Abstract
The title compound, C17H7F8N3O, was obtained via the reaction of 1-azido-2,3,4,5,6-penta-fluoro-benzene with 4,4,4-tri-fluoro-1-(p-tol-yl)butane-1,3-dione using tri-ethyl-amine as a base catalyst and solvent. The dihedral angles between the penta-fluoro-phenyl (A), triazole (B) and p-tolyl (C) rings are A/B = 62.3 (2), B/C = 43.9 (3) and A/C = 19.1 (3)°. In the crystal, the mol-ecules are linked by C-H⋯F and C-H⋯O hydrogen bonds as well as by aromatic π-π stacking inter-actions into a three-dimensional network. To further analyse the inter-molecular inter-actions, a Hirshfeld surface analysis was performed.
Highlights
Compounds with perfluoroaromatic motifs are of interest for the design of fluorescence materials, including their application in optoelectronic devices (Funabiki et al, 2021; Feng et al, 2021; Moseev et al, 2019; Kandhadi et al, 2018; Lukeset al., 2016; Wang et al, 2013; Matsui et al, 2008)
The perfluorobiphenyl moiety was used as an electron acceptor for new donor–acceptor compounds with thermally activated delayed fluorescence (TADF) applied for the fabrication of TADF-based OLEDs (Danyliv et al, 2021; Hladka et al, 2018)
The pentafluorophenyl ring and the heterocyclic ring are twisted relative to each other by 62.3 (2) because of the significant steric hindrance of the trifluoromethyl group attached to C7
Summary
Compounds with perfluoroaromatic motifs are of interest for the design of fluorescence materials, including their application in optoelectronic devices (Funabiki et al, 2021; Feng et al, 2021; Moseev et al, 2019; Kandhadi et al, 2018; Lukeset al., 2016; Wang et al, 2013; Matsui et al, 2008). A literature survey showed limited data on the reaction of perfluorophenylazide in the synthesis of 1,2,3-triazoles The pentafluorophenyl ring and the heterocyclic ring are twisted relative to each other by 62.3 (2) because of the significant steric hindrance of the trifluoromethyl group attached to C7 This dihedral angle is significantly smaller than the angle of 87.1 between the 4-nitrophenyl and triazole rings in the structure of 1-[5methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]ethanone (VI) (Vinutha et al, 2013) but considerably larger than the analogous angle between aromatic rings in the structures of 3-(4fluorophenyl)-1-[1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]prop-2-en-1-one (39.6; El-Hiti et al, 2018), (4-methylphenyl)(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)methanone (44.5; Li et al, 2014), 1-[1-(4-chlorophenyl)-5-methyl-1H1,2,3-triazol-4-yl]ethanone (45.6) and 1-[1-(4-bromophenyl)5-methyl-1H-1,2,3-triazol-4-yl]ethanone (47.1) (Zeghada et al, 2011). Symmetry codes: (i) x þ 12; Ày þ 12; Àz þ 1; (ii) Àx þ 12; Ày þ 1; z þ 12; (iii) Àx þ 1; y À 12; Àz þ 32
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