Stacking patterns of thieno[3,2‐b]thiophenes functionalized by sequential palladium‐catalyzed Suzuki and Heck cross‐coupling reactions

The crystal structures of three 5‐alkenyl‐2‐arylthieno[3,2‐b]thiophenes, namely 3,6‐dibromo‐5‐(4‐tert‐butylstyryl)‐2‐(naphthalen‐1‐yl)thieno[3,2‐b]thiophene, C28H22Br2S2, (I), 3,6‐dibromo‐5‐(4‐methylstyryl)‐2‐(naphthalen‐1‐yl)thieno[3,2‐b]thiophene, C25H16Br2S2, (II), and 3,6‐dibromo‐2‐(4‐tert‐butyl...

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Veröffentlicht in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2014-09, Vol.70 (9), p.895-899
Hauptverfasser: Nguyen, Hien, Nguyen Bich, Ngan, Dang, Tung T., Van Meervelt, Luc
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Sprache:eng
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Zusammenfassung:The crystal structures of three 5‐alkenyl‐2‐arylthieno[3,2‐b]thiophenes, namely 3,6‐dibromo‐5‐(4‐tert‐butylstyryl)‐2‐(naphthalen‐1‐yl)thieno[3,2‐b]thiophene, C28H22Br2S2, (I), 3,6‐dibromo‐5‐(4‐methylstyryl)‐2‐(naphthalen‐1‐yl)thieno[3,2‐b]thiophene, C25H16Br2S2, (II), and 3,6‐dibromo‐2‐(4‐tert‐butylphenyl)‐5‐(4‐methylstyryl)thieno[3,2‐b]thiophene, C25H22Br2S2, (III), have been determined in order to evaluate the geometry of the molecules. The π‐conjugated system containing the thieno[3,2‐b]thiophene skeleton, the ethylene bridge and the phenyl rings is almost planar. The aromatic ring directly attached to the thieno[3,2‐b]thiophene moiety is not coplanar with the thieno[3,2‐b]thiophene moiety itself due to steric hindrance of the bromo substituent. The crystal packings are characterized by π–π stacking [only for (II)] and C—Br...π interactions. The long axes of the molecules in (I) are oriented in two directions; for the two other structures the long axis is oriented in one direction only.
ISSN:2053-2296
0108-2701
2053-2296
1600-5759
DOI:10.1107/S2053229614018683