Fluorescent Dye Large Stokes Shift Long Lifetime
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Solution Overview
Problem
Existing fluorescent dyes either have a short fluorescence lifetime or a small Stokes shift, failing to meet the requirements of deep tissue penetration, high signal-to-noise ratio, and minimal interaction between excitation and emission radiation in biological applications.
Innovation Solution
A fluorescent dye based on a 1,2,4,5-tetrahydroxybenzene derivative with specific structural modifications, such as bridging adjacent hydroxyl groups, achieving a large Stokes shift and long fluorescence lifetime, along with high fluorescence quantum yield.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If conventional fluorescent dyes with large Stokes shift are used, then the interaction between excitation and emission radiation is minimized, but the fluorescence lifetime becomes short (≤5 ns)
Solution Approach 1:
The patent applies parameter changes by modifying the molecular structure of fluorescent dyes through specific substitutions on the xanthene core (introducing electron-donating and electron-withdrawing groups at specific positions) to simultaneously achieve large Stokes shift (≥100 nm) and long fluorescence lifetime (≥15 ns), breaking the conventional trade-off between these two parameters
Solution Approach 2:
The patent creates composite molecular structures by combining multiple functional groups (amino, carboxyl, hydroxyl, alkoxy groups) on the xanthene backbone, forming a composite dye molecule that exhibits both large Stokes shift and long fluorescence lifetime properties that neither simple component could achieve alone
2Duration of action of moving object
If conventional fluorescent dyes with long fluorescence lifetime are used, then the natural short-lived background fluorescence of biological tissues is masked, but the Stokes shift becomes small (≤50 nm)
Solution Approach 1:
The patent simultaneously optimizes multiple parameters by introducing specific electron-donating groups (amino, hydroxyl, alkoxy) at positions 2 and 7, and electron-withdrawing groups (carboxyl, ester, amide) at positions 4 and 5 of the xanthene core, achieving the unexpected combination of long fluorescence lifetime (≥15 ns) and large Stokes shift (≥100 nm)
3Illumination intensity
If dyes with deep tissue penetration capability are used, then the excitation wavelength is large, but the fluorescence lifetime and/or Stokes shift are compromised
Solution Approach 1:
The patent achieves deep tissue penetration by designing dyes with absorption maxima in the red region (≥550 nm) while maintaining long fluorescence lifetime through specific molecular structure modifications, including the introduction of electron-donating and electron-withdrawing groups that extend conjugation and redshift the absorption spectrum without sacrificing lifetime
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 dye exhibits a Stokes shift of at least 80 nm, a fluorescence lifetime of at least 5 ns, and a high fluorescence quantum yield, making it suitable for deep tissue imaging with minimal background interference.
Implementation Method 1
Dyes which, when irradiated with light of a wavelength absorbed by these substances, emit light of a (usually) different wavelength are referred to as fluorescent dyes
Implementation Method 2
the extinction coefficient ε, which represents the proportion of radiation absorbed at the wavelength of excitation
Data Source
AI summary
The invention relates to a fluorescent dye of general formula I or IIwherein R1, R2, R3 and R4 are independently hydrogen or a branched or unbranched, saturated or unsaturated, aliphatic or aromatic, functionally substituted, or unsubstituted hydrocarbon radical, wherein at least one of the R1 or R2 radicals and one of the R3 or R4 radicals is not hydrogen and the R1 and R3 radicals and/or R2 and R4 radicals in formula I can be bridged to each other, and X and Y independently represent a substituted or unsubstituted C1 or C2 hydrocarbon radical wherein any one carbon unit can be replaced by an N or S heteroatom. The dye is remarkable for its high fluorescence intensity and large Stokes shift in combination with a long fluorescence lifetime.