Boronic Ester Metathesis for Polymer Functionalization

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Solution Overview

Problem

Current methods for functionalizing polymers lack efficient and versatile approaches, particularly in utilizing boronic ester metathesis reactions for introducing exchangeable pendant bonds and cross-linking points, which limits the modification of polymer properties and interactions with molecules of interest.

Innovation Solution

Development of novel boronic ester metathesis reactions and compounds with specific functional groups that allow for the grafting onto polymers, enabling exchange reactions and cross-linking, thereby modifying polymer compositions and behaviors.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If conventional polymer functionalization methods are used, then polymer modification is achieved, but the efficiency and versatility of introducing exchangeable pendant bonds and cross-linking points is limited

Engineering Contradiction:
Improveversatility of polymer functionalizationVSAvoidefficiency of introducing exchangeable pendant bonds
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The patent changes the chemical parameters of the reaction system by introducing boronic ester metathesis reactions that proceed under mild conditions with high efficiency. This allows for versatile functionalization of polymers with exchangeable pendant bonds while maintaining high productivity through quantitative reactions at room temperature.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The boronic ester functional groups introduced into the polymer structure serve multiple functions: they enable exchange reactions with various molecules, provide cross-linking capabilities, and allow for further chemical modifications. This multi-functionality resolves the contradiction by simultaneously improving versatility and efficiency.

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Productivity

If boronic ester metathesis reactions are implemented, then exchangeable pendant bonds and cross-linking points are efficiently introduced, but the complexity of the functionalization process increases

Engineering Contradiction:
Improveefficiency of introducing exchangeable pendant bondsVSAvoidcomplexity of functionalization process
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent uses boronic ester groups as intermediary functional groups that facilitate exchange reactions. These intermediaries enable efficient introduction of exchangeable pendant bonds through metathesis reactions with various compounds, achieving high productivity while maintaining relatively simple process conditions through room temperature reactions.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If quantitative reactions at room temperature are performed, then the polymer properties and interactions are improved, but the reaction conditions require precise control

Engineering Contradiction:
Improvequality of polymer functionalizationVSAvoidsimplicity of reaction conditions
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent optimizes reaction parameters to enable quantitative reactions at room temperature. By carefully selecting boronic ester compounds and controlling reaction conditions, the patent achieves high reliability in polymer functionalization while maintaining ease of operation through avoidance of extreme temperatures and pressures.

Inventive Principle:
Principle #35Parameter changes

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

Enables the creation of cross-linked polymer compositions with enhanced functionalization capabilities, allowing for improved polymer properties and interactions with molecules of interest, such as peptides and proteins, through quantitative and room-temperature reactions.

Implementation Method 1

The inventors discovered a novel boronic ester metathesis reaction and described: the preparation of a compound library implementing this novel reaction

Methodology Applied
Scientific EffectBoronic ester metathesis reaction: Chemical Bonding

Data Source

PatentUS11680074B2Compounds, functionalised dioxaborolane or dioxaborinane derivatives, method for preparing same and uses thereof
Publication Date: 2023.06.20 ECOLE SUPERIEURE DE PHYSIQUE & DE CHIM IND DE LA VILLE DE PARIS
  • US11680074B2 patent drawing
  • US11680074B2 patent drawing
  • US11680074B2 patent drawing

AI summary

The invention relates to functionalised dioxaborolane or dioxaborinane derivatives of formula (I), wherein R1 is covalently bonded to the boron atom by a carbon atom; one of R2, R3, R′3 or R4 is a radical of formula —X; or one of R1, R2, R3, R′3 or R4 is a radical of formula —X; and X is a functionalised radical. The invention relates to the method for preparing same and the uses thereof.