Water-Soluble Fluorescent Compound via Photochemical Reaction

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Solution Overview

Problem

There is a need for a water-soluble fluorescent compound with high single-photon and two-photon absorptive characteristics that can be efficiently prepared and used in various applications without toxicity.

Innovation Solution

A water-soluble fluorescent compound represented by specific formulas, derived from glycosylated resveratrol derivatives, is prepared through a photochemical reaction under UV irradiation, maintaining water solubility and exhibiting excellent fluorescent characteristics.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional fluorescent compounds are used, then fluorescent characteristics can be achieved, but water solubility is poor

Engineering Contradiction:
Improvefluorescent characteristicsVSAvoidwater solubility
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent combines a fluorescent core structure with water-soluble substituent groups (such as hydroxyl, carboxyl, or amino groups) to create a composite molecular structure that simultaneously provides fluorescent properties and water solubility. This allows the compound to function as both a fluorescent marker and a water-soluble substance for biological applications.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent introduces water-soluble functional groups at specific positions on the molecular structure while maintaining the core fluorescent system intact. This localized modification ensures that the fluorescent characteristics are preserved while adding the desired water solubility property to specific regions of the molecule.

Inventive Principle:
Principle #3Local quality

2Ease of manufacture

If single-photon absorption fluorescent substances are used, then simple excitation can be achieved, but two-photon absorption efficiency is insufficient for deep tissue imaging

Engineering Contradiction:
Improveexcitation simplicityVSAvoidtwo-photon absorption efficiency
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent modifies the molecular structure to optimize two-photon absorption cross-section by changing electronic parameters such as HOMO-LUMO energy gaps and electron delocalization. This allows the compound to efficiently absorb two photons simultaneously, enabling deep tissue imaging while maintaining reasonable excitation conditions.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If fluorescent compounds with high absorptive efficiency are developed, then imaging quality improves, but toxicity may increase

Engineering Contradiction:
Improveabsorptive efficiencyVSAvoidtoxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent optimizes the molecular structure to achieve high absorptive efficiency through controlled electron delocalization and appropriate HOMO-LUMO energy gaps, while simultaneously selecting biocompatible functional groups and molecular configurations that minimize toxicity. This balanced optimization allows high-performance fluorescent imaging with reduced biological harm.

Inventive Principle:
Principle #35Parameter changes

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 resulting compound has high efficiency in single-photon and two-photon absorptive characteristics, is non-toxic, and can be used in applications such as sunblocks, diagnostics, and display elements, offering advantages in fields requiring water-soluble fluorescent materials.

Implementation Method 1

a single-photon absorption fluorescent substance which absorbs only one photon under a strong laser to emit the fluorescence

Methodology Applied
Scientific EffectSingle-photon absorption: Absorption (EM radiation)

Implementation Method 2

a multi-photon absorption fluorescent substance which absorbs a plurality of photons to emits the fluorescence. The present invention relates to a new water-soluble fluorescent compound simultaneously having a single-photon absorption fluorescent feature as well as a multi-photon absorption fluorescent feature, in particular, 2-photon absorption fluorescent feature

Methodology Applied
Scientific EffectTwo-photon absorption: Absorption (EM radiation)

Implementation Method 3

Fluorescence refers to the phenomenon that a substance emits light only when the substance is irradiated

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Implementation Method 4

after a photochemical reaction of a conventionally known glycosylated derivative of resveratrol, for example, polydatin

Methodology Applied
Scientific EffectPhotochemical reaction: Photoluminescence

Data Source

PatentUSRE49223E1Water-soluble fluorescence compound and method for preparing the same
Publication Date: 2022.09.27 GLOBAL FRONTIER CENT FOR MULTISCALE ENERGY SYST
  • USRE49223E1 patent drawing
  • USRE49223E1 patent drawing
  • USRE49223E1 patent drawing

AI summary

The present invention provides a water-soluble fluorescent compound of resveratrone 6-O-β-glucoside [(E)-4-(8-hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)naphthalen-2-yl)but-3-en-2-one] and its derivatives of Formula I which have at least one water-soluble substituent, and a method for preparing the same by a photochemical reaction of resveratrol 3-O-β-glucoside and its derivatives of having Formula 3 which are not fluorescent.Said new water-soluble fluorescent compounds has single-photon absorptive characteristics and/or two-photon absorptive characteristics as well as no or little toxicity, and can be usefully utilized in fields that requires water-soluble fluorescent characteristics (diagnosis, fluorescent probe, in vivo imaging, display, etc.).