Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

Abstract

C 24 H 15 NO, monoclinic, P2 1 /n (no. 14), a = 10.3161 ( CCDC no.: 1579090The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of material1-Pyrenecarboxaldehyde (230 mg, 1.0 mmol) and methanol (30 mL) were placed in a round-bottom flask and stirred at room temperature for 10 min. Then 4-acetylpyridine (145 mg, 1.2 mmol) and NaOH (5 mol/L, 10 mL) were added. The resulting reaction mixture was stirred at room temperature for 30 min. The mixture was extracted with CH 2 Cl 2 . The solvent was removed under reduced pressure to give the crude product, which was purified by column chromatog- raphy (petroleum ether:ethyl acetate = 1:4) to give the title compound as a red solid (isolated yield 50%). The isolated product was crystallized from CHCl 3 to give red single crystals. Experimental detailsAll hydrogen H atoms were positioned geometrically and refined using a riding model, with d(C-H) = 0.93 Å and U iso (H) = 1.2 U eq (C). DiscussionPyrenes are considered to be excellent organic fluorophores and they are applied as environmental probes with distinct morphology and tunable emission in various micro environments due to their polarity dependent vibronic emission, high charge carrier mobility, fluorescence lifetime and chemical stability [3][4][5][6]. Up to now, numerous pyrene derivatives with good fluorescence properties have been reported. For example, (2-pyrene-1-yl-vinyl)pyridine has reversible luminescence and nonlinear optical properties [7], 4-((pyren-1-yl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one exhibits notable aggregation induced emission (AIE) phenomena in both solution and solid state [5]. 1-Methyl benzoate-pyrene displays pure blue monomer photoluminescence and electrogenerated chemiluminescence emissions in non-aqueous media [8]. In order to search for more pyrene-based compounds, in this paper we report a new one.There is one molecule in the asymmetric unit (cf. the figure). Bond lengths and angles are all in the expected ranges [9]. The non-H atoms of the pyrene ring and pyridine ring are nearly planar, respectively. But the pyrene unit is not coplanar