end-group functionalization
Data Source
AI summary
Embodiments of the present disclosure feature an intrinsically microporous ladder-type Tröger's base polymer including a repeat unit based on a combination of W-shaped CANAL-type and V-shaped Tröger's base building blocks, methods of making the intrinsically microporous ladder-type Tröger's base polymer, and methods of using the intrinsically microporous ladder-type Tröger's base polymer to separate a chemical species from a fluid composition including a mixture of chemical species. Embodiments of the present disclosure further include ladder-type diamine monomers for reacting to form a Tröger's base in situ, and methods of making the ladder-type diamine monomers using catalytic arene-norbornene annulation.