Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties

Waghray, D. and Cloet, A. and Van Hecke, K. and Mertens, S.F.L. and De Feyter, S. and Van Meervelt, L. and Van Der Auweraer, M. and Dehaen, W. (2013) Diazadithia[7]helicenes: Synthetic exploration, solid-state structure, and properties. Chemistry - A European Journal, 19 (36). pp. 12077-12085. ISSN 0947-6539

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Abstract

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.

Item Type:
Journal Article
Journal or Publication Title:
Chemistry - A European Journal
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600
Subjects:
ID Code:
132989
Deposited By:
Deposited On:
22 Apr 2019 14:00
Refereed?:
Yes
Published?:
Published
Last Modified:
07 Apr 2020 06:10