Diindeno[1,2-b:2′,1′-n]perylene: a closed shell related Chichibabin's hydrocarbon, the synthesis, molecular packing, electronic and charge transport properties

Abstract

Diindeno[1,2-<i>b</i>:2',1'-<i>n</i>]perylene, a new derivative of the indenoacene family was synthesized, and its electronic, electrochemical, and electrical properties were investigated. This material has a closed shell electronic configuration which corresponds to a quinoidal structure with a low band gap of 1.35 eV. Molecular packing in the single crystal was studied by single-crystal X-ray structural analysis, and this information was subsequently used in the determination of the charge transfer integrals <i>via</i> density functional theory methods. The charge-carrier transport properties of the diindeno[1,2-<i>b</i>:2',1'-<i>n</i>]perylene-5,12-dione and diindeno[1,2-<i>b</i>:2',1'-<i>n</i>]perylene derivatives were investigated through the fabrication and characterization of field-effect transistors <i>via</i> both vacuum-deposited and solution-processed films, respectively. Diindeno[1,2-<i>b</i>:2',1'-<i>n</i>]perylene exhibited a field-effect behaviour with a hole mobility up to 1.7 × 10^-3 cm² V^-1 s^-1 when the active layer was solution-processed.