Synthesis, Properties, and Semiconducting Characteristics of BF2 Complexes of β,β-Bisphenanthrene-Fused Azadipyrromethenes.

Three novel π-extended BF2 complexes of β,β-bisphenanthrene-fused azadipyrromethenes containing nine fused rings have been synthesized on the basis of a tandem Suzuki coupling reaction on readily available 2,6-dibromoazaBODIPYs followed by an intramolecular oxidative aromatic coupling mediated by iron(III) chloride. These resultant BF2 complexes exhibit strong absorption (extinction coefficients up to 2.4 × 105 M-1 cm-1) and emission in the near-infrared (NIR) range (790-816 nm) with excellent photo and thermal stabilities. The hole mobility of the thin-film field-effect transistors of these dyes fabricated by a solution process reaches up to 0.018 cm2 V-1 s-1.