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π-Fused bis-BODIPY as a candidate for NIR dyes
Mitsunori Nakamura1, Hiroyuki Tahara, Kohtaro Takahashi
1Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan.
Organic & Biomolecular Chemistry
|July 14, 2012
Summary
New benzene-fused bis-(borondipyrromethene)s (bis-BODIPYs) were synthesized for near-infrared applications. These novel compounds exhibit strong absorption and fluorescence in the NIR region with minimal visible light absorption, making them ideal for advanced optical technologies.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Borondipyrromethene (BODIPY) dyes are known for their strong fluorescence.
- Developing NIR-emitting dyes is crucial for applications in imaging and sensing.
- π-conjugated systems offer tunable optical properties.
Purpose of the Study:
- To synthesize novel benzene-fused bis-BODIPY derivatives.
- To achieve intensive absorption and strong fluorescence in the near-infrared (NIR) region.
- To minimize absorption in the visible region for specific applications.
Main Methods:
- Synthesis of bicyclo[2.2.2]octadiene-fused (BCOD-fused) bis-BODIPYs from pyrrolo[3,4-f]isoindole precursors.
- Retro-Diels-Alder reaction of BCOD-fused bis-BODIPYs to yield benzene-fused bis-BODIPYs.
- Spectroscopic characterization (absorption, emission, quantum yield) of the synthesized compounds.
Main Results:
- A syn-bis-benzoBODIPY derivative showed strong absorption and emission bands at 775 nm and 781 nm, respectively, with an absolute quantum yield of 0.36.
- This syn-isomer exhibited absorption more than 5.0 times stronger in the NIR region compared to the visible region.
- Anti-bis-benzoBODIPY derivatives displayed absorption and emission maxima exceeding 840 nm.
Conclusions:
- Benzene-fused bis-BODIPYs are effectively synthesized via a retro-Diels-Alder strategy.
- These novel chromophores demonstrate significant potential for NIR fluorescence applications due to their strong NIR absorption and emission.
- The synthetic approach allows for tuning of optical properties, with isomers showing distinct NIR emission profiles.
