Novel meso-Polyarylamine-BODIPY Hybrids: Synthesis and Study of Their Optical Properties

A series of 14 meso-polyarylamine-BODIPY (borondipyrromethene) hybrids of the general structure A were synthesized. Two methods were used to prepare them. The first protocol involved a direct Liebeskind-Srogl cross-coupling of thiomethylbodipys 1-2 with arylaminoboronic acids (4 examples, 75-98%). The second method involves a two-step sequence: a Liebeskind-Srogl reaction to prepare 6 meso-bromoarylbodipys (58-83%) followed by a Suzuki coupling of these Br-containing BODIPYs with arylaminoboronic acids (10 examples, 44-84%). Seven of these derivatives displayed emission in the near-infrared region. The optical properties of compound 18 were rationalized in terms of its crystal structure.