Non-Dimerizing Electrochromic Compounds for Color Stability

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Solution Overview

Problem

Viologen derivatives in electrochromic devices exhibit uncontrolled changes in colored radical states due to intermolecular interactions, such as dimerization, leading to instability and temperature-dependent color changes, which affects the performance and reliability of these devices.

Innovation Solution

Development of non-dimerizing electrochromic compounds represented by specific formulas, which include substituted or unsubstituted alkyl, siloxyalkyl, hydroxyalkyl, or aralkyl groups, and anions like halides or borates, that prevent dimerization and maintain consistent color over a wide temperature range.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If viologen derivatives are used as electrochromic materials, then intense colored radical states are achieved, but uncontrolled dimerization occurs leading to temperature-dependent color changes and instability

Engineering Contradiction:
Improveintense colored radical stateVSAvoidcolor stability
Core Design Contradiction:
Illumination intensityVSStability of the object's composition

Solution Approach 1:

The viologen molecule is divided into two separate pyridinium units that are connected through a flexible spacer chain. This segmentation prevents the planar stacking and intermolecular interactions that cause dimerization, while each pyridinium unit retains its electrochromic functionality. The spacer acts as a physical barrier that segments the molecule into non-interacting units.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention introduces a third dimension (the spacer chain extending out of the plane) to break the two-dimensional stacking arrangement that leads to dimerization. By adding this dimensional element, the molecule adopts a three-dimensional conformation that prevents the face-to-face stacking responsible for temperature-dependent color changes.

Inventive Principle:
Principle #17Another dimension (Dimensionality change)

2Reliability

If viologen derivatives undergo dimerization, then colored radical states are formed, but the color changes become uncontrolled and temperature-dependent

Engineering Contradiction:
Improveperformance reliabilityVSAvoidtemperature independence
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The harmful dimerization property is extracted and removed from the system by modifying the molecular structure. The spacer chain extracts the planar stacking tendency, preventing dimer formation. This allows the viologen to maintain its electrochromic function without the harmful temperature-dependent color changes associated with dimerization.

Inventive Principle:
Principle #2Taking out (Extraction)

3Ease of operation

If conventional viologens are used, then electrochromic switching is achieved, but solubility changes and intermolecular interactions cause uncontrolled color variations

Engineering Contradiction:
Improveelectrochromic switchingVSAvoidcolor consistency
Core Design Contradiction:
Ease of operationVSManufacturing precision

Solution Approach 1:

Different parts of the viologen molecule are given different properties: the pyridinium rings provide electrochromic functionality, the spacer provides solubility and steric separation, and the substituent groups provide additional stability. This local differentiation of molecular regions allows each part to perform its specific function without interfering with others.

Inventive Principle:
Principle #3Local quality

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 non-dimerizing electrochromic compounds ensure temperature-independent color stability, enhancing the reliability and performance of electrochromic devices by preventing dimerization and maintaining consistent visible light absorption spectra across varying temperatures.

Implementation Method 1

Devices which rely on an electrochromic switch mechanism, i.e. reversible color change in the presence of an applied electric field or current

Methodology Applied
Scientific EffectElectrochromism: Electrochromism

Implementation Method 2

the device exhibits a λ max of greater than about 580 nm

Methodology Applied
Scientific EffectAbsorption spectroscopy: Absorption Spectroscopy

Data Source

PatentEP3256544B1Electrochromic compounds with improved color stability in their radical states
Publication Date: 2020.01.01 GENTEX CORP
  • EP3256544B1 patent drawingFigure 1
  • EP3256544B1 patent drawingFigure 2
  • EP3256544B1 patent drawingFigure 3

AI summary

The invention relates to an electrochromic device and uses thereof, wherein the electrochromic device includes an electrochromic compound with reduced intermolecular interactions resulting in uncontrolled color changes represented by Formula (I).