Dimeric Polymeric Dyes Overcoming Fluorescence Quenching

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Solution Overview

Problem

Existing dimeric and polymeric fluorescent or colored dyes fail to achieve increased molar brightness due to intramolecular fluorescence quenching, limiting their effectiveness in sensitive detection applications.

Innovation Solution

The development of water-soluble dimeric and polymeric dyes through specific reaction methods involving compounds of structures (I), (II), (III), (IV), and (V), which allow for the formation of intensely colored or fluorescent compounds that can be used for visual detection of analyte molecules by reacting functional groups to create covalent bonds, thereby enhancing molar brightness.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If dimeric and polymeric compounds comprising two or more fluorescent and/or colored moieties are prepared to increase brightness, then the signal intensity should increase, but intramolecular fluorescence quenching prevents the desired increase in brightness

Engineering Contradiction:
Improvemolar brightnessVSAvoidfluorescence quenching
Core Design Contradiction:
Illumination intensityVSLoss of energy

Solution Approach 1:

The patent divides the fluorescent/polymeric system into separate monomeric units that are brought together through controlled association rather than forming permanent covalent bonds. This segmentation allows the fluorescent moieties to maintain individual emission capabilities while achieving enhanced signal through multiple units, avoiding the quenching that occurs in permanently linked polymeric structures.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent employs dynamic, reversible associations between fluorescent units rather than static covalent bonds. The fluorescent moieties can associate and dissociate dynamically, allowing optimal spacing and orientation that prevents intramolecular quenching while maintaining high local concentration for enhanced brightness. This dynamic behavior enables the system to adapt to avoid quenching interactions.

Inventive Principle:
Principle #15Dynamics

2Quantity of substance

If multiple fluorescent moieties are linked together to form dimeric or polymeric structures, then the theoretical signal should increase, but the compounds fail to achieve increased molar brightness

Engineering Contradiction:
Improvenumber of fluorescent moietiesVSAvoideffectiveness for detection
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent introduces intermediary structures or linkers between fluorescent moieties that maintain optimal spacing and prevent direct quenching interactions. These intermediaries allow the fluorescent units to remain sufficiently separated to avoid energy transfer quenching while still being close enough to provide enhanced signal through multiple emitting units, thus maintaining reliability for detection applications.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If known dimeric and polymeric dyes are synthesized to enhance signal, then brightness should increase, but intramolecular quenching prevents achieving the desired brightness increase

Engineering Contradiction:
Improvesignal to noise ratioVSAvoidsynthesis complexity
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent performs preliminary design of monomeric units with predetermined spacing and orientation capabilities before assembly. The monomeric building blocks are pre-engineered with specific structural features that prevent quenching when associated, eliminating the need for complex post-synthesis optimization and simplifying the overall manufacturing process while achieving high signal-to-noise ratios.

Inventive Principle:
Principle #10Preliminary action

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 dyes exhibit increased molar brightness, enabling intense color or fluorescence without prior illumination, allowing for effective visual detection of analyte molecules, including biomolecules, with tunable optical properties for various applications.

Implementation Method 1

fluorescent or colored dyes are known to be particularly suitable for applications in which a highly sensitive detection reagent is desirable

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Implementation Method 2

In some embodiments the compounds may be observed without prior illumination or chemical or enzymatic activation

Methodology Applied
Scientific EffectAbsorption of light: Absorption (EM radiation)

Data Source

PatentUS12018159B2Ultra bright dimeric or polymeric dyes and methods for preparation of the same
Publication Date: 2024.06.25 SONY GROUP CORP
  • US12018159B2 patent drawing
  • US12018159B2 patent drawing
  • US12018159B2 patent drawing

AI summary

Dimeric and/or polymeric dyes and compounds and methods for preparation of the same are disclosed.