1456913-79-3Relevant academic research and scientific papers
Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties
Waghray, Deepali,Cloet, Arvid,Van Hecke, Kristof,Mertens, Stijn F. L.,De Feyter, Steven,Van Meervelt, Luc,Van Der Auweraer, Mark,Dehaen, Wim
, p. 12077 - 12085 (2013/09/23)
Diazadithia[7]helicenes were synthesized from the readily available building block ethyl 7-chloro-8-formylthieno[3,2-f]quinoline-2-carboxylate by a Wittig reaction-photocyclization strategy. The helicene core was functionalized by nucleophilic aromatic substitution with a variety of nucleophiles (e.g., O-, N-, and C-centered) and palladium-catalyzed reactions such as Suzuki coupling and Buchwald-Hartwig amination. Racemization studies confirmed that the enantiopure forms of these [7]helicenes are conformationally stable compared to their lower analogues. The solid-state structures of the novel diazadithia[7]helicenes were determined by single-crystal X-ray diffraction. The crystal structures of these azathia[7]helicenes show columnar stacking in antiparallel fashion. The HOMO-LUMO gaps of the new compounds were determined on the basis of electrochemical and optical measurements.
