Water-Soluble 3-Hydroxyflavone Salts for Aqueous Sensing

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Solution Overview

Problem

Current 3-hydroxyflavone sensors lack specificity in detecting anions and cations, particularly in aqueous environments, and are not suitable for sensing DNA chains due to low water solubility and limited sensitivity to environmental changes.

Innovation Solution

Development of water-soluble 3-hydroxyflavone salts, such as N-(3-hydroxy-4'-flavonyl)-N,N,N-trimethylammonium sulphate, which exhibit enhanced fluorescence properties and ratiometric changes in response to anions, cations, and DNA structures, allowing for sensitive detection and differentiation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional 3-hydroxyflavone sensors are used, then fluorescence sensing capability is provided, but water solubility is low and detection specificity is poor

Engineering Contradiction:
Improvesensing capabilityVSAvoidwater solubility
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent modifies the chemical structure of 3-hydroxyflavone by introducing a quaternary ammonium group at the C-3 position, changing the molecular parameters to improve water solubility while maintaining fluorescence properties. This structural parameter change enables the sensor to function effectively in aqueous environments for detecting anions, cations, and DNA chains

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite structure by combining the 3-hydroxyflavone core with a quaternary ammonium group and various substituent groups (R1-R6). This composite molecular structure integrates the fluorescent properties of 3-HF with the water-solubility characteristics of the ammonium salt, resolving the contradiction between sensing capability and solubility

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If conventional 3-hydroxyflavone sensors are used, then fluorescence emission is observed, but detection precision and sensitivity to environmental changes are limited

Engineering Contradiction:
Improvefluorescence emissionVSAvoiddetection precision
Core Design Contradiction:
Illumination intensityVSMeasurement precision

Solution Approach 1:

The patent introduces specific functional groups at defined positions (R1-R6 substituents) to create local variations in the molecular structure that enhance sensitivity to specific analytes. The quaternary ammonium group at C-3 provides localized positive charge density that specifically interacts with anions, while other substituents can be tailored for cation or DNA detection, improving measurement precision without compromising overall fluorescence emission

Inventive Principle:
Principle #3Local quality

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 water-soluble 3-hydroxyflavone salts demonstrate efficient sensing capabilities for anions, cations, and DNA chains, providing clear emission bands and ratiometric quenching patterns, enabling effective identification and potential applications in bio-sensing and environmental monitoring.

Implementation Method 1

3-Hydroxyflavones (3-HF) are important fluorescent sensors due to their excited state intramolecular proton transfer (ESIPT) property originated from their normal (N*) and phototautomer forms (T*)

Methodology Applied
Scientific EffectExcited state intramolecular proton transfer (ESIPT):

Implementation Method 2

This property provides 3-HF with well separated two emission bands on fluorescent spectroscopy, resulting from their excited normal and tautomeric forms, intensities of which are sensitive to their environment, including polarity and hydrogen bonding perturbations

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentEP3055294B1Fluorophore 3-hydroxyflavone
Publication Date: 2019.04.10 TUBITAK
  • EP3055294B1 patent drawingFigure 1A~1B
  • EP3055294B1 patent drawingFigure 2~3
  • EP3055294B1 patent drawingFigure 4~5

AI summary

The present invention discloses the syntheses of new 3-hydroxyflavone salts with defined structures, which are suitable for sensor applications for sensing anions, cations, DNA chains and organic compounds soluble in highly polar solvent like water.