Abstract
In the title com-pound, C29H22N4O3, the carbazole system forms a dihedral angle of 68.45 (3)° with the mean plane of the bi-pyridine ring system. The bi-pyridine ring system, with two meth-oxy substituents, is approximately planar (r.m.s. deviation = 0.0670 Å), with a dihedral angle of 7.91 (13)° between the planes of the two pyridine rings. Intra-molecular C-H⋯O/N hydrogen bonds may promote the planarity of the bipyridyl ring system. In the pyridyl-substituted carbazole fragment, the pyridine ring is tilted by 56.65 (4)° with respect to the mean plane of the carbazole system (r.m.s. deviation = 0.0191 Å). In the crystal, adjacent mol-ecules are connected via C-H⋯O/N hydrogen bonds and C-H⋯π inter-actions, resulting in the formation of a three-dimensional (3D) supra-molecular network. In addition, the 3D structure contains inter-molecular π-π stacking inter-actions, with centroid-centroid distances of 3.5634 (12) Å between pyridine rings. The title com-pound exhibits a high energy gap (3.48 eV) and triplet energy (2.64 eV), indicating that it could be a suitable host material in organic light-emitting diode (OLED) applications.
Highlights
In the title compound, C29H22N4O3, the carbazole system forms a dihedral angle of 68.45 (3) with the mean plane of the bipyridine ring system
Intramolecular C—HÁ Á ÁO/N hydrogen bonds may promote the planarity of the bipyridyl ring system
Adjacent molecules are connected via C—HÁ Á ÁO/N hydrogen bonds and C— HÁ Á Á interactions, resulting in the formation of a three-dimensional (3D)
Summary
Carbazole-based organic small molecules have recently attracted much interest as organic light-emitting diodes (OLEDs) because of their high stability to the redox process, as well as their high triplet energy (ET ’ 3.0 eV) (Krucaite & Grigalevicius, 2019). A number of carbazole-based compounds have been developed as ligands to coordinate with heavy transition-metal ions, such as PdII and PtII (Fleetham et al, 2017). Bipyridine possesses a high triplet energy and a stable chelated coordination mode with respect to transition-metal ions, which makes it a suitable ligand for developing blue phosphorescent metal complexes (Zaen et al, 2019). Despite this advantage, reports of crystal structures of carbazole derivatives are still scarce. The luminescence properties of the title compound were examined via photophysical analysis
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