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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Soccer goes BOXing: synthetic access to novel [6:0] hexakis[(bisoxazolinyl)methano]fullerenes
Stefan M Seifermann1, Céline Réthoré, Thierry Muller
1Institute of Organic Chemistry and DFG Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Abstract:
The syntheses of [6:0] hexakis[(bisoxazolinyl)methano]fullerenes are presented. Two derivatives could be directly obtained using conditions developed by the Sun group. For the remaining products, a two stage protocol had to be developed. All compounds we obtained in synthetically useful scales and were purified via column chromatography with standard achiral phase. These new fullerene adducts bear six metal-chelation sites which are aligned in the three orthogonal space directions and are disposed on a completely rigid scaffold. First experiments indicate that the generation of six-fold metal-complexes is possible with these structures. This makes them very appealing as ligands in asymmetric catalysis and as building blocks in higher supra-molecular assemblies.
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