Crystal Structure of 1,4,5,8-Tetrapentylanthracene

Abstract

Solid-state packing effects play an important role in the performance of electronic and photonic materials. 1 We recently found that the introduction of alkyl side chains onto the anthracene nucleus at the 1-, 4-, 5-, and 8-positions brought about drastic changes in both the packing and solid-state fluorescence properties. 2 The length of the alkyl side chains affected not only the packing arrangement and the solid-state fluorescence, but also the molecular geometry. Thus, the molecular structures were classified into plane (the ethyl derivative), semi-chair (the propyl derivative), and chair (the hexyl derivative) forms. To investigate the effects of the alkyl side-chain length systematically, investigations on the butyl and pentyl derivatives remained. Herein we report on an X-ray analysis of the pentyl derivative, 1,4,5,8-tetrapentylanthracene. The title compound was synthesized by our recently reported procedure using 2,5-dipentylfuran, 1,2,4,5-tetrabromobenzene, and n-BuLi. 2 Colorless crystals suitable for X-ray analysis were obtained by slow evaporation of a hexane solution at room temperature. All measurements were made on a Rigaku/MSC Mercury CCD diffractometer with Mo-Ka (l = 0.71073 Å) at 223 K. A structure determination was carried out using the program SIR2004. 3 All of the non-hydrogen atoms were refined anisotropically by full-matrix least-squares on F 2 using SHELXL97. 4 H atoms were placed at calculated positions, with C-H distances of 0.94-0.98 Å, and treated as riding atoms, with Uiso(H) = 1.2 Ueq(C) for Csp 2 and CH2, and Uiso(H) = 1.5 Ueq(C) for CH3. All calculations were performed using the WinGX

Spectroscopic investigation (FT-IR and FT-Raman), vibrational assignments, HOMO–LUMO analysis and molecular docking study of 1-hydroxy-4,5,8-tris(4-methoxyphenyl) anthraquinone

“…C 8 -C 9 (1.4161 Å) and C 4 -C 5 (1.4180 Å) bond lengths are about 0.01Å longer than those in 7-methoxy-2-methyl-4,5-dihydroxyanthraquinone [50]. The C-C bond lengths in the anthraquinone ring of the title compound are in the range of 1.3790-1.5012 Å, the values of which are similar to those of other substituted anthracenes [51]. Allouchi et al [52] reported the bond lengths and bond angles of the anthracene ring as C 7 -C 8 =1.4872 Å, C 7 -C 4 =1.4822 Å, C 5 -C 4 =1.3892 Å, C 5 -C 10 =1.4772 Å, C 10 -C 9 =1.4892 Å, C 9 -C 8 =1.3842Å and C 2 -C 3 -…”