Syntheses, crystal structures, luminescence, Hirshfeld surface analyses and thermal properties of biphenyl carbazole derivatives

• Published in: Journal of molecular structure 2021-12, Vol.1245, p.131018, Article 131018
• Main Authors: Tang, Gui-Mei, Xi, Yu-Rong, Sun, Wen-Chao, Wang, Yong-Tao, Kang, Ming-Hui, Gao, Xiang
• Format: Article
• Language: English
• Subjects: Biphenyl carbazole; Crystal structures; Hirshfeld surface analyses; Infrared spectra; Iodination; UV-Vis spectra; X-ray diffraction
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.131018

•Two biphenyl carbazole-based derivatives exhibit high thermal stabilities, where the decomposition temperature are 298 and 368 °C, respectively.•The luminescent properties can be meditated by the substituted groups and the dihedral angles between the biphenyl and carbazole-yl rings.•The emission peaks are relative to the intermolecular contacts of Br∙∙∙C, I∙∙∙C and C∙∙∙C. Two biphenyl carbazole-based derivative, namely, 9-(4′‑bromo-[1,1′-biphenyl]-4-yl)-9H-carbazole (1) and 9-(4′‑bromo-[1,1′-biphenyl]-4-yl)-3,6-diiodo-9H-carbazole (2) have been obtained. Compound 2 was prepared through the iodination on 9-(4′‑bromo-[1,1′-biphenyl]-4-yl)-9H-carbazole (1). Two compounds were characterized by FI-IR, UV–Vis spectra, elemental analyses and single-crystal X-ray diffraction. Compound 1 crystallizes in the formation of the space group P21/n. There exist CH⋯π stacking interactions among aromatic rings. Compound 2 belongs to the space group P-1, and it occurs intermolecular CH⋯π and π⋯π packing interactions among aromatic rings. Thermogravimetric analyses (TGA) of two compounds exhibit high thermal stabilities, in which the decomposition temperature for 1 and 2 are 298 and 368 °C, respectively. Additionally, the maximal peaks of compounds 1 and 2 are 386 and 410 nm, respectively. The Hirshfeld analyses reveal that the intermolecular contacts of Br∙∙∙C, I∙∙∙C and C∙∙∙C are responsible for the maximal bands. [Display omitted] Two biphenyl carbazole-based derivative were characterized by FI-IR, UV–Vis spectra, elemental analyses and single-crystal X-ray diffraction. Compound 1 crystallizes in the formation of the space group P21/n and P-1. There exist CH•••π stacking interactions among aromatic rings. Thermogravimetric analyses (TGA) of two compounds exhibit high thermal stabilities. The maximal peaks of compounds 1 and 2 are 386 and 410 nm, respectively. The Hirshfeld analyses reveal that the intermolecular contacts of Br∙∙∙C, I∙∙∙C and C∙∙∙C are responsible for the maximal bands.