Abstract
In the title compound, C27H18N2, the mean planes of the pendant benzene rings are approximately perpendicular to one another, making a dihedral angle of 79.3 (5)°; the indeno-[1,2-b]quinoxaline ring system (r.m.s. deviation = 0.1197 Å) is twisted with respect to the pendant benzene rings by 70.0 (4) and 67.6 (3)°. Weak aromatic π-π stacking [centroid-centroid separation = 3.628 (2) Å] and C-H⋯π inter-actions occur in the crystal.
Highlights
Some quinoxaline-based N-heteroacenes show a narrow band-gap, high thermal stability and aligned film morphology, which can be applied as the hole transport layers in quantum dot light-emitting diodes (QLEDs) (Bai et al, 2015)
As part of our work in this area, we report the synthesis and crystal structure of the title indeno[1,2-b]quinoxaline derivative
The pendant C1–C6 and C8–C13 benzene rings are nearly perpendicular to one another [dihedral angle = 79.3 (5)] while the indeno[1,2-b]quinoxaline fused ring system (N1–N2/C7,C14–C27) is twisted with respect to the C1–C6 and C8–C13 benzene rings, subtending dihedral angles of 70.0 (4) and 67.6 (3), respectively
Summary
Some quinoxaline-based N-heteroacenes show a narrow band-gap, high thermal stability and aligned film morphology, which can be applied as the hole transport layers in quantum dot light-emitting diodes (QLEDs) (Bai et al, 2015). As part of our work in this area, we report the synthesis and crystal structure of the title indeno[1,2-b]quinoxaline derivative. The pendant C1–C6 and C8–C13 benzene rings are nearly perpendicular to one another [dihedral angle = 79.3 (5)] while the indeno[1,2-b]quinoxaline fused ring system (N1–N2/C7,C14–C27) is twisted with respect to the C1–C6 and C8–C13 benzene rings, subtending dihedral angles of 70.0 (4) and 67.6 (3), respectively. Weak Cg6Á Á ÁCg6i aromatic – stacking interactions [centroid–centroid separation = 3.628 (2), slippage = 1.717 A , symmetry code: (i) = 1 À x, 1 À y, 1 À z; where Cg6 is the centroid of the C22–C27 benzene ring] link the molecules into inversion dimers and weak C—HÁ Á Á interactions link the dimers (Table 1, Fig. 2). Cg2 and Cg3 are the centroids of the N1/N2/C20–C23 and C1–C6 rings, respectively
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