Disulfide Electrochromic Monomers for Tunable Conductive Polymers

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Solution Overview

Problem

Current methods for creating functionalized polymers that can be processed into various forms like fibers or films lack effective design and incorporation of buildable modules to adjust properties such as reactivity, hydrophobicity, and thermal stability, and interact well with solid substrates and biological systems.

Innovation Solution

A disulfide-containing electrochromic monomer and its reduced or derivative forms are synthesized through specific reactions with sulfur-containing compounds in polar solvents, which are then polymerized or crosslinked to produce polymers with enhanced electrochemical properties and functionalities.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If conventional methods are used to create functionalized polymers, then basic polymer properties can be achieved, but the ability to adjust reactivity, hydrophobicity, rigidity, thermal stability, and solvent resistance is limited

Engineering Contradiction:
Improveability to adjust polymer propertiesVSAvoidcomplexity of functional module design
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent divides the polymer system into modular components: a core polymer backbone and separate functional modules (disulfide-containing monomers with various R1 and R2 hydrocarbyl groups). These modules can be independently designed and combined to achieve desired properties like reactivity, hydrophobicity, and thermal stability without redesigning the entire polymer system.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The disulfide-containing monomer structure serves multiple functions simultaneously: it provides structural backbone elements, introduces tunable hydrophobicity through different R groups, enables crosslinking functionality through disulfide bonds, and offers sites for further functionalization. This multi-functionality reduces the need for separate specialized components.

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

2Adaptability or versatility

If functional modules are incorporated to improve polymer interactions with solid substrates and biological systems, then interaction capability is enhanced, but the ease of processing into fibers or films is reduced

Engineering Contradiction:
Improveinteraction with solid substrates and biological systemsVSAvoidprocessing into fibers or films
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent introduces functional groups at specific locations on the polymer chain (through R1 and R2 substituents on the disulfide-containing monomer) rather than uniformly throughout. This allows localized interaction capabilities with substrates or biological systems while maintaining the bulk polymer's processability into fibers or films.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent enables tuning of polymer properties by changing parameters such as the type of hydrocarbyl groups (R1 and R2), the degree of functionalization, and crosslinking density. These parameter adjustments allow optimization of both interaction capabilities and processability without fundamental redesign.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If disulfide-containing monomers are synthesized through nucleophilic substitution reactions with sulfur-containing compounds, then electrochemical properties are improved, but the synthesis complexity increases

Engineering Contradiction:
Improveelectrochemical propertiesVSAvoidsynthesis process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent uses pre-synthesized disulfide-containing monomers with defined structures before polymerization. This preliminary preparation of monomers with exact desired functionality simplifies the overall synthesis process compared to attempting to introduce disulfide groups after polymer formation, while ensuring consistent electrochemical properties.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent employs polar solvents as intermediaries to facilitate the nucleophilic substitution reactions between monomers and sulfur-containing compounds. These solvents mediate the reaction conditions to achieve high yields of disulfide-containing monomers with controlled purity, simplifying downstream processing.

Inventive Principle:
Principle #24Intermediary (Mediator)

4Reliability

If polymers are crosslinked to enhance stability and electrical conductivity, then electrochromic performance is improved, but the flexibility and processability are reduced

Engineering Contradiction:
Improveelectrical conductivity and electrochromic performanceVSAvoidflexibility and processability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent implements partial crosslinking through the disulfide-containing monomers rather than complete crosslinking. This partial action maintains sufficient electrical conductivity and electrochromic performance while preserving enough chain mobility and flexibility for processing into fibers or films, avoiding the brittleness of fully crosslinked systems.

Inventive Principle:
Principle #16Partial or excessive action

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 resulting polymers exhibit improved electrochemical properties, including high electrical conductivity and electrochromic performance, with the ability to be processed into thin films and modified for tailored interactions and stability, suitable for applications in devices like electrochromic devices, photovoltaics, and batteries.

Implementation Method 1

conducting a reduction of the disulfide-containing monomer of formula 1 with at least one reducing agent to form monomer of the formula 2

Methodology Applied
Scientific EffectReduction: Reduction

Implementation Method 2

the at least one monomer of the formula 1, the formula 2, or the formula 3 is incorporated to another monomer or a polymer under a polymerization reaction

Methodology Applied
Scientific EffectPolymerization:

Implementation Method 3

the at least one monomer of the formula 1, the formula 2, or the formula 3 is incorporated to another monomer or a polymer under a crosslinking reaction

Methodology Applied
Scientific EffectCrosslinking:

Implementation Method 4

The present disclosure presents a disulfide-containing electrochromic monomer

Methodology Applied
Scientific EffectElectrochromism: Electrochromism

Data Source

PatentUS11739179B2Disulfide-containing monomer, its reduced form, and its derivate, method to synthesize the same, and polymer containing the same
Publication Date: 2023.08.29 AMBILIGHT INC
  • US11739179B2 patent drawing
  • US11739179B2 patent drawing
  • US11739179B2 patent drawing

AI summary

The present disclosure presents a disulfide containing monomer, its reduced form, its derivative, the synthesis method of this disulfide containing monomer, and the polymer containing the monomers disclosed thereof