5,7,12,14-Tetraphenyl-Substituted 6,13-Diazapentacenes as Versatile Organic Semiconductors: Characterization in Field Effect Transistors

Abstract

We report the synthesis of 5,7,12,14-tetraphenyl-substituted 6,13-dihydro-6,13-diazapentacene and its fully aromatic 6,13-diazapentacene congener. Both arylated diazapentacenes were characterized by X-ray crystallography to investigate their solid-state structures and by UV–vis spectroscopy and cyclic voltammetry to unveil their electronic properties. The experimental results are complemented with theoretical investigations. The semiconductor properties of both diazapentacene derivatives were assessed in organic field-effect transistors, whereby the fully aromatized compound showed comparably less abundant n-type behavior.

4nπ Stable Multitasking Azapentacene: Acidochromism, Hole Mobility, and Visible Light Photoresponse

“…As shown in Figure , the azapentacene core adopts almost a planar structure with two phenyl substituents appended thereof. The dihedral angles between the plane containing the azapentacene core and the two planes A and B associated with two phenyl pendants were found to be 67.75 and 66.77°, respectively, indicating weak electronic communications between the π-conjugated core and its substituents …”

“…The dihedral angles between the plane containing the azapentacene core and the two planes A and B associated with two phenyl pendants were found to be 67.75 and 66.77°, respectively, indicating weak electronic communications between the π-conjugated core and its substituents. 29 To gain a deep insight into the electronic structure of this new 24π dihydrotetrazapentacene, nucleus-independent chemical shift (NICS) and anisotropy of the induced current density (ACID) calculations were conducted (vide infra). 30,31 NICS calculation provides information about the individual ring current of a conjugated molecule.…”

Silver cation tagged on 5,7,12,14-tetraphenyl-6,13-diazapentacene and its dihydro-form

“…41 Both tetraphenyl-substituted diazapentacene derivatives were recently synthesised and their semiconductor properties have been critically assessed as well. 12,13…”

Polyazaacene and Cyclazaacene Precursors Synthesized by Dehydration Condensation from a Versatile Bis‐α‐diketone Unit Having an Anthracene Skeleton

“…They have been attracting attention because of their potential application in organic electronics and materials science. [16][17][18][19][20][21][22][23] The incorporation of nitrogen atoms into the π-systems of acenes adds dominant enrichments to their electronic properties. [24][25] Substantial efforts have been devoted to investigating azapentacene derivatives.…”

“…Azaacenes are acene analogs that contain nitrogen atoms in their carbon‐based molecular skeletons. They have been attracting attention because of their potential application in organic electronics and materials science [16–23] . The incorporation of nitrogen atoms into the π‐systems of acenes adds dominant enrichments to their electronic properties [24–25] .…”