Substituted Rylene Derivatives Steep Absorption Band
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Existing rylene derivatives have limitations in their optical properties, particularly in the steepness of their absorption band, which affects their performance in various applications such as fluorescent dyes, NIR absorbers, and display applications.
Innovation Solution
Development of novel rylene derivatives with specific substituents such as ortho,ortho′-disubstituted aryl radicals and phenoxy radicals, which enhance the steepness of the absorption band and fluorescence properties, including the use of (thio)phenoxy radicals and cyclic amino groups to achieve improved optical properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional rylene derivatives are used, then the basic optical properties are maintained, but the steepness of the absorption band is insufficient
Solution Approach 1:
The patent applies local quality by introducing specific ortho,ortho′-disubstituted aryl radicals and phenoxy radicals at particular positions of the rylene skeleton. These localized substituent modifications selectively enhance the steepness of the absorption band at critical wavelengths without compromising the overall molecular structure or other optical properties. The substitution pattern creates localized electronic effects that sharpen the absorption features.
Solution Approach 2:
The patent employs parameter changes by systematically varying the substituents (aryl radicals with different R groups, phenoxy radicals with different R and R′ groups) to optimize the absorption band steepness. By adjusting the chemical parameters of the substituents (such as electron-donating or electron-withdrawing characteristics, steric effects), the absorption spectrum is tuned to achieve steeper bands while maintaining applicability in fluorescent dyes, near-infrared absorbers, and other optical applications.
2Use of energy by moving object
If rylene derivatives are modified to increase fluorescence quantum yield, then light utilization improves, but the complexity of the molecular structure increases
Solution Approach 1:
The patent applies local quality by placing fluorescent-enhancing substituents at specific positions on the rylene skeleton rather than uniformly modifying the entire molecule. The ortho,ortho′-disubstituted aryl radicals and phenoxy radicals are positioned to locally enhance fluorescence quantum yield through their electronic properties, while the rest of the molecular structure remains relatively simple and stable.
Solution Approach 2:
The patent uses composite materials by combining the rylene core with multiple types of functional substituents (aryl radicals with various R groups, phenoxy radicals with R and R′ groups). This composite approach integrates the fluorescent properties of the substituents with the structural stability of the rylene core, achieving high fluorescence quantum yield without excessive overall molecular complexity.
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 novel rylene derivatives exhibit distinctly steeper absorption bands, increased fluorescence quantum yield, and shifted absorption maxima to longer wavelengths, improving their utilization of incident light and performance in applications like coatings, plastics, and organic electronics.
Implementation Method 1
the steepness of their absorption band, which affects their performance in various applications such as fluorescent dyes and near-infrared absorbers
Implementation Method 2
their performance in various applications such as fluorescent dyes
Data Source
AI summary
Rylene derivatives of the general formula Iin which the variables are each defined as follows:Rylene is a polycyclic conjugated ring system which comprises at least one perylene unitmay comprise heteroatoms as ring atoms, may be functionalized by moieties comprising —CO— groups and/or may bear further substituents other than the A radicals;A is a radical of the formulaX is oxygen or sulfur;R are identical or different radicals:optionally substituted alkyl, cycloalkyl, aryl, hetaryl, —U-aryl where U is an —O—, —S—, —NR2—, —CO—, —SO— or —SO2— moiety, or C1-C12-alkoxy, C1-C6-alkylthio, —C≡CR2, —CR2═CR22, hydroxy, mercapto, halogen, cyano, nitro, —NR3R4, —NR3COR4, —CONR3R4, —SO2NR3R4, —COOR3 or —SO3R3;R′ are identical or different radicals: hydrogen or one of the R radicals;R2 is hydrogen or alkyl, where the R2 radicals may be the same or different when they occur more than once;R3, R4 are each independently hydrogen; optionally substituted alkyl, aryl or hetaryl;n is from 1 to 8.