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- Title
From Chrysene to Double [5]Helicenes.
- Authors
Bock, Harald; Huet, Stephanie; Dechambenoit, Pierre; Hillard, Elizabeth A.; Durola, Fabien
- Abstract
Glyoxylic functionalization of chrysene by Friedel-Crafts acylation with ethyl chloroglyoxylate or by bromination followed by substituent exchange enables the formation of bis[5]helicene-tetracarboxylates and tetracarboxdiimides through Perkin reactions and palladium-catalyzed cyclizations. Tetrasubstituted bishelicenic dichrysenoanthracenes and dinaphthochrysenes are thus obtained from chrysene in four to six steps. In the cyclization to dinaphthochrysenes, a rearrangement of the conjugated carbon skeleton is identified as side reaction. In solution, the diimides form mixtures of M, P- and M, M/ P, P-diastereomers, which equilibrate at room temperature when the helices are distant but equilibrate only upon heating when the helices are close and acting in concert. The nonplanar arene geometry allows close π-contacts in two dimensions between neighboring molecules in the crystal.
- Subjects
CHRYSENE; HELICENES; FRIEDEL-Crafts reaction; BROMINATION; PERKIN reaction; AROMATIC compounds; RING formation (Chemistry)
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 5, p1033
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403341