Aza-Triangulenium Fluorescent Dyes with Hydroxy Quenching
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Solution Overview
Problem
Current fluorescent dyes for sensing analytes, particularly pH, lack improved photophysical properties such as sensitivity and stability, limiting their effectiveness in monitoring and determining analyte concentrations.
Innovation Solution
Development of substituted aza-triangulenium fluorescent dyes with a hydroxy group attached to an aryl as a quenching group, which exhibit photoinduced electron transfer (PET) responsive properties, allowing for sensitive detection of analytes like H+, Na+, K+, Ca2+, O2, CO2, and metal ions across a wide pH range.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional fluorescent dyes are used for sensing analytes, then detection capability is provided, but sensitivity and photostability are insufficient
Solution Approach 1:
The patent employs composite fluorescent dye structures combining aza-triangulenium core with specific aryl-hydroxy quenching groups. This composite design integrates the photostable triangulenium scaffold with PET-active quenching moieties, achieving both high photostability and enhanced sensitivity through the synergistic combination of structural components.
Solution Approach 2:
The patent systematically modifies molecular parameters including substituent types (electron-donating/withdrawing groups), hydroxy group positions (ortho, meta, para), and counterions to optimize the balance between photostability and sensitivity. These parameter changes tune the PET efficiency and fluorescence quantum yield while maintaining structural stability.
2Measurement precision
If fluorescent dyes with improved sensitivity are developed, then detection precision increases, but photostability may be compromised
Solution Approach 1:
The fluorescent dye is segmented into functionally distinct modules: a photostable aza-triangulenium core responsible for fluorescence emission, and separate aryl-hydroxy quenching groups attached at specific positions. This segmentation allows independent optimization of each module's properties - the core provides photostability while the quenching groups provide sensitivity through PET mechanisms.
3Reliability
If new fluorescent dye structures are synthesized to improve performance, then sensitivity and stability are enhanced, but device complexity increases
Solution Approach 1:
The aza-triangulenium core structure serves multiple functions simultaneously: it provides the fluorescent chromophore, ensures photostability through its rigid aromatic system, and offers multiple attachment points for quenching groups. This multi-functionality reduces the need for additional auxiliary structures, managing complexity while achieving enhanced performance.
4Adaptability or versatility
If conventional dyes are used for broad analyte detection, then versatility is limited, but maintaining simple structures is preferred
Solution Approach 1:
The patent introduces local quality variations by placing identical hydroxy groups at different positions (ortho, meta, para) on the aryl rings, and by using different electron-donating/withdrawing substituents at specific locations. These localized modifications create dyes with tuned properties for detecting different analytes (H+, metal ions, pH) while maintaining the overall modular structure.
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 dyes demonstrate enhanced sensitivity and photostability, enabling reliable monitoring of analyte concentrations, even under harsh conditions, with modified quenching characteristics and long-term stability.
Implementation Method 1
When a PET responsive fluorescent molecule absorbs a photon, an excited electronic state is created and an electron transfer prevents the excited molecule from emitting a photon. Thus, the fluorescence of the dye is quenched.
Implementation Method 2
When a PET responsive fluorescent molecule absorbs a photon, an excited electronic state is created
Implementation Method 3
Fluorescence offers an ideal solution for detection and sensing applications, as readout signals of probes or sensors containing fluorescent molecules are done by light.
Data Source
Figure 1a1~1a2
Figure 1b1~1b2
Figure 1c
AI summary
The present invention relates to a new class of substituted aza-triangulenium fluorescent dyes having a hydroxy group attached to an aryl as quenching group. The new substituted aza-triangulenium fluorescent dyes may be attached to a linker, conjugated to carrier molecule such as e.g. a protein, a nucleic acid, a lipid, or a saccharide, or deposited or immobilised on solid support materials. The substituted aza-triangulenium fluorescent dyes are useful for various purposes, including use in sensors for monitoring or determining the concentration of analytes, such as H+(pH), Na+, K+, Ca2+, O2, CO2, H2O2, ionic strength, redox potentials, metal ions,and metabolites.