Imide Derivative Suppressing Concentration Quenching
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Solution Overview
Problem
Perylene bisimide derivatives exhibit a high luminous quantum yield in dilute solutions but suffer from concentration quenching in high-concentration solutions or solids, limiting their use in fluorescent dyes for particles and thin films.
Innovation Solution
Introducing a bulky substituent at specific positions in the perylene bisimide derivative to sterically prevent π-π stacking, thereby suppressing concentration quenching. This approach can be applied to both perylene bisimide and naphthaleneimide derivatives.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If perylene bisimide derivative is used in high-concentration solution or solid state, then the quantity of substance increases, but the luminous quantum yield is remarkably lowered due to concentration quenching
Solution Approach 1:
The patent applies local quality by introducing bulky substituents at specific positions (bay regions) of the perylene bisimide core structure. This localized modification creates steric hindrance that prevents π-π stacking between adjacent molecules, thereby suppressing concentration quenching while maintaining the overall high-concentration or solid-state formulation capability
Solution Approach 2:
The patent changes the molecular structure parameters by adding bulky substituent groups (such as tert-butyl, phenyl, naphthyl groups) with specific steric properties. These parameter changes in molecular geometry and steric bulk directly affect the intermolecular spacing and stacking behavior, enabling high concentration without quenching
2Loss of energy
If bulky substituent is introduced to suppress concentration quenching, then the luminous quantum yield is improved, but the device complexity increases
Solution Approach 1:
The patent segments the molecule into a rigid perylene bisimide core and separate bulky substituent groups attached at bay regions. This segmentation allows the core to maintain its luminescent function while the substituents independently provide steric protection against aggregation, resolving the complexity issue by functional separation
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 imide derivatives with bulky substituents maintain a high luminous quantum yield even in high-concentration solutions and solid states, making them suitable for use in luminescent compositions, thin films, and particles.
Implementation Method 1
concentration quenching can be suppressed by introducing a bulky substituent at a specific position in the perylene bisimide derivative such that the bulky substituent sterically prevents π-π stacking of the perylene bisimide derivative
Implementation Method 2
The perylene bisimide derivative, which is a polycyclic aromatic compound having a large π-conjugated plane, shows luminescence derived from the π-π* transition
Data Source
AI summary
An imide derivative has a structure represented by general formula (1) below.In the general formula (1), a plurality of R1 each independently represent a hydrogen atom or a substituent. At least one R1 represents a group having 4 to 30 carbon atoms. A benzene ring or naphthalene ring optionally further has a substituent, and * represents a position of a substituent that the benzene ring or naphthalene ring optionally has.