A Three-Step Synthesis of 1,7-Diazaperylene and Derivatives

Abstract

Abstract1,7-Diazaperylene and various derivatives were synthesised in an upscaleable route from 1,5-diaminoanthraquinone and its Meerwein­ reaction with acrylonitrile and subsequent cyclisation with ammonia. The application of tert-butyl alcohol as the solvent led to a significant improvement in the Meerwein reaction.

1,7‐Diazaperylene in Organic Field Effect Transistors

“…This suggests a lower tendency of this material towards H‐aggregate formation. This is further corroborated by the differences in molecular packing as shown by comparison of the crystal structures reported for perylene [28,33,34] and 1,7‐diazaperylene [14] . While perylene in its α form shows an arrangement of closely spaced slipped‐parallel dimers, no such dimeric arrangement was observed for 1,7‐diazaperylene.…”

“…Since the isolation of two different modifications of solid 1,7‐diazaperylene has been reported earlier, [14] the optical properties of 1,7‐diazaperylene thin films processed from different solutions were investigated to characterize a possible occurrence and influence of different modifications in solid films. The PLE and PL spectra of films prepared by spincoating from solutions of 1,7‐diazaperylene in chloroform and in a toluene/acetone mixture (volumetric ratio 4 : 1) are shown in Figure 4.…”

“…The planarity of 1,7‐diazaperylene in contrast to the twisted geometry of the latter allows a more densely packing in solids as is shown by comparing the x‐ray crystal structures of the two [3] . In fact, heteroaromatic molecules that are planar are densely packed, with density of about 1.4 g/cm 3 , arranging themselves in a modified herringbone structure [14] . These special properties make this heterocyclic compound interesting for applications in material chemistry where claims such as in LED devices [15,16] were described.…”

“…[3] In fact, heteroaromatic molecules that are planar are densely packed, with density of about 1.4 g/cm 3 , arranging themselves in a modified herringbone structure. [14] These special properties make this heterocyclic compound interesting for applications in material chemistry where claims such as in LED devices [15,16] were described. However, the inefficient synthesis of 1,7-diazaperylene limited both its technical usefulness and further research.…”

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…A scalable synthesis of 1,7-diazaperylene and its alkyl derivatives ( 43.3a – f , Scheme 43 ) was reported by Langhals and co-workers. 72 Diazotization of 1,5-diaminoanthraquinone 43.1 provided the isolable and stable double diazonium salt 43.2 . The subsequent copper-catalyzed Meerwein arylation reaction with acrylonitrile provided the corresponding dialdehyde, which was used without purification in a condensation with NH 3 .…”