Ionic Perylene Bisimide Composition Against Concentration Quenching
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Solution Overview
Problem
Perylene bisimide derivatives suffer from concentration quenching and decreased luminescence quantum yield in high-concentration solutions and solid states due to hydrophobic interactions, limiting their use in applications requiring high dye concentrations.
Innovation Solution
Introduce a biphenyloxy group substituted with a water-soluble ionic substituent, such as a sulfo group, into each benzene ring of the dye to suppress aggregation through electrostatic repulsion, enhancing water solubility and luminescent properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Use of energy by moving object
If a perylene bisimide derivative with high fat-solubility is used, then luminescence quantum yield is high in dilute solutions, but aggregation occurs in high-concentration solutions due to hydrophobic effect leading to decrease in luminescence
Solution Approach 1:
The patent changes the chemical parameters of the perylene bisimide derivative by introducing ionic substituents (such as sulfonate groups) at specific positions on the molecule. This parameter change transforms the molecule from hydrophobic to hydrophilic, enabling high water solubility while maintaining luminescence properties even at high concentrations where aggregation would normally occur.
Solution Approach 2:
The patent creates a composite molecular structure combining the hydrophobic perylene bisimide core with hydrophilic ionic substituent groups. This composite structure allows the molecule to maintain its luminescent properties while simultaneously achieving high water solubility and resistance to aggregation through the hydrophilic exterior groups.
2Illumination intensity
If the concentration of dye is increased to improve luminescence intensity, then signal strength increases, but concentration quenching occurs leading to decrease in luminescence efficiency
Solution Approach 1:
The patent modifies molecular parameters by adding ionic groups that change the intermolecular interaction characteristics. This allows the system to operate at high dye concentrations without experiencing concentration quenching, thereby maintaining high luminescence efficiency even when total luminescence intensity needs to be high for application performance.
3Stability of the object's composition
If water-soluble substituents are introduced to improve solubility, then aggregation is suppressed, but luminescence quantum yield may decrease due to steric hindrance or electronic effects
Solution Approach 1:
The patent applies local quality by placing ionic substituents at specific peripheral positions on the perylene bisimide core rather than modifying the entire molecule uniformly. This localized modification approach suppresses aggregation through hydrophilic groups while minimizing steric hindrance and electronic effects on the luminescent core, thereby preserving high luminescence quantum yield.
Solution Approach 2:
The ionic substituent groups act as intermediary elements between the hydrophobic luminescent core and the aqueous environment. These intermediary groups provide the necessary hydrophilicity for water solubility and aggregation suppression while being positioned and designed to minimize their negative impact on the electronic properties of the luminescent core.
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 luminescent compound exhibits high luminescence quantum yield even under high concentration conditions, suitable for applications in luminescent compositions, thin films, and particles, with improved stability and efficiency.
Implementation Method 1
Introduce a biphenyloxy group substituted with a water-soluble ionic substituent, such as a sulfo group, into each benzene ring of the dye to suppress aggregation through electrostatic repulsion
Implementation Method 2
Perylene bisimide derivatives, which are polycyclic aromatic compounds having a wide π-conjugate plane, exhibit luminescence derived from π-π* transition
Data Source
AI summary
A luminescent compound has a structure represented by a general formula (1),wherein R represents a luminescent dye skeleton, X represents an ionic substituent, and L represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, or an NH group.