Novel organoboron complexes with robust core: Synthesis, functionalization, and subcellular targeting

Area of Science:

• Organic Chemistry
• Materials Science
• Bioimaging

Background:

• Developing novel organoboron complexes for biological imaging presents synthetic challenges.
• Existing fluorescent dyes often lack the desired spectral properties or synthetic versatility.

Purpose of the Study:

• To establish a new molecular platform, boron indolin-3-one-pyrrol (BOIN3OPY), for the facile synthesis of versatile organoboron dyes.
• To create dyes with enhanced spectral properties and flexibility for functional regulation.

Main Methods:

• A two-step sequential reaction was employed to synthesize the core BOIN3OPY structure.
• Post-functionalization of the core allowed for the production of diverse dyes.
• Comparative analysis with standard BODIPY dyes was performed.

Main Results:

• A novel BOIN3OPY molecular platform was successfully synthesized.
• The resulting dyes exhibit an N,O-bidentate seven-membered ring center.
• These dyes demonstrate significantly redshifted absorption and larger Stokes shifts compared to BODIPY.

Conclusions:

• The BOIN3OPY platform offers a robust and flexible approach for designing novel organoboron dyes.
• The developed dyes possess advantageous spectral properties for biological imaging.
• This work expands the toolkit for creating tunable fluorescent probes.