One-Step Synthesis of a 2,2'-Directly-Linked Perylene Dimer from a 2,5,8,11-Tetraborylated Perylene

Abstract

One-step Suzuki-Miyaura cross-coupling reaction of 2, 5, 8, 11-tetra-borylated perylene with 2, 6-bis(trifluoromethyl)bromo-benzene gave 2, 2'-linked perylene dimer for the first time in 7.3 % yield under the standard conditions. The single-crystal X-ray structure exhibits three independent dimers in the unit cell, reflecting the low rotational energy around 2, 2'-linkage. Excited state properties of 2, 2'-dimer were compared with the corresponding 3, 3'-linked congener. The facile synthetic method developed in this study could be a general route to access polycyclic aromatic hydrocarbon oligomers linked at less reactive positions.