Spacer-Linked Dimeric Dyes for Reduced Fluorescence Quenching
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Solution Overview
Problem
Existing dimeric and polymeric fluorescent and colored dyes do not achieve the desired increase in brightness due to intramolecular fluorescence quenching, limiting their effectiveness in aqueous environments for biomolecule analysis.
Innovation Solution
Development of water-soluble dyes with covalently linked fluorescent and/or colored moieties separated by a linker, reducing intramolecular fluorescence quenching and enhancing brightness.
Engineering Contradictions & Design Principles
Engineering 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 occurs and the desired brightness increase is not achieved
Solution Approach 1:
The dye molecule is segmented into multiple fluorescent moieties (at least two) connected by spacer groups, allowing each moiety to function independently while contributing to overall brightness without significant quenching interactions
Solution Approach 2:
Spacer groups act as intermediary elements between fluorescent moieties, providing physical separation that prevents intramolecular quenching while maintaining the dimeric or polymeric structure necessary for enhanced brightness
2Illumination intensity
If multiple fluorescent moieties are closely linked to form dimers or polymers, then the theoretical brightness should increase, but the spatial proximity causes intramolecular fluorescence quenching
Solution Approach 1:
The spacer groups extend the molecular structure in spatial dimensions, creating three-dimensional separation between fluorescent moieties that prevents quenching while maintaining optical coherence for enhanced brightness
3Illumination intensity
If known dimeric and polymeric dyes are synthesized without adequate spacing, then the structural complexity increases to achieve brighter signals, but intramolecular quenching reduces the actual fluorescence output
Solution Approach 1:
The spacer group length and composition are optimized to specific parameters that balance structural complexity with fluorescence performance, achieving enhanced brightness while maintaining reasonable molecular complexity through systematic variation of spacer characteristics
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 dyes exhibit increased molar brightness, allowing for intense coloration and fluorescence, enabling visual detection of analytes without prior illumination, and providing a variety of colors and wavelengths for biomolecule analysis.
Implementation Method 1
dimeric and polymeric compounds comprising two or more fluorescent and/or colored moieties have been prepared in anticipation that such compounds would result in brighter dyes. However, as a result of intramolecular fluorescence quenching, the known dimeric and polymeric dyes have not achieved the desired increase in brightness
Data Source
AI summary
Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I):or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, R4, R5, L1, L2, L3, L4, M, m and n are as defined herein. Methods associated with preparation and use of such compounds are also provided.