Rylene Dicarboximide Composition for Stable NIR Fluorescence
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Solution Overview
Problem
Current rylene-based dyes with emission in the NIR region suffer from low fluorescence quantum yields and stability issues, limiting their application in fluorescence and photovoltaic technologies, while other dyes with enhanced emission in this region lack thermal and chemical stability.
Innovation Solution
Development of π-extended, tetrachlorinated rylene dicarboximides with specific substituents that enhance absorption and emission in the NIR range, offering high fluorescence quantum yields and stability, suitable for use as fluorescent dyes, photovoltaic materials, and markers for liquids.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Illumination intensity
If rylene-based dyes are used for NIR emission, then absorption and fluorescence are bathochromically shifted, but fluorescence quantum yields decrease
Solution Approach 1:
The patent modifies molecular parameters by introducing specific substituents (electron-donating groups like alkoxy and alkyl groups) at defined positions of the rylene core, changing the electronic structure to enhance fluorescence quantum yield while maintaining NIR emission properties
Solution Approach 2:
The invention creates composite molecular structures by combining the rylene dicarboximide core with specific aromatic substituents, achieving a synergistic effect that simultaneously improves fluorescence quantum yield and maintains bathochromic shift for NIR applications
2Reliability
If other dye classes (BODIPY, squarine) are used for enhanced NIR emission, then fluorescence quantum yield improves, but thermal and chemical stability deteriorates
Solution Approach 1:
The patent applies local quality by introducing stabilizing imide groups at specific positions of the rylene core, creating regions of high thermal and chemical stability that protect the fluorescent chromophore while allowing enhanced NIR emission properties
3Illumination intensity
If π-extension is increased in rylene imides, then absorption and fluorescence are bathochromically shifted, but fluorescence quantum yield decreases
Solution Approach 1:
The patent segments the π-extension into controlled units by adding substituents at specific positions rather than extending the core continuously, allowing independent optimization of optical properties and fluorescence quantum yield
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 new compounds exhibit high solubility, stability, and detectability, enabling effective use in various applications including photovoltaics, security inks, and liquid markers with improved fluorescence quantum yields and thermal stability.
Implementation Method 1
fluorescent dye that absorbs light emitted from an irradiation source and emits light different from that of the irradiation source and having a wavelength in the range from 680 to 950 nm
Data Source
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AI summary
The present invention relates to compounds of the formula (I), a process for its preparation and its use as fluorescent dye that absorbs light emitted from an irradiation source and emits light different from that of the irradiation source and having a wavelength in the range from 680 to 950 nm; in photovoltaic applications; or as semiconductor in organic electronic applications; as laser dye, in an ink for machine readability and/or security applications or for the laser-welding of plastics; or for brand protection or as marker for liquids. The compounds of formula (I) may have a high fluorescence quantum yield, a high molar extinction coefficient, a high solubility and stability in the application medium, good storage stability and/or good detectability even in very small amounts in the correspondingly marked liquids.