Azasilane Fluorescent Compounds for Red-Shifted Stable Detection
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Solution Overview
Problem
The synthesis of red shifted fluorescent dyes is challenging due to the difficulty in building up the carbocyclic framework, which can compromise brightness, photostability, and aqueous solubility.
Innovation Solution
Development of azasilane detectable compounds with specific substituents and linkers that enhance photostability and aqueous solubility, allowing for the detection of agents through bioconjugation with nucleotides or proteins.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Illumination intensity
If the carbocyclic framework is extended to achieve red shifted fluorescent dyes, then the absorption coefficient increases, but the brightness and photostability suffer
Solution Approach 1:
The patent changes the chemical composition parameters by replacing carbon atoms with silicon atoms in the carbocyclic framework, creating sila-fluorescein derivatives. This substitution modifies the electronic structure and optical properties, achieving red-shifted absorption while maintaining photostability through the unique properties of silicon-containing heterocyclic structures
Solution Approach 2:
The invention creates composite molecular structures by integrating silicon-containing heterocyclic rings with fluorescent dye frameworks. These composite structures combine the photostability advantages of silane compounds with the fluorescent properties of traditional dyes, resolving the contradiction between extended framework benefits and photostability maintenance
2Illumination intensity
If the carbocyclic framework is extended to achieve red shifted fluorescent dyes, then the absorption coefficient increases, but the aqueous solubility suffers
Solution Approach 1:
The patent introduces polar substituents and charged groups at specific positions on the sila-fluorescein core structure. These local modifications with hydrophilic groups (such as carboxyl, sulfonate, or ammonium groups) enhance aqueous solubility without significantly affecting the overall photophysical properties or the red-shifted absorption characteristic
Solution Approach 2:
By changing the molecular polarity parameters through substitution with hydrophilic groups and ionic moieties, the patent improves water solubility while preserving the extended conjugation system responsible for red-shifted absorption. The silicon atom substitution itself also contributes to improved solubility compared to all-carbon frameworks
3Illumination intensity
If the carbocyclic framework is built up for red shifted fluorescent dyes, then the absorption coefficient increases, but the synthesis becomes challenging
Solution Approach 1:
The patent employs a segmented synthetic approach where the sila-fluorescein core is constructed from separate heterocyclic building blocks that are coupled together. This modular synthesis strategy simplifies the overall process compared to traditional stepwise construction of extended carbocyclic frameworks, allowing for easier manipulation and purification at each stage
Solution Approach 2:
The invention uses stable heterocyclic intermediate structures containing silicon atoms as building blocks. These intermediaries facilitate the construction of the extended framework through well-established coupling reactions, avoiding the need for complex direct cyclization or rearrangement reactions that would increase synthesis difficulty
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 compounds provide improved photostability and solubility, enabling effective detection of agents using fluorescent dyes with enhanced performance.
Implementation Method 1
Rhodamine, acridine, and rhodol dyes are photostable with large absorption coefficients
Data Source
AI summary
Disclosed herein, inter alia, are silicon containing detectable compounds and methods of use thereof.