NIR II Organic Dyes for Biocompatible Biological Imaging
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Solution Overview
Problem
Current NIR II fluorophores are limited by toxicity, insolubility, and accumulation in the body, making them unsuitable for therapeutic applications, and there is a lack of efficient, tunable, and biocompatible materials that can absorb and emit in the NIR II region for applications like biological imaging and solar cells.
Innovation Solution
Development of novel NIR II organic dyes through C—H bond functionalization, specifically using indolizine and xanthene derivatives like RhIndz, which are water-soluble, biocompatible, and have tunable properties, allowing for intense absorption and emission in the NIR II range, suitable for imaging and optoelectronic devices.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Use of energy by moving object
If nanoparticles, nanotubes, or quantum dots are used as NIR II fluorophores, then quantum efficiency is improved, but biocompatibility and excretion properties deteriorate due to accumulation in spleen and liver
Solution Approach 1:
The patent employs small molecule organic dyes that are metabolizable and excretable rather than persistent nanoparticles. These small molecules can be processed by biological systems and eliminated through natural metabolic pathways, avoiding the accumulation issues that plague nanoparticle-based fluorophores in the spleen and liver.
Solution Approach 2:
The patent modifies molecular parameters of organic dyes including incorporating water-soluble groups and adjusting molecular weight to optimize both photophysical properties and biocompatibility. By changing these molecular parameters, the dyes achieve high quantum efficiency while maintaining solubility and metabolic compatibility.
2Illumination intensity
If polymethine dyes are used for NIR II imaging, then absorption and emission in NIR II region is achieved, but toxicity increases
Solution Approach 1:
The patent creates composite molecular structures combining xanthene cores with indolizine or carbazole units. This composite approach allows the molecule to achieve extended conjugation for NIR II emission while incorporating biocompatible functional groups that reduce toxicity compared to traditional polymethine dyes.
Solution Approach 2:
The patent uses metabolizable organic small molecules instead of persistent polymethine dyes. These molecules can be broken down and eliminated by biological systems, reducing long-term toxicity concerns while maintaining NIR II imaging capabilities.
3Productivity
If C—H bond functionalization is used for dye synthesis, then synthetic efficiency and tolerance of functional groups are improved, but selectivity deteriorates due to multiple C—H bonds in substrates
Solution Approach 1:
The patent employs directed C—H activation at specific positions of indolizine or carbazole rings by using directing groups or catalysts that recognize specific molecular locations. This allows selective functionalization at desired positions despite the presence of multiple C—H bonds in the substrate molecules.
Solution Approach 2:
The patent uses transition metal catalysts as intermediaries to mediate the C—H activation process. These catalysts provide selective binding to specific C—H bonds through coordination chemistry, enabling regioselective functionalization while maintaining high synthetic efficiency and tolerance for various functional groups.
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 new dyes enable real-time, cost-effective biological imaging and enhanced solar cell performance, with potential for night vision and secure OLED displays, while being non-toxic and easily metabolizable, addressing the limitations of existing NIR II materials.
Implementation Method 1
fluorescent dyes that absorb and emit in the near infrared II (NIR II) range of the electromagnetic spectrum
Implementation Method 2
novel emissive dye materials and compositions that absorb and emit light in the NIR II region
Data Source
AI summary
In one aspect, the disclosure relates to fluorescent dyes that absorb and emit in the near infrared II (NIR II) range of the electromagnetic spectrum, methods of making same, compositions comprising same and methods of using the compositions to perform imaging on biological samples, and optoelectronic devices using the dyes. The dyes are small organic molecules that are inexpensive and facile to produce, can be water-soluble, have tunable properties, and are biocompatible and/or possess low toxicity.