Phenanthro[b]-Fused BODIPYs through Tandem Suzuki and Oxidative Aromatic Couplings: Synthesis and Photophysical Properties.

A new synthetic method to build phenanthrene-fused BODIPYs through tandem Suzuki couplings on readily available 2,3,5,6-tetrabromoBODIPYs, followed by an intramolecular oxidative aromatic coupling mediated by iron(III) chloride is reported. This efficient synthesis allows a very straightforward approach for tuning the absorption and emission of BODIPYs in the red/NIR range. These resultant phenanthrene-fused BODIPYs exhibit strong absorption (extinction coefficients up to 2.2 × 105 M-1 cm-1) and emission in the near-infrared (NIR) range (688-754 nm) with excellent photostabilities. Substituted groups on the resultant phenanthrene rings have significant impact on the photophysical properties of these phenanthrene-fused BODIPYs.

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