3,5-Diiodo-BODIPYs were prepared from a common tetrahydroisoindole pyrrole and were functionalized on 3,5-positions. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) has been developed as an effective catalyst for symmetrical and unsymmetrical Pd-catalyzed Suzuki coupling reactions, and versatile boronic acids were connected on BODIPY's 3,5-positions. An oxidative condition (2,3-dichloro-5,6-dicyano-1,4-benzoquinone in refluxing toluene) was then applied to give dibenzo-appended-BODIPYs in 30 minutes. Photophysical studies show dibenzo appended BODIPYs' UV-vis absorbance and fluorescent emission bands red shifted approximately 100 nm into near-IR region after aromatization, with higher quantum yields. The newly synthesized near IR BODIPYs have three handles to further functionalize for potential conjugations with biomolecules and optimize their photophysical properties, for example, quantum yields enhancements, red-shifts of UV-vis and emission wavelengths and better water solubilities.

Design and synthesis of near-IR BODIPYs via cross-couplings and benzo-fusions

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.