Synthesis, Molecular Packing and Semiconductor Properties of V‐Shaped N‐Heteroacene Dimers

Abstract

AbstractThis article presents two groups of V‐shaped π‐scaffolds that consist of two N‐heteroacene units fused with either a rigid or flexible eight‐membered ring. These rigid and flexible N‐heteroacene dimers were synthesized through the condensation of tetraphenylenetetraone with the corresponding diamine and the Pd‐catalyzed cross‐coupling of tetrabromodibenzo[a,e]cyclooctatetraene with the corresponding diamine, respectively. A comparison of electronic structures and properties of the two groups of V‐shaped N‐heteroacene dimers shows subtle difference between the rigid and flexible eight‐membered ring linkers in forming extended π‐systems. X‐ray crystallography of these V‐shaped molecules has revealed interesting π‐π interaction modes, which are dependent on the central connecting units and substituting groups. These π‐π interactions between the V‐shaped π‐scaffolds have enabled the molecules to function as organic semiconductors in solution‐processed field effect transistors.