Amide-Containing Electrochromic Polymers for Aqueous Compatibility

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Solution Overview

Problem

Current electrochromic devices based on inorganic metal oxides and soluble small molecules lack versatility in color tuning, switching speed, and ease of processing, and hydrophobic conjugated polymers used in these devices pose health and environmental hazards due to expensive and hazardous electrolytes, while aqueous-compatible polymers with minimal polar substitutions are difficult to purify and characterize.

Innovation Solution

Introduction of amide-containing side chains in conjugated electrochromic polymers, such as ProDOT, which enables compatibility with both organic and aqueous electrolytes, reducing the number of polar groups required and enhancing electrochemical stability and redox activity, with specific examples like ProDOT-N(H)EtHx and ProDOT-N(Butyl)2 showing reversible switching in aqueous ammonium chloride electrolytes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If hydrophobic conjugated polymers are used in electrochromic devices, then electrochromic performance is achieved, but health and environmental hazards increase due to expensive and hazardous electrolytes

Engineering Contradiction:
Improveelectrochromic performanceVSAvoidhealth and environmental hazards
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameter of the polymer by introducing amide functional groups into the side chains, transforming the polymer from hydrophobic to hydrophilic character. This parameter change enables the polymer to work with benign aqueous electrolytes instead of hazardous organic electrolytes, eliminating the harmful effects while maintaining electrochromic performance

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces expensive and hazardous organic electrolytes with cheap and environmentally friendly aqueous electrolytes (water-based). This substitution uses simpler, less expensive materials that are safer for the environment and human health, while still achieving the desired electrochromic function

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Adaptability or versatility

If multiple polar functional groups are incorporated to design aqueous electrolyte compatible conjugated polymers, then aqueous compatibility is achieved, but purification and characterization difficulty increases

Engineering Contradiction:
Improveaqueous electrolyte compatibilityVSAvoidpurification and characterization
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

Instead of incorporating multiple polar functional groups throughout the polymer structure, the patent applies polar character locally by introducing a single amide functional group at specific positions in the side chain. This localized approach provides sufficient aqueous compatibility while minimizing the complexity associated with multiple polar substitutions, thereby easing purification and characterization

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent extracts the essential polar character needed for aqueous compatibility by isolating it in a single amide functional group, rather than distributing multiple polar groups throughout the structure. This extraction of the critical polar function simplifies the overall molecular structure and facilitates easier purification and characterization

Inventive Principle:
Principle #2Taking out (Extraction)

3Reliability

If inorganic metal oxides and soluble small molecules are used in electrochromic devices, then device stability is achieved, but color tuning versatility and switching speed are limited

Engineering Contradiction:
Improvedevice stabilityVSAvoidcolor tuning versatility
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent creates a composite electrochromic material by combining the stability of polymer structures with the versatility of conjugated systems. The resulting conjugated polymer with amide side chains integrates the mechanical stability and processability of polymers with the rich electrochromic properties of conjugated systems, achieving both device stability and color tuning versatility

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent introduces dynamic characteristics to the electrochromic system by utilizing the fast switching capabilities of conjugated polymers. The polymer structure allows for rapid electron delocalization and ion transport, enabling switching speeds that are significantly faster than inorganic metal oxides while maintaining device stability through the polymer's robust structure

Inventive Principle:
Principle #15Dynamics

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 amide-containing polymers exhibit excellent electrochromic performance and stability in both organic and aqueous electrolytes, with ProDOT-N(Butyl)2 demonstrating reversible switching and high contrast in aqueous ammonium chloride with minimal degradation, offering a greener and more efficient alternative for electrochromic devices.

Implementation Method 1

electrochromic polymers containing solubilizing side chains, where at least one side chain contains amide functional groups

Methodology Applied
Scientific EffectElectrochromism: Electrochromism

Implementation Method 2

exhibit excellent electrochromic performance and stability in both organic and aqueous electrolytes, with ProDOT-N(Butyl)2 demonstrating reversible switching

Methodology Applied
Scientific EffectRedox reactions: Redox Reactions

Data Source

PatentUS11220573B2Electrochromic polymers with amide-containing side chains and methods of fabricating same and electrochromic device containing same
Publication Date: 2022.01.11 AMBILIGHT INC
  • US11220573B2 patent drawing
  • US11220573B2 patent drawing
  • US11220573B2 patent drawing

AI summary

The present invention generally relates to electrochromic compounds, the synthesis method and the uses thereof, particularly to a family of conjugated electrochromic polymers containing solubilizing side chains, where at least one side chain contains amide functional groups. The disclosed conjugated electrochromic polymers with amide-containing side chains demonstrated excellent redox switching in not only organic but also aqueous media while maintaining high photo contrast. The presence of the amide groups is also beneficial when it comes to lower the oxidation onset potential of the polymers, making them attractive candidates for electrochromic in aqueous environment.