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A series of β,β'-bicyclo-3,5-diaryl-BODIPYs were synthesized from the corresponding β,β'-bicyclo-3,5-diiodo-BODIPYs ( 1a,b ) via Pd(0)-mediated Suzuki cross-coupling reactions in 82-92% yields. Subsequent aromatization with DDQ afforded the corresponding β,β'-dibenzo-aryl-BODIPYs, which showed red-shifted absorptions and emissions in the near-IR range. The dibenzo-appended BODIPYs showed characteristic 1 H-, 13 C-, 11 B- and 19 F-NMR shifts, and nearly planar conformations by X-ray crystallography.

Synthesis and spectroscopic properties of β,β′-dibenzo-3,5,8-triaryl-BODIPYs