Synthesis, structure, and physical properties of 5,7,14,16-tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene

Abstract

A novel compound, 5,7,14,16-tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene (TBH), has been successfully synthesized through a retro-Diels-Alder reaction. Single-crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The HOMO-LUMO gap of TBH calculated from the difference between the half-wave redox potentials (E(1/2) (ox) =+0.40 eV and E(1/2)(red) =-1.78 eV) is 2.18 eV, which is in good agreement with the band gap (2.19 eV) derived from the UV/Vis absorption data. In addition, organic light-emitting devices using TBH as emitter have been fabricated. The results revealed that TBH is a promising red light-emitting candidate for applications in organic light-emitting diodes.