2,3,7,8-Tetrakis(5-chlorothien-2-yl)pyrazino[2,3-g]quinoxaline–para-xylene (3/2)

Abstract

The asymmetric unit of the title compound, 3C26H10Cl4N4S4·2C8H10, contains 1.5 quinoxaline mol­ecules, one molecule having crystallographic inversion symmetry, and one para‐xylene solvent mol­ecule. The solvent molecules lie in channels along the [010] direction of the unit cell.

11,12-Dichlorodibenzo[a,c]phenazine

“…For the synthesis of the title compound, see: Bellizzi et al (2006). For the structures of similar compounds, see: Bellizzi et al (2006); Day et al (2002); Richards et al (2009).…”

“…To a 25 ml round bottom flask equipped with a reflux condenser was added 0.27 g (1.5 mmol) of 4,5-dichloro-1,2phenylenediamine, 0.27 g (1.3 mmol) of phenanthraquinone, and 10 ml of glacial acetic acid (Bellizzi et al, 2006) and the mixture was heated with refluxing for 6 h. After this time, the resulting yellow solution was concentrated under reduced pressure, and the product obtained was purified by recrystallization from methanol, producing 0.48 g of the title compound as a yellow solid (m.p. 273 °C; yield: 92%).…”

2-(2-Chlorophenyl)-3-(3,4-dimethoxyphenyl)quinoxaline

“…The quinoxaline moiety yields a wide variety of potential bidentate bridges in polymeric networks with silver, see: Patra et al (2007). For the synthesis and characterization of quinoxalines, see: Crundwell & Stacy (2005), of benzo[g]quinoxalines, see: Cantalupo et al (2006) and of pyrazino[2,3-g]quinoxalines, see: Bellizzi et al (2006).…”

“…The Crundwell lab has synthesized and characterized many quinoxalines (Crundwell et al, 2005), benzo[g]quinoxalines (Cantalupo et al, 2006), and pyrazino[2,3-g]quinoxalines (Bellizzi et al, 2006) as potential metal ligands. The title compound was formed by the condensation of two commercial products: 1,2-phenylenediamine and 2-chloro-3′,4′-dimethoxybenzil.…”

Substituent effect on the electronic properties of pyrazino[2,3-g] quinoxaline molecules

“…[4][5][6][7][8] The strong p-p interactions between the PQ moieties also make them highly crystalline in nature which is desirable for promoting efficient exciton migration and high charge carrier mobility. 4,[9][10][11][12][13] These intrinsic properties of PQ thus make it a good candidate for the development of low band gap and high mobility materials for 1 organic photovoltaics (OPVs). 4,8,11,[14][15][16] Varying substituents at the different positions of PQ using appropriate synthetic routes, allows the study of substituent effects on the overall electronic properties.…”